过氧化苯甲酰:修订间差异
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ThomasYehYeh(留言 | 贡献) 我把Benzoyl peroxide翻譯為中文,用來補充原來翻譯版本過氧化苯甲醯不足之處。敬請指教。 标签:HTML註解 加入不存在模板 |
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{{medical}} |
{{medical}} |
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{{Chembox |
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{{Infobox drug |
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| Name = 过氧化苯甲酰 |
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| |
| image = Benzoyl-peroxide.svg |
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| width = |
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| ImageFile = Benzoyl-peroxide.svg |
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| alt = |
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| ImageFile2 = Benzoyl-peroxide-3D-balls.png |
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| image2 = Benzoyl-peroxide-from-xtal-3D-bs-17.png |
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| ImageFile3 = Benzoyl_peroxide_sample.jpg |
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| width2 = |
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| IUPACName = diphenylperoxyanhydride |
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| alt2 = |
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| OtherNames = 过氧化二苯甲酰;过氧二苯甲酰;过氧苯甲酰;过氧化苯酰;过氧化苯酸 |
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| caption = [[鍵線式|骨架式]] (上圖) [[球棍模型]] (下圖) |
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| Abbreviations = BPO |
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| Section1 = {{Chembox Identifiers |
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<!-- Clinical data --> |
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| InChI=1/C14H10O4/c15-13(11-7-3-1-4-8-11)17-18-14(16)12-9-5-2-6-10-12/h1-10H |
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| pronounce = |
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| CASNo = 94-36-0 |
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| tradename = Benzac、Panoxyl及其他 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Drugs.com = {{Drugs.com|ppa|benzoyl-peroxide}} |
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| EC-number = 202-327-6 |
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| MedlinePlus = a601026 |
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| ChemSpiderID = 6919 |
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| DailyMedID = Benzoyl peroxide |
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| PubChem = 7187 |
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| pregnancy_AU = <!-- A/B1/B2/B3/C/D/X --> |
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| ATCCode_prefix = D10 |
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| pregnancy_AU_comment = |
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| ATCCode_suffix = AE01 |
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| pregnancy_category= |
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| ATC_Supplemental = QD11[http://www.whocc.no/atcvet/database/index.php?query=QD11AX90 AX90] |
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| routes_of_administration = [[外用藥物]] |
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| RTECS = DM8575000 |
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| class = |
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| SMILES = O=C(OOC(=O)c1ccccc1)c2ccccc2 |
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| ATC_prefix = D10 |
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}} |
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| ATC_suffix = AE01 |
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| Section2 = {{Chembox Properties |
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| ATC_supplemental = {{ATC|D10|AE51}} |
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| C=14|H=10 |O=4 |
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| MolarMass = 242.23 |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| Appearance = 无色固体 |
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| legal_AU_comment = |
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| Density = 1.334 g/cm<sup>3</sup> |
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| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| MeltingPt = 103–105 °C (分解可引起爆炸) |
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| legal_CA_comment = |
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| Solubility = 极微溶于水 |
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| legal_DE = <!-- Anlage I, II, III or Unscheduled--> |
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}} |
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| legal_DE_comment = |
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| Section7 = {{Chembox Hazards |
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| legal_NZ = <!-- Class A, B, C --> |
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| ExternalMSDS = [http://www.ep.net.cn/msds/wuzhi5/52045.htm 过氧化(二)苯甲酰MSDS] |
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| legal_NZ_comment = |
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| EUIndex = 617-008-00-0 |
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| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C --> |
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| EUClass = [[File:Hazard E.svg|70px]] [[File:Hazard X.svg|70px]]<br />爆炸物('''E''') 刺激物('''Xi''') |
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| legal_UK_comment = |
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| RPhrases = {{R3}}, {{R7}}, {{R36}}, {{R43}} |
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| legal_US = OTC |
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| SPhrases = {{S2}}, {{S3/7}}, {{S14}}, {{S36/37/39}} |
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| legal_US_comment = / Rx-only<ref>{{cite web | title=Epsolay- benzoyl peroxide cream | website=DailyMed | date=2022-04-25 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=507e2cd7-6bcf-4606-bc62-694d64537701 | access-date=2022-05-15 | archive-date=2022-05-16 | archive-url=https://web.archive.org/web/20220516045302/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=507e2cd7-6bcf-4606-bc62-694d64537701 | url-status=live }}</ref><ref>{{cite web | title=Epsolay- benzoyl peroxide cream | website=DailyMed | date=2022-05-05 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2bb9bab5-770e-4e91-8d51-b9750454daf8 | access-date=2022-06-19 | archive-date= 2022-06-20 | archive-url=https://web.archive.org/web/20220620010227/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2bb9bab5-770e-4e91-8d51-b9750454daf8 | url-status=live }}</ref> |
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| NFPA-H = 1 |
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| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV--> |
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| NFPA-F = 4 |
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| |
| legal_UN_comment = |
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| legal_status = <!--For countries not listed above--> |
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| NFPA-O = OX |
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| Autoignition = 80 °C |
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<!-- Pharmacokinetic data --> |
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| FlashPt = 125 °C (开杯) |
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| bioavailability = |
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| LD50 = 7710 mg/kg (大鼠经口) |
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| protein_bound = |
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}} |
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| metabolism = |
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| metabolites = |
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| onset = |
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| elimination_half-life = |
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| duration_of_action = |
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| excretion = |
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<!-- Identifiers --> |
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| CAS_number = 94-36-0 |
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| CAS_supplemental = |
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| PubChem = 7187 |
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| IUPHAR_ligand = |
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| DrugBank = DB09096 |
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| ChemSpiderID = 6919 |
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| UNII = W9WZN9A0GM |
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| KEGG = D03093 |
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| KEGG2 = C19346 |
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| ChEBI = 82405 |
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| ChEMBL = 1200370 |
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| NIAID_ChemDB = |
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| synonyms = benzoperoxide、dibenzoyl peroxide (DBPO)及BPO |
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<!-- Chemical and physical data --> |
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| IUPAC_name = benzoic peroxyanhydride<ref>{{BlueBook2013|rec=65.7.5 }}</ref> |
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| C=14 | H=10 | O=4 |
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| SMILES = c1ccc(cc1)C(=O)OOC(=O)c2ccccc2 |
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| StdInChI = 1S/C14H10O4/c15-13(11-7-3-1-4-8-11)17-18-14(16)12-9-5-2-6-10-12/h1-10H |
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| StdInChIKey = OMPJBNCRMGITSC-UHFFFAOYSA-N |
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| density = 1.334 |
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| density_notes = |
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| melting_point = 103 |
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| melting_high = 105 |
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| melting_notes = 分解 |
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| boiling_point = |
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| boiling_notes = |
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| solubility = 不佳 |
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| specific_rotation = |
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<!-- These below are the correct H and P phrases for benzoyl peroxide, but the drug template does not support them. The chembox does. --> |
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<!-- | HPhrases = {{H-phrases|242|317|319|410}} |
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| PPhrases = {{P-phrases|210|235|273|280|370+378|410}} --> |
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}} |
}} |
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''' 過氧化苯甲醯 ''' ({{lang-en|Benzoyl peroxide }})是種[[化合物]](特別是種[[有機過氧化物]]),[[結構式]]為 {{chem2|(C6H5\sC(\dO)O\s)2}},通常縮寫為(BzO)<sub>2</sub>。就結構而言,這分子可描述為透過[[過氧化物]](({{chem2|\sO\sO\s}})連接的兩個[[苯甲醯基]]({{chem2|C6H5\sC(\dO)\s}}, Bz) 。呈白色固體粒狀,有微弱[[苯甲醛]]氣味,難溶於水,但可溶於[[丙酮]]、[[乙醇]]和許多其他有機[[溶劑]]。過氧化苯甲醯是種[[氧化]]劑,主要用於生產聚合物。<ref name=Ullmann/> |
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<!-- Definition and uses --> |
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'''过氧苯甲酰'''(Benzoyl peroxide, '''BPO'''),又称'''过氧化苯甲酰''',是一种[[药物]]与[[化学品]],用来治疗轻至中度[[痤疮]]<ref name=St1998>{{cite book|last1=Stellman|first1=Jeanne Mager|title=Encyclopaedia of Occupational Health and Safety: Guides, indexes, directory|date=1998|publisher=International Labour Organization|isbn=9789221098171|page=104|url=https://books.google.com/books?id=e4_S46UcI2AC&pg=PT404|language=en|deadurl=no|archiveurl=https://web.archive.org/web/20170918185335/https://books.google.com/books?id=e4_S46UcI2AC&pg=PT404|archivedate=2017-09-18|df=}}</ref><ref name=WHO2008/>,在程度严重时也会与其他药物联用。<ref name=WHO2008>{{cite book|title=WHO Model Formulary 2008|date=2009|publisher=World Health Organization|isbn=9789241547659|pages=307–308|url=http://apps.who.int/medicinedocs/documents/s16879e/s16879e.pdf|accessdate=8 January 2017|deadurl=no|archiveurl=https://web.archive.org/web/20161213060118/http://apps.who.int/medicinedocs/documents/s16879e/s16879e.pdf|archivedate=13 December 2016|df=}}</ref><ref name=BNF69>{{cite book|title=British national formulary : BNF 69|url=https://archive.org/details/bnf69britishnati0000unse|date=2015|publisher=British Medical Association|isbn=9780857111562|page=[https://archive.org/details/bnf69britishnati0000unse/page/820 820]|edition=69}}</ref>过氧苯甲酰也可用于面粉漂白、头发漂白、牙齿美白、{{le|纺织品漂白|Textile bleaching}}等。<ref name=Pl2012/><ref name=Pom2012>{{cite book|last1=Pommerville|first1=Glendale Community College Jeffrey C.|last2=Pommerville|first2=Jeffrey|title=Alcamo's Fundamentals of Microbiology: Body Systems|date=2012|publisher=Jones & Bartlett Publishers|isbn=9781449605957|page=214|url=https://books.google.com/books?id=cRaMAQAAQBAJ&pg=PA214|language=en|deadurl=no|archiveurl=https://web.archive.org/web/20170918185335/https://books.google.com/books?id=cRaMAQAAQBAJ&pg=PA214|archivedate=2017-09-18|df=}}</ref><ref>{{cite book|last1=Braun-Falco|first1=Otto|last2=Plewig|first2=Gerd|last3=Wolff|first3=Helmut Heinrich|last4=Burgdorf|first4=Walter|title=Dermatology|date=2012|publisher=Springer Science & Business Media|isbn=9783642979316|page=1039|edition=2|url=https://books.google.com/books?id=kK_rCAAAQBAJ&pg=PA1039|language=en|deadurl=no|archiveurl=https://web.archive.org/web/20170918185335/https://books.google.com/books?id=kK_rCAAAQBAJ&pg=PA1039|archivedate=2017-09-18|df=}}</ref>其也用于塑料工业。<ref name=St1998/> |
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過氧化苯甲醯主要用於生產[[塑膠]]<ref name=Ullmann/<ref name="St1998" />以及漂白[[麵粉]]、{{le|漂白頭髮|hair bleaching|頭髮}}、塑膠和{{le|漂白紡織品|Textile bleaching|紡織品}}。<ref name=Pl2012/><ref name=Pom2012>{{cite book| vauthors = Pommerville JC |title=Alcamo's Fundamentals of Microbiology: Body Systems|date=2012|publisher=Jones & Bartlett Publishers|isbn=978-1-4496-0595-7|page=214|url=https://books.google.com/books?id=cRaMAQAAQBAJ&pg=PA214|language=en|url-status=live|archive-url=https://web.archive.org/web/20170918185335/https://books.google.com/books?id=cRaMAQAAQBAJ&pg=PA214|archive-date=2017-09-18}}</ref> |
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<!-- Side effect and mechanisms --> |
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常见的药物[[副作用]]包括皮肤刺激、干燥和脱皮。[[妊娠]]时使用的安全性尚未明确。过氧苯甲酰为一种[[过氧化物]],為強氧化劑,其通过杀灭致病菌来治疗痤疮。<ref name=WHO2008/><ref name=Ric2015/><ref>{{cite web|title=Benzoyl Peroxide topical Use During Pregnancy {{!}} Drugs.com|url=https://www.drugs.com/pregnancy/benzoyl-peroxide-topical.html|website=www.drugs.com|accessdate=13 January 2017|deadurl=no|archiveurl=https://web.archive.org/web/20170116210235/https://www.drugs.com/pregnancy/benzoyl-peroxide-topical.html|archivedate=16 January 2017|df=}}</ref> <ref name=Pom2012/><ref name=Pl2012/> |
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因其具有漂白劑的功能,而被用來作醫藥和[[水淨化|水消毒]]用途。<ref name=St1998>{{cite book| vauthors = Stellman JM |title=Encyclopaedia of Occupational Health and Safety: Guides, indexes, directory|date=1998|publisher=International Labour Organization|isbn=978-92-2-109817-1|page=104|url=https://books.google.com/books?id=e4_S46UcI2AC&pg=PT404|language=en|url-status=live|archive-url=https://web.archive.org/web/20170918185335/https://books.google.com/books?id=e4_S46UcI2AC&pg=PT404|archive-date=2017-09-18}}</ref><ref name=Pom2012/> |
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<!-- Society and culture --> |
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过氧苯甲酰于1858年被首次制成<ref name=lieb1858>{{cite journal | vauthors = Brodie BC | title = Ueber die Bildung der Hyperoxyde organischer Säureradicale | trans-title = On the Formation of the Peroxides of Organic Acid Radicals | journal = [[Justus Liebigs Ann. Chem.]] | year = 1858 | volume = 108 | pages = 79–83 | doi = 10.1002/jlac.18581080117 | url = https://zenodo.org/record/1427113 | access-date = 2022-06-06 | archive-date = 2020-11-29 | archive-url = https://web.archive.org/web/20201129112907/https://zenodo.org/record/1427113 }}</ref>,并与1930年左右开始被作为药物使用。<ref name=Pl2012>{{cite book|last1=Plewig|first1=G.|last2=Kligman|first2=A. M.|title=ACNE and ROSACEA|date=2012|publisher=Springer Science & Business Media|isbn=9783642597152|page=613|edition=3|url=https://books.google.com/books?id=0cD-CAAAQBAJ&pg=PA613|language=en|deadurl=no|archiveurl=https://web.archive.org/web/20170918185335/https://books.google.com/books?id=0cD-CAAAQBAJ&pg=PA613|archivedate=2017-09-18|df=}}</ref> 该药品被列入[[世界卫生组织基本药物标准清单]], 是医疗系统中最有效安全并且重要的药物之一。<ref name=WHO19th>{{cite web|title=WHO Model List of Essential Medicines (19th List)|url=http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|work=World Health Organization|accessdate=8 December 2016|date=April 2015|deadurl=no|archiveurl=https://web.archive.org/web/20161213052708/http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|archivedate=13 December 2016|df=}}</ref> 该药物为OTC[[非处方药]],<ref name=Ric2015/> 在美国单月疗程的药物费用低于25[[美元]]。<ref name=Ric2015>{{cite book|last1=Hamilton|first1=Richart|title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=173}}</ref> |
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過氧化苯甲醯做藥物使用時,主要是單獨,或是與其他治療方式聯合處理[[痤瘡]]。<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 978-92-4-154765-9 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | pages = 307–308 }}</ref>有些製劑是將過氧化苯甲醯與[[克林黴素]]等[[抗生素]]混合使用。<ref name=BNF69/><ref>{{cite book| vauthors = Braun-Falco O, Plewig G, Wolff HH, Burgdorf W |title=Dermatology|date=2012|publisher=Springer Science & Business Media|isbn=978-3-642-97931-6|page=1039|edition=2|url=https://books.google.com/books?id=kK_rCAAAQBAJ&pg=PA1039|language=en|url-status=live|archive-url=https://web.archive.org/web/20170918185335/https://books.google.com/books?id=kK_rCAAAQBAJ&pg=PA1039|archive-date=2017-09-18}}</ref>它已被列入[[世界衛生組織基本藥物標準清單]]中。<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref>此藥物為一種[[非處方藥]],有[[通用名藥物]]於市面販售。<ref name=Ric2015>{{cite book| vauthors = Hamilton R |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=978-1-284-05756-0|page=173}}</ref><ref name=BNF69>{{cite book|title=British national formulary : BNF 69|date=2015|publisher=British Medical Association|isbn=978-0-85711-156-2|page=820|edition=69}}</ref>有[[牙醫學|牙科]]也使用過氧化苯甲醯作{{le|美白牙齒|teeth whitening}}的用途。 此藥物於2021年是美國最常使用[[處方藥]]中排名第284,開立的處方箋數量超過70萬張。<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=2024-01-14 | archive-date=2024-01-15 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Benzoyl Peroxide - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/BenzoylPeroxide | access-date = 2024-01-14}}</ref> |
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== 性质 == |
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==歷史== |
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白色至微黄色[[斜方晶系|斜方]]结晶或结晶粉末,稍有[[苯甲醛]]气味,有苦杏仁气味。极微溶于水,微溶于[[甲醇]]、[[异丙醇]],稍溶于[[乙醇]],溶于[[乙醚]]、[[丙酮]]、[[氯仿]]、[[苯]]、[[乙酸乙酯]]等。常温下稳定,碱性溶液中或加热时缓慢分解,[[半衰期]]10小时的温度为 72°C,1小时的温度为 90°C,8分钟的温度为 110°C,1分钟的温度为 131°C。<ref>{{cite web en | first = Hui, III | last = Li | title = Synthesis, Characterization and Properties of Vinyl Ester Matrix Resins | url = http://scholar.lib.vt.edu/theses/available/etd-42198-113329/unrestricted/ch2.pdf | series = Ph.D. Dissertation, University of Vermont | volume = Chapter 2 | date = 1998 | deadurl = yes | archiveurl = https://web.archive.org/web/20060920122734/http://scholar.lib.vt.edu/theses/available/etd-42198-113329/unrestricted/ch2.pdf | archivedate = 2006年9月20日 | df = }}.</ref> 干燥状态下受撞击、摩擦或加热可能引发爆炸。加入[[硫酸]]可燃烧。 |
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過氧化苯甲醯由[[德國]]化學家[[尤斯圖斯·馮·李比希]]於1858年首次製成,並撰寫有報告。<ref name=lieb1858/> |
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==結構和反應性== |
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强[[氧化剂]],对皮肤有强烈的刺激和致敏作用,刺激粘膜。贮存时以水为[[稳定剂]],一般含水30%左右;也可以加入[[磷酸钙]]、[[碳酸钙]]、[[硫酸钙]]等不溶性盐类稀释至20%。避免受热与光照,避免与强还原剂、酸、碱、醇类接触。 |
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[[File:Dibenzoyl peroxide (CSD code =DBEZPO01).png|thumb|left| |
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透過[[X射線晶體學]]分析雙過氧化苯甲醯的結構。<ref>{{cite journal |doi=10.1016/0040-4020(82)80157-9|title=Radical pair in crystalline dibenzoyl peroxide evidence for triplet ground states |year=1982 | vauthors = McBride JM, Vary MW |journal=Tetrahedron |volume=38 |issue=6 |pages=765–775 }}</ref>]] |
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李比希最初於1858年將[[過氧化氫]]與[[苯甲醯氯]]反應而完成過氧化苯甲醯的合成,<ref name=lieb1858>{{cite journal | vauthors = Brodie BC | title = Ueber die Bildung der Hyperoxyde organischer Säureradicale | trans-title = On the Formation of the Peroxides of Organic Acid Radicals | journal = [[Justus Liebigs Ann. Chem.]] | year = 1858 | volume = 108 | pages = 79–83 | doi = 10.1002/jlac.18581080117 | url = https://zenodo.org/record/1427113 | access-date = 2019-07-02 | archive-date = 2020-11-29 | archive-url = https://web.archive.org/web/20201129112907/https://zenodo.org/record/1427113 | url-status = live }}</ref>反應可能以下方程式進行: |
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== 制取 == |
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:2 C<sub>6</sub>H<sub>5</sub>C(O)Cl + BaO<sub>2</sub> → (C<sub>6</sub>H<sub>5</sub>CO)<sub>2</sub>O<sub>2</sub> + BaCl<sub>2</sub> |
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用30%[[过氧化氢]]与30%[[氢氧化钠]]溶液反应生成[[过氧化钠]],在0°C以下与[[苯甲酰氯]]反应制得粗品,再经过滤、洗涤、结晶、干燥得到成品。<ref>{{cite book|title=精细化工常用原材料手册|pages=623–624|author=朱洪法主编|publisher=金盾出版社|location=北京|isbn=7-5082-2725-5|date=2003年12月}}</ref> |
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過氧化苯甲醯通常由過氧化氫與苯甲醯氯在[[鹽基]]條件下反應製備。 |
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早期曾用苯甲酰氯与[[过氧化钡]]反应制备过氧化苯甲酰。<ref>{{cite journal en | first = B. C. | last = Brodie | title = Ueber die Bildung der Hyperoxyde organischer Säureradicale | journal = Justus Liebigs Ann. Chem. | year = 1858 | volume = 108 | pages = 79–83 | doi = 10.1002/jlac.18581080117}}.</ref> |
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:2 C<sub>6</sub>H<sub>5</sub>COCl + H<sub>2</sub>O<sub>2</sub> + 2 NaOH → (C<sub>6</sub>H<sub>5</sub>CO)<sub>2</sub>O<sub>2</sub> + 2 NaCl + 2 H<sub>2</sub>O |
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: <math>\rm \ 2 C_6H_5C(O)Cl + BaO_2 \rightarrow [C_6H_5C(O)]_2O_2 + BaCl_2</math> |
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過氧化物中的氧-氧鍵很弱。因此過氧化苯甲醯很容易發生[[均裂]](對稱裂變),形成[[自由基]]: |
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== 用途 == |
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:(C<sub>6</sub>H<sub>5</sub>CO)<sub>2</sub>O<sub>2</sub> → 2 {{chem|C|6|H|5|CO|2|•}} |
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用作[[自由基]][[聚合]]反应的[[自由基引发剂|引发剂]],<ref>Klenk, Herbert; Götz, Peter H.; Siegmeier, Rainer; Mayr, Wilfried (2005), "Peroxy Compounds, Organic", ''Ullmann's Encyclopedia of Industrial Chemistry'', Weinheim: Wiley-VCH, [[doi]]:[http://dx.doi.org/10.1002%2F14356007.a19_199 10.1002/14356007.a19_199].</ref> 其分解反应如下: |
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符號<sup>•</sup>表示其結果是自由基,即含有至少一個不成對的電子。此類物質具有高反應性。均解通常是經加熱引起。過氧化苯甲醯的[[半衰期]]在92°C下為一小時。在131°C時則縮減為一分鐘。<ref>{{cite thesis | vauthors = Li III H | title = Synthesis, Characterization and Properties of Vinyl Ester Matrix Resins | chapter-url = http://hdl.handle.net/10919/30521 | type = Ph.D. | publisher = University of Vermont | chapter = Chapter 2 | year = 1998 | hdl = 10919/30521 | url-status = dead | archive-url = https://web.archive.org/web/20060920122734/http://scholar.lib.vt.edu/theses/available/etd-42198-113329/unrestricted/ch2.pdf | archive-date = 2006-09-20 | access-date = 2007-02-17 }}</ref> |
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: <math>\rm \ [C_6H_5C(O)O]_2 \rightarrow 2C_6H_5C(O)O\cdot </math> |
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科學家於1901年觀察到該化合物會導致{{le|愈創木|Guaiacum officinale}}[[酊劑]]變成藍色,顯示有氧氣釋放。<ref name=kast1901>{{cite journal | vauthors = Kastle JH, Loevenhart AS | date = 1901 | title = On the Nature of Certain Oxidizing Ferments | journal = American Chemical Journal | volume = 2 | pages = 539–566 }}</ref>美國藥學家Arthur Solomon Loevenhart於1905報告其使用過氧化苯甲醯成功治療各種皮膚病,包括[[灼傷]]、慢性[[靜脈曲張]]和{{le|癬菌性鬚部感染|tinea sycosis}}。他在報告中提到於動物實驗中,該化合物的毒性相對較低。<ref name=loev1905>{{cite journal | vauthors = Loevenhart AS | date = 1905 | title = Benzoylsuperoxyds, ein neues therapeutisches Agens | language = German | journal = Therap Monatscheftel | volume = 12 | pages = 426–428 }}</ref><ref name=Pl2012/><ref name=merk2002>{{cite journal | vauthors = Merker PC | title = Benzoyl peroxide: a history of early research and researchers | journal = International Journal of Dermatology | volume = 41 | issue = 3 | pages = 185–8 | date = March 2002 | pmid = 12010349 | doi = 10.1046/j.1365-4362.2002.01371.x | s2cid = 24091844 }}</ref> |
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用作[[乙烯]]、[[丙烯酸]]、[[苯乙烯]]、[[乙酸乙烯酯]]、[[氯乙烯]]等单体的聚合引发剂,[[二甲基硅]]橡胶及凯尔-P-橡胶的[[硫化剂]],[[聚酯]]、[[硅树脂]]及不饱和[[聚酯]]的[[固化剂]],[[面粉]][[增白剂]],快速[[粘合剂]],纤维[[脱色剂]],油脂精炼漂白剂,去除常见[[粉刺]](痤疮),中文药品商品名「班赛」、「本溶塞」乳膏、藥膏等。<ref>{{cite book|title=实用精细化工辞典|pages=278|publisher=轻工业出版社|location=北京|author=安家驹,王伯英编|year=1988|edition=第一版}}</ref> |
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於1929年有使用過氧化苯甲醯治療傷口的建議,1934年有使用過氧化苯甲醯治療{{le|尋常性鬚瘡|sycosis vulgaris}}和{{le|壞死性粟粒性毛囊炎|Acne miliaris necrotica}}的建議。<ref name=merk2002/>然而當時的製劑品質往往會令人產生疑慮。<ref name=Pl2012>{{cite book| vauthors = Plewig G, Kligman AM |title=ACNE and ROSACEA|date=2012|publisher=Springer Science & Business Media |isbn=978-3-642-59715-2 |page=613 |edition=3 |url=https://books.google.com/books?id=0cD-CAAAQBAJ&pg=PA613|language=en|url-status=live|archive-url=https://web.archive.org/web/20170918185335/https://books.google.com/books?id=0cD-CAAAQBAJ&pg=PA613|archive-date=2017-09-18}}</ref>此藥物於1960年在美國正式被核准用於治療痤瘡。<ref name=Pl2012/> |
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== 参见 == |
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===聚合=== |
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* [[偶氮二异丁腈]] |
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過氧化苯甲醯主要被用作[[自由基引發劑]]來引發鍊式聚合反應,<ref name=Ullmann>{{Ullmann | vauthors = Herbert K, Götz PH, Siegmeier R, Mayr W | title = Peroxy Compounds, Organic | doi = 10.1002/14356007.a19_199}}</ref>這些反應常用於製造[[聚酯]]和[[聚甲基丙烯酸甲酯]] (PMMA) 樹脂以及[[牙科用黏合劑]]和[[牙體復形]]劑。<ref name=IARC1999/>過氧化苯甲醯是用於此目的有機過氧化物中最重要的一種,是甚為危險[[過氧化丁酮]]的相對安全替代品。<ref>{{cite web |url= https://polymerdatabase.com/polymer%20chemistry/Diaroyl%20Peroxides.html |website= Polymer Properties Database |title= Initiation By Diacyl Peroxides |access-date= 2018-10-19 |archive-date= 2018-10-19 |archive-url= https://web.archive.org/web/20181019121759/https://polymerdatabase.com/polymer%20chemistry/Diaroyl%20Peroxides.html |url-status= live }}</ref><ref>{{cite web|url=http://www.degaroute.com/sites/dc/Downloadcenter/Evonik/Product/DEGAROUTE/en/Degaroute%20Brosch%C3%BCre.pdf|title=Error - Evonik Industries AG|access-date=2011-04-12|archive-date=2021-08-29|archive-url=https://web.archive.org/web/20210829105907/https://www.degaroute.com/en/degaroute-road-markings|url-status=live}}</ref>過氧化苯甲醯也用於將[[橡膠]][[硫化]],以及作為某些[[醋酸纖維]]紗線的整理劑。<ref name=IARC1999/> |
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* [[二叔丁基过氧化物]] |
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==其他用途== |
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[[Image:Benzoyl peroxide gel.jpg|thumb|right|一含有5%過氧化苯甲醯的水性凝膠軟管,用於治療痤瘡。]] |
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過氧化苯甲醯可有效治療痤瘡,而不會引起抗生素抗藥性。<ref name="Simonart2012">{{cite journal | vauthors = Simonart T | s2cid = 12200694 | title = Newer approaches to the treatment of acne vulgaris | journal = American Journal of Clinical Dermatology | volume = 13 | issue = 6 | pages = 357–64 | date = December 2012 | pmid = 22920095 | doi = 10.2165/11632500-000000000-00000 }}</ref><ref name="Seidler2010"/>它可與[[水楊酸]]、[[硫磺]]、[[紅黴素]]、克林黴素,或是[[阿達帕林]](一種合成[[類視黃醇]])合併使用。兩種常見的複方藥物包括過氧化苯甲醯/克林黴素,和阿達帕林/過氧化苯甲醯,阿達帕林是一種化學上穩定的類視黃醇,可與過氧化苯甲醯<ref>{{cite book | vauthors = Tolaymat L, Dearborn H, Zito PM | chapter = Adapalene |date=2022 | chapter-url=http://www.ncbi.nlm.nih.gov/books/NBK482509/ | title = StatPearls |place=Treasure Island (FL) |publisher=StatPearls Publishing |pmid=29494115 |access-date=2022-07-24 }}</ref>聯合使用。過氧化苯甲醯/克林黴素和過氧化苯甲醯/水楊酸等複方產品似乎比單獨使用過氧化苯甲醯有較佳的治療痤瘡效果。<ref name="Seidler2010">{{cite journal | vauthors = Seidler EM, Kimball AB | title = Meta-analysis comparing efficacy of benzoyl peroxide, clindamycin, benzoyl peroxide with salicylic acid, and combination benzoyl peroxide/clindamycin in acne | journal = Journal of the American Academy of Dermatology | volume = 63 | issue = 1 | pages = 52–62 | date = July 2010 | pmid = 20488582 | doi = 10.1016/j.jaad.2009.07.052 }}</ref>類視黃醇/過氧化苯甲醯組成的複方藥物於2021年在美國獲准用於醫療用途。 |
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用於治療痤瘡的過氧化苯甲醯通常以凝膠、乳膏或液體的形式施用於受影響的區域,濃度從2.5%到5.0%,最高可達10%。<ref name="Simonart2012"/>沒有強而有力的證據支持較高濃度會比較低濃度更為有效。<ref name="Simonart2012"/> |
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===作用機轉=== |
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傳統上過氧化苯甲醯被認為具有三重治療痤瘡的活性 - 它能控油、溶解粉刺,並抑制[[痤瘡丙酸桿菌]](導致痤瘡的主要細菌)生長。<ref name="Simonart2012"/><ref name=":0">{{cite journal | vauthors = Cotterill JA | title = Benzoyl peroxide | journal = Acta Dermato-Venereologica. Supplementum | volume = 89 | pages = 57–63 | date = 1 January 1980 | doi = 10.2340/00015555895763 | pmid = 6162349 | doi-access = free }}</ref>一般來說,尋常性痤瘡是一種[[激素]]介導的[[皮脂腺]]和[[毛囊]][[發炎]]。激素變化導致[[角蛋白]]和皮脂分泌增加,而阻塞毛孔引流。痤瘡丙酸桿菌具有許多分解酶,可分解皮脂中的蛋白質和脂質,引起發炎反應。過氧化苯甲醯的自由基反應可分解此類角蛋白,而暢通皮脂排出(粉刺溶解)。它可引起痤瘡丙酸桿菌的非特異性過氧化,具有殺菌作用,<ref name=Pl2012/>因此被認為可減少皮脂產生,但文獻中對此存有不同看法。<ref name=":0" /><ref name=":1">{{cite journal | vauthors = Worret WI, Fluhr JW | title = [Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid] | language = German | journal = Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology | volume = 4 | issue = 4 | pages = 293–300 | date = April 2006 | pmid = 16638058 | doi = 10.1111/j.1610-0387.2006.05931.x | trans-title = Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid | s2cid = 6924764 }}</ref> |
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一些證據顯示過氧化苯甲醯也具抗發炎作用。在體積微摩爾濃度下,它可防止[[嗜中性球]]釋放活性氧(這是痤瘡發炎反應的過程之一)。<ref name=":1" /> |
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===副作用=== |
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[[File:BenzoperoxideRx.JPG|right|thumb|使用過氧化苯甲醯塗產生的皮膚不適反應。]] |
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將過氧化苯甲醯塗在皮膚上可能會導致發紅、有灼燒感和不適的感覺。這種副作用和使用劑量多寡有關聯。<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 978-92-4-154765-9 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | pages = 307–308 }}</ref><ref name=Ric2015>{{cite book| vauthors = Hamilton R |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=978-1-284-05756-0|page=173}}</ref> |
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由於可能有前述的副作用,建議先從低濃度的製劑開始使用,隨皮膚逐漸產生耐受性後,再升高濃度。通常在連續使用幾週後,皮膚敏感會消失。<ref name=":1" /><ref name="ReferenceA">{{cite book| veditors = Alldredge BK, Koda-Kimble MA, Young LY |title=Applied Therapeutics: The Clinical Use of Drugs|date=2013|publisher=Wolters Kluwer Health/Lippincott Williams & Wilkins|location=Baltimore|isbn=978-1-60913-713-7|page=949|edition=10th}}</ref>避免使用具刺激性潔面乳並在接受陽光照射前塗抹[[防曬乳]]也可降低不適感。<ref name="ReferenceA"/> |
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每五百人中就有一人對過氧化苯甲醯過敏,容易出現灼熱感、發[[癢]]、結痂,甚至可能會有[[水腫]]。大約三分之一使用者在暴露於[[紫外線]]下時會出現[[光毒性]]。<ref>{{cite journal | vauthors = Jeanmougin M, Pedreiro J, Bouchet J, Civatte J | title = [Phototoxic activity of 5% benzoyl peroxide in man. Use of a new methodology] | journal = Dermatologica | volume = 167 | issue = 1 | pages = 19–23 | date = 1983-01-01 | doi = 10.1159/000249739 | pmid = 6628794 }}</ref> |
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===劑量=== |
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在美國,用於治療痤瘡的處方藥和非處方藥製劑中過氧化苯甲醯的典型濃度為2.5%至10%。<ref>{{cite book |last1=Grobel |first1= Hana|last2= Murphy|first2=Sarah A.|date=2018 |title=Chapter 77 - Acne Vulgaris and Acne Rosacea,Integrative Medicine (Fourth Edition) |url= https://www.sciencedirect.com/science/article/abs/pii/B9780323358682000773|location= |publisher= |page=1-2 |isbn= |author-link=|access-date=2024-04-20 }}</ref> |
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===其他醫療用途=== |
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過氧化苯甲醯有在牙科中用作牙齒美白產品的案例。<ref>{{cite web| url =https://worldofdentistry.co.in/some-facts-on-teeth-whitening.php |title =FACTS ON TEETH WHITENING | publisher =World of Dentristry | date = | accessdate = 2024-04-20 }}</ref> |
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==安全性== |
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===爆炸風險=== |
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過氧化苯甲醯與其他有機過氧化物一樣具有潛在爆炸性,<ref>{{cite web| vauthors = Cartwright H |title=Chemical Safety Data: Benzoyl peroxide|url=http://cartwright.chem.ox.ac.uk/hsci/chemicals/benzoyl_peroxide.html|publisher=Oxford University|access-date=2011-08-13|date=2005-03-17|url-status=live|archive-url=https://web.archive.org/web/20101012224750/http://cartwright.chem.ox.ac.uk/hsci/chemicals/benzoyl_peroxide.html|archive-date= 2010-10-12}}</ref>且在無外部引燃的情況下即可起火。純過氧化苯甲醯的危險性較高,因此通常會以溶液或糊狀的形式存在。例如化妝品中僅含有少量過氧化苯甲醯,不具爆炸風險。 |
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===毒性=== |
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過氧化苯甲醯與皮膚接觸後會分解,產生[[苯甲酸]]和氧氣,這兩種物質都無很強的毒性。<ref>{{SIDS-ref | title = Benzoyl peroxide | id = BENZOYLPER | date = April 2004}}</ref> |
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有關過氧化苯甲醯的致癌潛力已被研究過。 一篇發表於1981年《[[科學 (期刊)|科學]]》雜誌上的研究報告提出雖然過氧化苯甲醯不是致癌物,但在{{le|腫瘤起始|Tumor initiation}}時使用,確實會促進癌細胞生長。報告的結論是,"建議謹慎使用過氧化苯甲醯,及其他會產生自由基的化合物"。<ref>{{cite journal | vauthors = Slaga TJ, Klein-Szanto AJ, Triplett LL, Yotti LP, Trosko KE | title = Skin tumor-promoting activity of benzoyl peroxide, a widely used free radical-generating compound | journal = Science | volume = 213 | issue = 4511 | pages = 1023–5 | date = August 1981 | pmid = 6791284 | doi = 10.1126/science.6791284 | bibcode = 1981Sci...213.1023S }}</ref> |
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一份由[[國際癌症研究機構]](IARC)於1999年發表,對致癌性研究的審查提出沒有令人信服的證據表明過氧化苯甲醯痤瘡藥物與人類[[皮膚癌]]有關聯。然而於一些動物研究已發現此種化合物可充當[[致癌物質]],且會增強已知致癌物質的作用。<ref name=IARC1999>International Agency for Research on Cancer (1999): "Benzoyl peroxide". in ''[https://publications.iarc.fr/89 Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide] {{Webarchive|url=https://web.archive.org/web/20200715120252/https://publications.iarc.fr/89 |date=2020-07-15 }}''. Monographs on the Evaluation of Carcinogenic Risks to Humans, number 71, pages 345–358. {{isbn|92-832-1271-1}}</ref> |
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過氧化苯甲醯在溫度高於50°C時會分解成致癌物質 - [[苯]]。<ref>{{cite journal | vauthors = Kucera K, Zenzola N, Hudspeth A, Dubnicka M, Hinz W, Bunick CG, Dabestani A, Light DY | title = Benzoyl Peroxide Drug Products Form Benzene | journal = Environmental Health Perspectives | volume = 132 | issue = 3 | pages = 37702 | date = March 2024 | pmid = 38483533 | doi = 10.1289/EHP13984 | pmc = 10939128 }}</ref><ref>{{Cite web |title=USP Statement on Third Party Laboratory Benzene Findings {{!}} USP |url=https://www.usp.org/news/statement-on-third-party-laboratory-benzene-findings |access-date=2024-03-16 |website=www.usp.org |language=en}}</ref> |
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===刺激皮膚=== |
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於1977年所做的一項人體最大化(HMT)測試,使用5%和10%過氧化苯甲醯含量的配方,有76%的受試者發生接觸致敏反應。<ref>{{cite journal | vauthors = Leyden JJ, Kligman AM | title = Contact sensitization to benzoyl peroxide | journal = Contact Dermatitis | volume = 3 | issue = 5 | pages = 273–5 | date = October 1977 | pmid = 145346 | doi = 10.1111/j.1600-0536.1977.tb03674.x | s2cid = 33553359 }}</ref> |
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[[美國國立職業安全與健康研究所]]制定有職業性接觸過氧化苯甲醯的建議標準。<ref>{{Cite journal |date=2014-06-06 |title=Criteria for a Recommended Standard: Occupational Exposure to Benzoyl Peroxide (77-166) |url=https://www.cdc.gov/niosh/docs/77-166/default.html |url-status=live |doi=10.26616/NIOSHPUB76128 |archive-url=https://web.archive.org/web/20160809050327/http://www.cdc.gov/niosh/docs/1970/77-166.html |archive-date=2016-08-09 |access-date=2016-07-15 |doi-access=free |website=CDC - NIOSH Publications and Products}}</ref> |
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===藥物沾染=== |
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[[File:Benzoyl peroxide stain.jpg|thumb|衣物布料接觸過氧化苯甲醯而發生漂白作用。]] |
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痤瘡藥物接觸衣物或毛髮,如果藥物仍然潮濕時可能會立即導致永久性脫色。即使是間接接觸(例如接觸到用來洗滌含有過氧化苯甲醯衛生用品的毛巾)也會發生漂白作用。<ref>{{cite journal | vauthors = Bojar RA, Cunliffe WJ, Holland KT | title = The short-term treatment of acne vulgaris with benzoyl peroxide: effects on the surface and follicular cutaneous microflora | journal = The British Journal of Dermatology | volume = 132 | issue = 2 | pages = 204–8 | date = February 1995 | pmid = 7888356 | doi = 10.1111/j.1365-2133.1995.tb05014.x | s2cid = 22468429 }}</ref> |
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== 參考文獻 == |
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{{Reflist|2}} |
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== 外部連結 == |
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*{{ICSC|0225|02}} |
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*{{PGCH|0052}} |
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*{{SIDS | title = Benzoyl peroxide | id = BENZOYLPER}} |
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*[https://www.americanchemistry.com/industry-groups/organic-peroxide-producers-safety-division-oppsd Organic Peroxide Producers Safety Division (OPPSD)] |
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{{E number infobox 920-929}} |
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{{模板:抗痤瘡製劑}} |
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{{Portal bar | Medicine}} |
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{{Authority control}} |
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{{DEFAULTSORT:Benzoyl Peroxide}} |
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{{draft categories| |
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[[分類:抗痤瘡製劑]] |
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[[分類:苯衍生物]] |
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[[分類:IARC第3類致癌物質]] |
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[[分類:有機過氧化物]] |
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[[分類:自由基引發劑]] |
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[[分類:世界衛生組織基本藥物]] |
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[[分類:RTT]] |
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}} |
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== 参考资料 == |
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{{reflist}} |
{{reflist}} |
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{{Infobox drug |
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| image = Benzoyl-peroxide.svg |
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| width = |
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| alt = |
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| image2 = Benzoyl-peroxide-from-xtal-3D-bs-17.png |
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| width2 = |
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| alt2 = |
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| caption = [[鍵線式|骨架式]] (上圖) [[球棍模型]] (下圖) |
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<!-- Clinical data --> |
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| pronounce = |
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| tradename = Benzac、Panoxyl及其他 |
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| Drugs.com = {{Drugs.com|ppa|benzoyl-peroxide}} |
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| MedlinePlus = a601026 |
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| DailyMedID = Benzoyl peroxide |
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| pregnancy_AU = <!-- A/B1/B2/B3/C/D/X --> |
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| pregnancy_AU_comment = |
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| pregnancy_category= |
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| routes_of_administration = [[外用藥物]] |
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| class = |
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| ATC_prefix = D10 |
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| ATC_suffix = AE01 |
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| ATC_supplemental = {{ATC|D10|AE51}} |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_AU_comment = |
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| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_CA_comment = |
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| legal_DE = <!-- Anlage I, II, III or Unscheduled--> |
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| legal_DE_comment = |
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| legal_NZ = <!-- Class A, B, C --> |
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| legal_NZ_comment = |
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| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C --> |
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| legal_UK_comment = |
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| legal_US = OTC |
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| legal_US_comment = / Rx-only<ref>{{cite web | title=Epsolay- benzoyl peroxide cream | website=DailyMed | date=2022-04-25 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=507e2cd7-6bcf-4606-bc62-694d64537701 | access-date=2022-05-15 | archive-date=2022-05-16 | archive-url=https://web.archive.org/web/20220516045302/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=507e2cd7-6bcf-4606-bc62-694d64537701 | url-status=live }}</ref><ref>{{cite web | title=Epsolay- benzoyl peroxide cream | website=DailyMed | date=2022-05-05 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2bb9bab5-770e-4e91-8d51-b9750454daf8 | access-date=2022-06-19 | archive-date= 2022-06-20 | archive-url=https://web.archive.org/web/20220620010227/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2bb9bab5-770e-4e91-8d51-b9750454daf8 | url-status=live }}</ref> |
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| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV--> |
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| legal_UN_comment = |
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| legal_status = <!--For countries not listed above--> |
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<!-- Pharmacokinetic data --> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| metabolites = |
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| onset = |
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| elimination_half-life = |
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| duration_of_action = |
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| excretion = |
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<!-- Identifiers --> |
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| CAS_number = 94-36-0 |
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| CAS_supplemental = |
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| PubChem = 7187 |
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| IUPHAR_ligand = |
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| DrugBank = DB09096 |
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| ChemSpiderID = 6919 |
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| UNII = W9WZN9A0GM |
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| KEGG = D03093 |
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| KEGG2 = C19346 |
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| ChEBI = 82405 |
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| ChEMBL = 1200370 |
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| NIAID_ChemDB = |
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| synonyms = benzoperoxide、dibenzoyl peroxide (DBPO)及BPO |
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<!-- Chemical and physical data --> |
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| IUPAC_name = benzoic peroxyanhydride<ref>{{BlueBook2013|rec=65.7.5 }}</ref> |
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| C=14 | H=10 | O=4 |
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| SMILES = c1ccc(cc1)C(=O)OOC(=O)c2ccccc2 |
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| StdInChI = 1S/C14H10O4/c15-13(11-7-3-1-4-8-11)17-18-14(16)12-9-5-2-6-10-12/h1-10H |
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| StdInChIKey = OMPJBNCRMGITSC-UHFFFAOYSA-N |
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| density = 1.334 |
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| density_notes = |
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| melting_point = 103 |
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| melting_high = 105 |
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| melting_notes = 分解 |
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| boiling_point = |
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| boiling_notes = |
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| solubility = 不佳 |
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| specific_rotation = |
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<!-- These below are the correct H and P phrases for benzoyl peroxide, but the drug template does not support them. The chembox does. --> |
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<!-- | HPhrases = {{H-phrases|242|317|319|410}} |
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| PPhrases = {{P-phrases|210|235|273|280|370+378|410}} --> |
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}} |
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''' 過氧化苯甲醯 ''' ({{lang-en|Benzoyl peroxide }})是種[[化合物]](特別是種[[有機過氧化物]]),[[結構式]]為 {{chem2|(C6H5\sC(\dO)O\s)2}},通常縮寫為(BzO)<sub>2</sub>。就結構而言,這分子可描述為透過[[過氧化物]](({{chem2|\sO\sO\s}})連接的兩個[[苯甲醯基]]({{chem2|C6H5\sC(\dO)\s}}, Bz) 。呈白色固體粒狀,有微弱[[苯甲醛]]氣味,難溶於水,但可溶於[[丙酮]]、[[乙醇]]和許多其他有機[[溶劑]]。過氧化苯甲醯是種[[氧化]]劑,主要用於生產聚合物。<ref name=Ullmann/> |
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過氧化苯甲醯主要用於生產[[塑膠]]<ref name=Ullmann/<ref name="St1998" />以及漂白[[麵粉]]、{{le|漂白頭髮|hair bleaching|頭髮}}、塑膠和{{le|漂白紡織品|Textile bleaching|紡織品}}。<ref name=Pl2012/><ref name=Pom2012>{{cite book| vauthors = Pommerville JC |title=Alcamo's Fundamentals of Microbiology: Body Systems|date=2012|publisher=Jones & Bartlett Publishers|isbn=978-1-4496-0595-7|page=214|url=https://books.google.com/books?id=cRaMAQAAQBAJ&pg=PA214|language=en|url-status=live|archive-url=https://web.archive.org/web/20170918185335/https://books.google.com/books?id=cRaMAQAAQBAJ&pg=PA214|archive-date=2017-09-18}}</ref> |
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因其具有漂白劑的功能,而被用來作醫藥和[[水淨化|水消毒]]用途。<ref name=St1998>{{cite book| vauthors = Stellman JM |title=Encyclopaedia of Occupational Health and Safety: Guides, indexes, directory|date=1998|publisher=International Labour Organization|isbn=978-92-2-109817-1|page=104|url=https://books.google.com/books?id=e4_S46UcI2AC&pg=PT404|language=en|url-status=live|archive-url=https://web.archive.org/web/20170918185335/https://books.google.com/books?id=e4_S46UcI2AC&pg=PT404|archive-date=2017-09-18}}</ref><ref name=Pom2012/> |
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過氧化苯甲醯做藥物使用時,主要是單獨,或是與其他治療方式聯合處理[[痤瘡]]。<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 978-92-4-154765-9 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | pages = 307–308 }}</ref>有些製劑是將過氧化苯甲醯與[[克林黴素]]等[[抗生素]]混合使用。<ref name=BNF69/><ref>{{cite book| vauthors = Braun-Falco O, Plewig G, Wolff HH, Burgdorf W |title=Dermatology|date=2012|publisher=Springer Science & Business Media|isbn=978-3-642-97931-6|page=1039|edition=2|url=https://books.google.com/books?id=kK_rCAAAQBAJ&pg=PA1039|language=en|url-status=live|archive-url=https://web.archive.org/web/20170918185335/https://books.google.com/books?id=kK_rCAAAQBAJ&pg=PA1039|archive-date=2017-09-18}}</ref>它已被列入[[世界衛生組織基本藥物標準清單]]中。<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref>此藥物為一種[[非處方藥]],有[[通用名藥物]]於市面販售。<ref name=Ric2015>{{cite book| vauthors = Hamilton R |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=978-1-284-05756-0|page=173}}</ref><ref name=BNF69>{{cite book|title=British national formulary : BNF 69|date=2015|publisher=British Medical Association|isbn=978-0-85711-156-2|page=820|edition=69}}</ref>有[[牙醫學|牙科]]也使用過氧化苯甲醯作{{le|美白牙齒|teeth whitening}}的用途。 此藥物於2021年是美國最常使用[[處方藥]]中排名第284,開立的處方箋數量超過70萬張。<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=2024-01-14 | archive-date=2024-01-15 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Benzoyl Peroxide - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/BenzoylPeroxide | access-date = 2024-01-14}}</ref> |
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==歷史== |
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過氧化苯甲醯由[[德國]]化學家[[尤斯圖斯·馮·李比希]]於1858年首次製成,並撰寫有報告。<ref name=lieb1858/> |
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==結構和反應性== |
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[[File:Dibenzoyl peroxide (CSD code =DBEZPO01).png|thumb|left| |
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透過[[X射線晶體學]]分析雙過氧化苯甲醯的結構。<ref>{{cite journal |doi=10.1016/0040-4020(82)80157-9|title=Radical pair in crystalline dibenzoyl peroxide evidence for triplet ground states |year=1982 | vauthors = McBride JM, Vary MW |journal=Tetrahedron |volume=38 |issue=6 |pages=765–775 }}</ref>]] |
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李比希最初於1858年將[[過氧化氫]]與[[苯甲醯氯]]反應而完成過氧化苯甲醯的合成,<ref name=lieb1858>{{cite journal | vauthors = Brodie BC | title = Ueber die Bildung der Hyperoxyde organischer Säureradicale | trans-title = On the Formation of the Peroxides of Organic Acid Radicals | journal = [[Justus Liebigs Ann. Chem.]] | year = 1858 | volume = 108 | pages = 79–83 | doi = 10.1002/jlac.18581080117 | url = https://zenodo.org/record/1427113 | access-date = 2019-07-02 | archive-date = 2020-11-29 | archive-url = https://web.archive.org/web/20201129112907/https://zenodo.org/record/1427113 | url-status = live }}</ref>反應可能以下方程式進行: |
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:2 C<sub>6</sub>H<sub>5</sub>C(O)Cl + BaO<sub>2</sub> → (C<sub>6</sub>H<sub>5</sub>CO)<sub>2</sub>O<sub>2</sub> + BaCl<sub>2</sub> |
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過氧化苯甲醯通常由過氧化氫與苯甲醯氯在[[鹽基]]條件下反應製備。 |
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:2 C<sub>6</sub>H<sub>5</sub>COCl + H<sub>2</sub>O<sub>2</sub> + 2 NaOH → (C<sub>6</sub>H<sub>5</sub>CO)<sub>2</sub>O<sub>2</sub> + 2 NaCl + 2 H<sub>2</sub>O |
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過氧化物中的氧-氧鍵很弱。因此過氧化苯甲醯很容易發生[[均裂]](對稱裂變),形成[[自由基]]: |
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:(C<sub>6</sub>H<sub>5</sub>CO)<sub>2</sub>O<sub>2</sub> → 2 {{chem|C|6|H|5|CO|2|•}} |
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符號<sup>•</sup>表示其結果是自由基,即含有至少一個不成對的電子。此類物質具有高反應性。均解通常是經加熱引起。過氧化苯甲醯的[[半衰期]]在92°C下為一小時。在131°C時則縮減為一分鐘。<ref>{{cite thesis | vauthors = Li III H | title = Synthesis, Characterization and Properties of Vinyl Ester Matrix Resins | chapter-url = http://hdl.handle.net/10919/30521 | type = Ph.D. | publisher = University of Vermont | chapter = Chapter 2 | year = 1998 | hdl = 10919/30521 | url-status = dead | archive-url = https://web.archive.org/web/20060920122734/http://scholar.lib.vt.edu/theses/available/etd-42198-113329/unrestricted/ch2.pdf | archive-date = 2006-09-20 | access-date = 2007-02-17 }}</ref> |
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科學家於1901年觀察到該化合物會導致{{le|愈創木|Guaiacum officinale}}[[酊劑]]變成藍色,顯示有氧氣釋放。<ref name=kast1901>{{cite journal | vauthors = Kastle JH, Loevenhart AS | date = 1901 | title = On the Nature of Certain Oxidizing Ferments | journal = American Chemical Journal | volume = 2 | pages = 539–566 }}</ref>美國藥學家Arthur Solomon Loevenhart於1905報告其使用過氧化苯甲醯成功治療各種皮膚病,包括[[灼傷]]、慢性[[靜脈曲張]]和{{le|癬菌性鬚部感染|tinea sycosis}}。他在報告中提到於動物實驗中,該化合物的毒性相對較低。<ref name=loev1905>{{cite journal | vauthors = Loevenhart AS | date = 1905 | title = Benzoylsuperoxyds, ein neues therapeutisches Agens | language = German | journal = Therap Monatscheftel | volume = 12 | pages = 426–428 }}</ref><ref name=Pl2012/><ref name=merk2002>{{cite journal | vauthors = Merker PC | title = Benzoyl peroxide: a history of early research and researchers | journal = International Journal of Dermatology | volume = 41 | issue = 3 | pages = 185–8 | date = March 2002 | pmid = 12010349 | doi = 10.1046/j.1365-4362.2002.01371.x | s2cid = 24091844 }}</ref> |
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於1929年有使用過氧化苯甲醯治療傷口的建議,1934年有使用過氧化苯甲醯治療{{le|尋常性鬚瘡|sycosis vulgaris}}和{{le|壞死性粟粒性毛囊炎|Acne miliaris necrotica}}的建議。<ref name=merk2002/>然而當時的製劑品質往往會令人產生疑慮。<ref name=Pl2012>{{cite book| vauthors = Plewig G, Kligman AM |title=ACNE and ROSACEA|date=2012|publisher=Springer Science & Business Media |isbn=978-3-642-59715-2 |page=613 |edition=3 |url=https://books.google.com/books?id=0cD-CAAAQBAJ&pg=PA613|language=en|url-status=live|archive-url=https://web.archive.org/web/20170918185335/https://books.google.com/books?id=0cD-CAAAQBAJ&pg=PA613|archive-date=2017-09-18}}</ref>此藥物於1960年在美國正式被核准用於治療痤瘡。<ref name=Pl2012/> |
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===聚合=== |
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過氧化苯甲醯主要被用作[[自由基引發劑]]來引發鍊式聚合反應,<ref name=Ullmann>{{Ullmann | vauthors = Herbert K, Götz PH, Siegmeier R, Mayr W | title = Peroxy Compounds, Organic | doi = 10.1002/14356007.a19_199}}</ref>這些反應常用於製造[[聚酯]]和[[聚甲基丙烯酸甲酯]] (PMMA) 樹脂以及[[牙科用黏合劑]]和[[牙體復形]]劑。<ref name=IARC1999/>過氧化苯甲醯是用於此目的有機過氧化物中最重要的一種,是甚為危險[[過氧化丁酮]]的相對安全替代品。<ref>{{cite web |url= https://polymerdatabase.com/polymer%20chemistry/Diaroyl%20Peroxides.html |website= Polymer Properties Database |title= Initiation By Diacyl Peroxides |access-date= 2018-10-19 |archive-date= 2018-10-19 |archive-url= https://web.archive.org/web/20181019121759/https://polymerdatabase.com/polymer%20chemistry/Diaroyl%20Peroxides.html |url-status= live }}</ref><ref>{{cite web|url=http://www.degaroute.com/sites/dc/Downloadcenter/Evonik/Product/DEGAROUTE/en/Degaroute%20Brosch%C3%BCre.pdf|title=Error - Evonik Industries AG|access-date=2011-04-12|archive-date=2021-08-29|archive-url=https://web.archive.org/web/20210829105907/https://www.degaroute.com/en/degaroute-road-markings|url-status=live}}</ref>過氧化苯甲醯也用於將[[橡膠]][[硫化]],以及作為某些[[醋酸纖維]]紗線的整理劑。<ref name=IARC1999/> |
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==其他用途== |
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[[Image:Benzoyl peroxide gel.jpg|thumb|right|一含有5%過氧化苯甲醯的水性凝膠軟管,用於治療痤瘡。]] |
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過氧化苯甲醯可有效治療痤瘡,而不會引起抗生素抗藥性。<ref name="Simonart2012">{{cite journal | vauthors = Simonart T | s2cid = 12200694 | title = Newer approaches to the treatment of acne vulgaris | journal = American Journal of Clinical Dermatology | volume = 13 | issue = 6 | pages = 357–64 | date = December 2012 | pmid = 22920095 | doi = 10.2165/11632500-000000000-00000 }}</ref><ref name="Seidler2010"/>它可與[[水楊酸]]、[[硫磺]]、[[紅黴素]]、克林黴素,或是[[阿達帕林]](一種合成[[類視黃醇]])合併使用。兩種常見的複方藥物包括過氧化苯甲醯/克林黴素,和阿達帕林/過氧化苯甲醯,阿達帕林是一種化學上穩定的類視黃醇,可與過氧化苯甲醯<ref>{{cite book | vauthors = Tolaymat L, Dearborn H, Zito PM | chapter = Adapalene |date=2022 | chapter-url=http://www.ncbi.nlm.nih.gov/books/NBK482509/ | title = StatPearls |place=Treasure Island (FL) |publisher=StatPearls Publishing |pmid=29494115 |access-date=2022-07-24 }}</ref>聯合使用。過氧化苯甲醯/克林黴素和過氧化苯甲醯/水楊酸等複方產品似乎比單獨使用過氧化苯甲醯有較佳的治療痤瘡效果。<ref name="Seidler2010">{{cite journal | vauthors = Seidler EM, Kimball AB | title = Meta-analysis comparing efficacy of benzoyl peroxide, clindamycin, benzoyl peroxide with salicylic acid, and combination benzoyl peroxide/clindamycin in acne | journal = Journal of the American Academy of Dermatology | volume = 63 | issue = 1 | pages = 52–62 | date = July 2010 | pmid = 20488582 | doi = 10.1016/j.jaad.2009.07.052 }}</ref>類視黃醇/過氧化苯甲醯組成的複方藥物於2021年在美國獲准用於醫療用途。 |
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用於治療痤瘡的過氧化苯甲醯通常以凝膠、乳膏或液體的形式施用於受影響的區域,濃度從2.5%到5.0%,最高可達10%。<ref name="Simonart2012"/>沒有強而有力的證據支持較高濃度會比較低濃度更為有效。<ref name="Simonart2012"/> |
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===作用機轉=== |
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傳統上過氧化苯甲醯被認為具有三重治療痤瘡的活性 - 它能控油、溶解粉刺,並抑制[[痤瘡丙酸桿菌]](導致痤瘡的主要細菌)生長。<ref name="Simonart2012"/><ref name=":0">{{cite journal | vauthors = Cotterill JA | title = Benzoyl peroxide | journal = Acta Dermato-Venereologica. Supplementum | volume = 89 | pages = 57–63 | date = 1 January 1980 | doi = 10.2340/00015555895763 | pmid = 6162349 | doi-access = free }}</ref>一般來說,尋常性痤瘡是一種[[激素]]介導的[[皮脂腺]]和[[毛囊]][[發炎]]。激素變化導致[[角蛋白]]和皮脂分泌增加,而阻塞毛孔引流。痤瘡丙酸桿菌具有許多分解酶,可分解皮脂中的蛋白質和脂質,引起發炎反應。過氧化苯甲醯的自由基反應可分解此類角蛋白,而暢通皮脂排出(粉刺溶解)。它可引起痤瘡丙酸桿菌的非特異性過氧化,具有殺菌作用,<ref name=Pl2012/>因此被認為可減少皮脂產生,但文獻中對此存有不同看法。<ref name=":0" /><ref name=":1">{{cite journal | vauthors = Worret WI, Fluhr JW | title = [Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid] | language = German | journal = Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology | volume = 4 | issue = 4 | pages = 293–300 | date = April 2006 | pmid = 16638058 | doi = 10.1111/j.1610-0387.2006.05931.x | trans-title = Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid | s2cid = 6924764 }}</ref> |
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一些證據顯示過氧化苯甲醯也具抗發炎作用。在體積微摩爾濃度下,它可防止[[嗜中性球]]釋放活性氧(這是痤瘡發炎反應的過程之一)。<ref name=":1" /> |
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===副作用=== |
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[[File:BenzoperoxideRx.JPG|right|thumb|使用過氧化苯甲醯塗產生的皮膚不適反應。]] |
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將過氧化苯甲醯塗在皮膚上可能會導致發紅、有灼燒感和不適的感覺。這種副作用和使用劑量多寡有關聯。<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 978-92-4-154765-9 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | pages = 307–308 }}</ref><ref name=Ric2015>{{cite book| vauthors = Hamilton R |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=978-1-284-05756-0|page=173}}</ref> |
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由於可能有前述的副作用,建議先從低濃度的製劑開始使用,隨皮膚逐漸產生耐受性後,再升高濃度。通常在連續使用幾週後,皮膚敏感會消失。<ref name=":1" /><ref name="ReferenceA">{{cite book| veditors = Alldredge BK, Koda-Kimble MA, Young LY |title=Applied Therapeutics: The Clinical Use of Drugs|date=2013|publisher=Wolters Kluwer Health/Lippincott Williams & Wilkins|location=Baltimore|isbn=978-1-60913-713-7|page=949|edition=10th}}</ref>避免使用具刺激性潔面乳並在接受陽光照射前塗抹[[防曬乳]]也可降低不適感。<ref name="ReferenceA"/> |
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每五百人中就有一人對過氧化苯甲醯過敏,容易出現灼熱感、發[[癢]]、結痂,甚至可能會有[[水腫]]。大約三分之一使用者在暴露於[[紫外線]]下時會出現[[光毒性]]。<ref>{{cite journal | vauthors = Jeanmougin M, Pedreiro J, Bouchet J, Civatte J | title = [Phototoxic activity of 5% benzoyl peroxide in man. Use of a new methodology] | journal = Dermatologica | volume = 167 | issue = 1 | pages = 19–23 | date = 1983-01-01 | doi = 10.1159/000249739 | pmid = 6628794 }}</ref> |
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===劑量=== |
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在美國,用於治療痤瘡的處方藥和非處方藥製劑中過氧化苯甲醯的典型濃度為2.5%至10%。<ref>{{cite book |last1=Grobel |first1= Hana|last2= Murphy|first2=Sarah A.|date=2018 |title=Chapter 77 - Acne Vulgaris and Acne Rosacea,Integrative Medicine (Fourth Edition) |url= https://www.sciencedirect.com/science/article/abs/pii/B9780323358682000773|location= |publisher= |page=1-2 |isbn= |author-link=|access-date=2024-04-20 }}</ref> |
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===其他醫療用途=== |
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過氧化苯甲醯有在牙科中用作牙齒美白產品的案例。<ref>{{cite web| url =https://worldofdentistry.co.in/some-facts-on-teeth-whitening.php |title =FACTS ON TEETH WHITENING | publisher =World of Dentristry | date = | accessdate = 2024-04-20 }}</ref> |
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==安全性== |
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===爆炸風險=== |
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過氧化苯甲醯與其他有機過氧化物一樣具有潛在爆炸性,<ref>{{cite web| vauthors = Cartwright H |title=Chemical Safety Data: Benzoyl peroxide|url=http://cartwright.chem.ox.ac.uk/hsci/chemicals/benzoyl_peroxide.html|publisher=Oxford University|access-date=2011-08-13|date=2005-03-17|url-status=live|archive-url=https://web.archive.org/web/20101012224750/http://cartwright.chem.ox.ac.uk/hsci/chemicals/benzoyl_peroxide.html|archive-date= 2010-10-12}}</ref>且在無外部引燃的情況下即可起火。純過氧化苯甲醯的危險性較高,因此通常會以溶液或糊狀的形式存在。例如化妝品中僅含有少量過氧化苯甲醯,不具爆炸風險。 |
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===毒性=== |
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過氧化苯甲醯與皮膚接觸後會分解,產生[[苯甲酸]]和氧氣,這兩種物質都無很強的毒性。<ref>{{SIDS-ref | title = Benzoyl peroxide | id = BENZOYLPER | date = April 2004}}</ref> |
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有關過氧化苯甲醯的致癌潛力已被研究過。 一篇發表於1981年《[[科學 (期刊)|科學]]》雜誌上的研究報告提出雖然過氧化苯甲醯不是致癌物,但在{{le|腫瘤起始|Tumor initiation}}時使用,確實會促進癌細胞生長。報告的結論是,"建議謹慎使用過氧化苯甲醯,及其他會產生自由基的化合物"。<ref>{{cite journal | vauthors = Slaga TJ, Klein-Szanto AJ, Triplett LL, Yotti LP, Trosko KE | title = Skin tumor-promoting activity of benzoyl peroxide, a widely used free radical-generating compound | journal = Science | volume = 213 | issue = 4511 | pages = 1023–5 | date = August 1981 | pmid = 6791284 | doi = 10.1126/science.6791284 | bibcode = 1981Sci...213.1023S }}</ref> |
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一份由[[國際癌症研究機構]](IARC)於1999年發表,對致癌性研究的審查提出沒有令人信服的證據表明過氧化苯甲醯痤瘡藥物與人類[[皮膚癌]]有關聯。然而於一些動物研究已發現此種化合物可充當[[致癌物質]],且會增強已知致癌物質的作用。<ref name=IARC1999>International Agency for Research on Cancer (1999): "Benzoyl peroxide". in ''[https://publications.iarc.fr/89 Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide] {{Webarchive|url=https://web.archive.org/web/20200715120252/https://publications.iarc.fr/89 |date=2020-07-15 }}''. Monographs on the Evaluation of Carcinogenic Risks to Humans, number 71, pages 345–358. {{isbn|92-832-1271-1}}</ref> |
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過氧化苯甲醯在溫度高於50°C時會分解成致癌物質 - [[苯]]。<ref>{{cite journal | vauthors = Kucera K, Zenzola N, Hudspeth A, Dubnicka M, Hinz W, Bunick CG, Dabestani A, Light DY | title = Benzoyl Peroxide Drug Products Form Benzene | journal = Environmental Health Perspectives | volume = 132 | issue = 3 | pages = 37702 | date = March 2024 | pmid = 38483533 | doi = 10.1289/EHP13984 | pmc = 10939128 }}</ref><ref>{{Cite web |title=USP Statement on Third Party Laboratory Benzene Findings {{!}} USP |url=https://www.usp.org/news/statement-on-third-party-laboratory-benzene-findings |access-date=2024-03-16 |website=www.usp.org |language=en}}</ref> |
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===刺激皮膚=== |
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於1977年所做的一項人體最大化(HMT)測試,使用5%和10%過氧化苯甲醯含量的配方,有76%的受試者發生接觸致敏反應。<ref>{{cite journal | vauthors = Leyden JJ, Kligman AM | title = Contact sensitization to benzoyl peroxide | journal = Contact Dermatitis | volume = 3 | issue = 5 | pages = 273–5 | date = October 1977 | pmid = 145346 | doi = 10.1111/j.1600-0536.1977.tb03674.x | s2cid = 33553359 }}</ref> |
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[[美國國立職業安全與健康研究所]]制定有職業性接觸過氧化苯甲醯的建議標準。<ref>{{Cite journal |date=2014-06-06 |title=Criteria for a Recommended Standard: Occupational Exposure to Benzoyl Peroxide (77-166) |url=https://www.cdc.gov/niosh/docs/77-166/default.html |url-status=live |doi=10.26616/NIOSHPUB76128 |archive-url=https://web.archive.org/web/20160809050327/http://www.cdc.gov/niosh/docs/1970/77-166.html |archive-date=2016-08-09 |access-date=2016-07-15 |doi-access=free |website=CDC - NIOSH Publications and Products}}</ref> |
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===藥物沾染=== |
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[[File:Benzoyl peroxide stain.jpg|thumb|衣物布料接觸過氧化苯甲醯而發生漂白作用。]] |
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痤瘡藥物接觸衣物或毛髮,如果藥物仍然潮濕時可能會立即導致永久性脫色。即使是間接接觸(例如接觸到用來洗滌含有過氧化苯甲醯衛生用品的毛巾)也會發生漂白作用。<ref>{{cite journal | vauthors = Bojar RA, Cunliffe WJ, Holland KT | title = The short-term treatment of acne vulgaris with benzoyl peroxide: effects on the surface and follicular cutaneous microflora | journal = The British Journal of Dermatology | volume = 132 | issue = 2 | pages = 204–8 | date = February 1995 | pmid = 7888356 | doi = 10.1111/j.1365-2133.1995.tb05014.x | s2cid = 22468429 }}</ref> |
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== 參考文獻 == |
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{{Reflist|2}} |
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== 外部連結 == |
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*{{ICSC|0225|02}} |
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*{{PGCH|0052}} |
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*{{SIDS | title = Benzoyl peroxide | id = BENZOYLPER}} |
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*[https://www.americanchemistry.com/industry-groups/organic-peroxide-producers-safety-division-oppsd Organic Peroxide Producers Safety Division (OPPSD)] |
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{{E number infobox 920-929}} |
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{{苯}} |
{{苯}} |
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{{抗痤 |
{{模板:抗痤瘡製劑}} |
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{{Portal bar | Medicine}} |
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{{Authority control}} |
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{{DEFAULTSORT:Benzoyl Peroxide}} |
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[[Category:抗痤疮制剂]] |
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[[分類:抗痤瘡製劑]] |
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[[Category:IARC第3类致癌物质]] |
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[[ |
[[分類:苯衍生物]] |
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[[分類:IARC第3類致癌物質]] |
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[[Category:自由基引发剂]] |
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[[ |
[[分類:有機過氧化物]] |
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[[分類:自由基引發劑]] |
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[[Category:1850年代发现的物质]] |
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[[分類:世界衛生組織基本藥物]] |
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[[分類:RTT]] |
2024年4月26日 (五) 12:55的版本
臨床資料 | |
---|---|
商品名 | Benzac、Panoxyl及其他 |
其他名稱 | benzoperoxide、dibenzoyl peroxide (DBPO)及BPO |
AHFS/Drugs.com | 专业药物信息 |
MedlinePlus | a601026 |
核准狀況 | |
给药途径 | 外用藥物 |
ATC碼 | |
法律規範狀態 | |
法律規範 | |
识别信息 | |
CAS号 | 94-36-0 |
PubChem CID | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.002.116 |
化学信息 | |
化学式 | C14H10O4 |
摩尔质量 | 242.23 g·mol−1 |
3D模型(JSmol) | |
密度 | 1.334 g/cm3 |
熔点 | 103至105 °C(217至221 °F) 分解 |
水溶性 | 不佳 mg/mL (20 °C) |
| |
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過氧化苯甲醯 (英語:Benzoyl peroxide)是種化合物(特別是種有機過氧化物),結構式為 (C
6H
5–C(=O)O–)
2,通常縮寫為(BzO)2。就結構而言,這分子可描述為透過過氧化物((–O–O–)連接的兩個苯甲醯基(C
6H
5–C(=O)–, Bz) 。呈白色固體粒狀,有微弱苯甲醛氣味,難溶於水,但可溶於丙酮、乙醇和許多其他有機溶劑。過氧化苯甲醯是種氧化劑,主要用於生產聚合物。[4]
過氧化苯甲醯主要用於生產塑膠[5]以及漂白麵粉、頭髮、塑膠和紡織品。[6][7]
因其具有漂白劑的功能,而被用來作醫藥和水消毒用途。[5][7]
過氧化苯甲醯做藥物使用時,主要是單獨,或是與其他治療方式聯合處理痤瘡。[8]有些製劑是將過氧化苯甲醯與克林黴素等抗生素混合使用。[9][10]它已被列入世界衛生組織基本藥物標準清單中。[11]此藥物為一種非處方藥,有通用名藥物於市面販售。[12][9]有牙科也使用過氧化苯甲醯作美白牙齒的用途。 此藥物於2021年是美國最常使用處方藥中排名第284,開立的處方箋數量超過70萬張。[13][14]
歷史
過氧化苯甲醯由德國化學家尤斯圖斯·馮·李比希於1858年首次製成,並撰寫有報告。[15]
結構和反應性
李比希最初於1858年將過氧化氫與苯甲醯氯反應而完成過氧化苯甲醯的合成,[15]反應可能以下方程式進行:
- 2 C6H5C(O)Cl + BaO2 → (C6H5CO)2O2 + BaCl2
過氧化苯甲醯通常由過氧化氫與苯甲醯氯在鹽基條件下反應製備。
- 2 C6H5COCl + H2O2 + 2 NaOH → (C6H5CO)2O2 + 2 NaCl + 2 H2O
過氧化物中的氧-氧鍵很弱。因此過氧化苯甲醯很容易發生均裂(對稱裂變),形成自由基:
- (C6H5CO)2O2 → 2 C
6H
5CO•
2
符號•表示其結果是自由基,即含有至少一個不成對的電子。此類物質具有高反應性。均解通常是經加熱引起。過氧化苯甲醯的半衰期在92°C下為一小時。在131°C時則縮減為一分鐘。[17]
科學家於1901年觀察到該化合物會導致愈創木酊劑變成藍色,顯示有氧氣釋放。[18]美國藥學家Arthur Solomon Loevenhart於1905報告其使用過氧化苯甲醯成功治療各種皮膚病,包括灼傷、慢性靜脈曲張和癬菌性鬚部感染。他在報告中提到於動物實驗中,該化合物的毒性相對較低。[19][6][20]
於1929年有使用過氧化苯甲醯治療傷口的建議,1934年有使用過氧化苯甲醯治療尋常性鬚瘡和壞死性粟粒性毛囊炎的建議。[20]然而當時的製劑品質往往會令人產生疑慮。[6]此藥物於1960年在美國正式被核准用於治療痤瘡。[6]
聚合
過氧化苯甲醯主要被用作自由基引發劑來引發鍊式聚合反應,[4]這些反應常用於製造聚酯和聚甲基丙烯酸甲酯 (PMMA) 樹脂以及牙科用黏合劑和牙體復形劑。[21]過氧化苯甲醯是用於此目的有機過氧化物中最重要的一種,是甚為危險過氧化丁酮的相對安全替代品。[22][23]過氧化苯甲醯也用於將橡膠硫化,以及作為某些醋酸纖維紗線的整理劑。[21]
其他用途
過氧化苯甲醯可有效治療痤瘡,而不會引起抗生素抗藥性。[24][25]它可與水楊酸、硫磺、紅黴素、克林黴素,或是阿達帕林(一種合成類視黃醇)合併使用。兩種常見的複方藥物包括過氧化苯甲醯/克林黴素,和阿達帕林/過氧化苯甲醯,阿達帕林是一種化學上穩定的類視黃醇,可與過氧化苯甲醯[26]聯合使用。過氧化苯甲醯/克林黴素和過氧化苯甲醯/水楊酸等複方產品似乎比單獨使用過氧化苯甲醯有較佳的治療痤瘡效果。[25]類視黃醇/過氧化苯甲醯組成的複方藥物於2021年在美國獲准用於醫療用途。
用於治療痤瘡的過氧化苯甲醯通常以凝膠、乳膏或液體的形式施用於受影響的區域,濃度從2.5%到5.0%,最高可達10%。[24]沒有強而有力的證據支持較高濃度會比較低濃度更為有效。[24]
作用機轉
傳統上過氧化苯甲醯被認為具有三重治療痤瘡的活性 - 它能控油、溶解粉刺,並抑制痤瘡丙酸桿菌(導致痤瘡的主要細菌)生長。[24][27]一般來說,尋常性痤瘡是一種激素介導的皮脂腺和毛囊發炎。激素變化導致角蛋白和皮脂分泌增加,而阻塞毛孔引流。痤瘡丙酸桿菌具有許多分解酶,可分解皮脂中的蛋白質和脂質,引起發炎反應。過氧化苯甲醯的自由基反應可分解此類角蛋白,而暢通皮脂排出(粉刺溶解)。它可引起痤瘡丙酸桿菌的非特異性過氧化,具有殺菌作用,[6]因此被認為可減少皮脂產生,但文獻中對此存有不同看法。[27][28]
一些證據顯示過氧化苯甲醯也具抗發炎作用。在體積微摩爾濃度下,它可防止嗜中性球釋放活性氧(這是痤瘡發炎反應的過程之一)。[28]
副作用
將過氧化苯甲醯塗在皮膚上可能會導致發紅、有灼燒感和不適的感覺。這種副作用和使用劑量多寡有關聯。[8][12]
由於可能有前述的副作用,建議先從低濃度的製劑開始使用,隨皮膚逐漸產生耐受性後,再升高濃度。通常在連續使用幾週後,皮膚敏感會消失。[28][29]避免使用具刺激性潔面乳並在接受陽光照射前塗抹防曬乳也可降低不適感。[29]
每五百人中就有一人對過氧化苯甲醯過敏,容易出現灼熱感、發癢、結痂,甚至可能會有水腫。大約三分之一使用者在暴露於紫外線下時會出現光毒性。[30]
劑量
在美國,用於治療痤瘡的處方藥和非處方藥製劑中過氧化苯甲醯的典型濃度為2.5%至10%。[31]
其他醫療用途
過氧化苯甲醯有在牙科中用作牙齒美白產品的案例。[32]
安全性
爆炸風險
過氧化苯甲醯與其他有機過氧化物一樣具有潛在爆炸性,[33]且在無外部引燃的情況下即可起火。純過氧化苯甲醯的危險性較高,因此通常會以溶液或糊狀的形式存在。例如化妝品中僅含有少量過氧化苯甲醯,不具爆炸風險。
毒性
過氧化苯甲醯與皮膚接觸後會分解,產生苯甲酸和氧氣,這兩種物質都無很強的毒性。[34]
有關過氧化苯甲醯的致癌潛力已被研究過。 一篇發表於1981年《科學》雜誌上的研究報告提出雖然過氧化苯甲醯不是致癌物,但在腫瘤起始時使用,確實會促進癌細胞生長。報告的結論是,"建議謹慎使用過氧化苯甲醯,及其他會產生自由基的化合物"。[35]
一份由國際癌症研究機構(IARC)於1999年發表,對致癌性研究的審查提出沒有令人信服的證據表明過氧化苯甲醯痤瘡藥物與人類皮膚癌有關聯。然而於一些動物研究已發現此種化合物可充當致癌物質,且會增強已知致癌物質的作用。[21]
過氧化苯甲醯在溫度高於50°C時會分解成致癌物質 - 苯。[36][37]
刺激皮膚
於1977年所做的一項人體最大化(HMT)測試,使用5%和10%過氧化苯甲醯含量的配方,有76%的受試者發生接觸致敏反應。[38]
美國國立職業安全與健康研究所制定有職業性接觸過氧化苯甲醯的建議標準。[39]
藥物沾染
痤瘡藥物接觸衣物或毛髮,如果藥物仍然潮濕時可能會立即導致永久性脫色。即使是間接接觸(例如接觸到用來洗滌含有過氧化苯甲醯衛生用品的毛巾)也會發生漂白作用。[40]
參考文獻
- ^ Epsolay- benzoyl peroxide cream. DailyMed. 2022-04-25 [2022-05-15]. (原始内容存档于2022-05-16).
- ^ Epsolay- benzoyl peroxide cream. DailyMed. 2022-05-05 [2022-06-19]. (原始内容存档于2022-06-20).
- ^ Template:BlueBook2013
- ^ 4.0 4.1 Peroxy Compounds, Organic, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a19_199
- ^ 5.0 5.1 Stellman JM. Encyclopaedia of Occupational Health and Safety: Guides, indexes, directory. International Labour Organization. 1998: 104. ISBN 978-92-2-109817-1. (原始内容存档于2017-09-18) (英语).
- ^ 6.0 6.1 6.2 6.3 6.4 Plewig G, Kligman AM. ACNE and ROSACEA 3. Springer Science & Business Media. 2012: 613. ISBN 978-3-642-59715-2. (原始内容存档于2017-09-18) (英语).
- ^ 7.0 7.1 Pommerville JC. Alcamo's Fundamentals of Microbiology: Body Systems. Jones & Bartlett Publishers. 2012: 214. ISBN 978-1-4496-0595-7. (原始内容存档于2017-09-18) (英语).
- ^ 8.0 8.1 World Health Organization. Stuart MC, Kouimtzi M, Hill SR , 编. WHO Model Formulary 2008. World Health Organization. 2009: 307–308. ISBN 978-92-4-154765-9. hdl:10665/44053.
- ^ 9.0 9.1 British national formulary : BNF 69 69. British Medical Association. 2015: 820. ISBN 978-0-85711-156-2.
- ^ Braun-Falco O, Plewig G, Wolff HH, Burgdorf W. Dermatology 2. Springer Science & Business Media. 2012: 1039. ISBN 978-3-642-97931-6. (原始内容存档于2017-09-18) (英语).
- ^ World Health Organization. The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. 2023. hdl:10665/371090 . WHO/MHP/HPS/EML/2023.02.
- ^ 12.0 12.1 Hamilton R. Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. 2015: 173. ISBN 978-1-284-05756-0.
- ^ The Top 300 of 2021. ClinCalc. [2024-01-14]. (原始内容存档于2024-01-15).
- ^ Benzoyl Peroxide - Drug Usage Statistics. ClinCalc. [2024-01-14].
- ^ 15.0 15.1 Brodie BC. Ueber die Bildung der Hyperoxyde organischer Säureradicale [On the Formation of the Peroxides of Organic Acid Radicals]. Justus Liebigs Ann. Chem. 1858, 108: 79–83 [2019-07-02]. doi:10.1002/jlac.18581080117. (原始内容存档于2020-11-29).
- ^ McBride JM, Vary MW. Radical pair in crystalline dibenzoyl peroxide evidence for triplet ground states. Tetrahedron. 1982, 38 (6): 765–775. doi:10.1016/0040-4020(82)80157-9.
- ^ Li III H. Chapter 2 (PDF). Synthesis, Characterization and Properties of Vinyl Ester Matrix Resins (学位论文). University of Vermont. 1998 [2007-02-17]. hdl:10919/30521. (原始内容存档于2006-09-20).
- ^ Kastle JH, Loevenhart AS. On the Nature of Certain Oxidizing Ferments. American Chemical Journal. 1901, 2: 539–566.
- ^ Loevenhart AS. Benzoylsuperoxyds, ein neues therapeutisches Agens. Therap Monatscheftel. 1905, 12: 426–428 (German).
- ^ 20.0 20.1 Merker PC. Benzoyl peroxide: a history of early research and researchers. International Journal of Dermatology. March 2002, 41 (3): 185–8. PMID 12010349. S2CID 24091844. doi:10.1046/j.1365-4362.2002.01371.x.
- ^ 21.0 21.1 21.2 International Agency for Research on Cancer (1999): "Benzoyl peroxide". in Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide 互联网档案馆的存檔,存档日期2020-07-15.. Monographs on the Evaluation of Carcinogenic Risks to Humans, number 71, pages 345–358. ISBN 92-832-1271-1
- ^ Initiation By Diacyl Peroxides. Polymer Properties Database. [2018-10-19]. (原始内容存档于2018-10-19).
- ^ Error - Evonik Industries AG (PDF). [2011-04-12]. (原始内容存档于2021-08-29).
- ^ 24.0 24.1 24.2 24.3 Simonart T. Newer approaches to the treatment of acne vulgaris. American Journal of Clinical Dermatology. December 2012, 13 (6): 357–64. PMID 22920095. S2CID 12200694. doi:10.2165/11632500-000000000-00000.
- ^ 25.0 25.1 Seidler EM, Kimball AB. Meta-analysis comparing efficacy of benzoyl peroxide, clindamycin, benzoyl peroxide with salicylic acid, and combination benzoyl peroxide/clindamycin in acne. Journal of the American Academy of Dermatology. July 2010, 63 (1): 52–62. PMID 20488582. doi:10.1016/j.jaad.2009.07.052.
- ^ Tolaymat L, Dearborn H, Zito PM. Adapalene. StatPearls. Treasure Island (FL): StatPearls Publishing. 2022 [2022-07-24]. PMID 29494115.
- ^ 27.0 27.1 Cotterill JA. Benzoyl peroxide. Acta Dermato-Venereologica. Supplementum. 1 January 1980, 89: 57–63. PMID 6162349. doi:10.2340/00015555895763 .
- ^ 28.0 28.1 28.2 Worret WI, Fluhr JW. [Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid] [Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid]. Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology. April 2006, 4 (4): 293–300. PMID 16638058. S2CID 6924764. doi:10.1111/j.1610-0387.2006.05931.x (German).
- ^ 29.0 29.1 Alldredge BK, Koda-Kimble MA, Young LY (编). Applied Therapeutics: The Clinical Use of Drugs 10th. Baltimore: Wolters Kluwer Health/Lippincott Williams & Wilkins. 2013: 949. ISBN 978-1-60913-713-7.
- ^ Jeanmougin M, Pedreiro J, Bouchet J, Civatte J. [Phototoxic activity of 5% benzoyl peroxide in man. Use of a new methodology]. Dermatologica. 1983-01-01, 167 (1): 19–23. PMID 6628794. doi:10.1159/000249739.
- ^ Grobel, Hana; Murphy, Sarah A. Chapter 77 - Acne Vulgaris and Acne Rosacea,Integrative Medicine (Fourth Edition). 2018: 1-2 [2024-04-20].
- ^ FACTS ON TEETH WHITENING. World of Dentristry. [2024-04-20].
- ^ Cartwright H. Chemical Safety Data: Benzoyl peroxide. Oxford University. 2005-03-17 [2011-08-13]. (原始内容存档于2010-10-12).
- ^ Benzoyl peroxide (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, April 2004
- ^ Slaga TJ, Klein-Szanto AJ, Triplett LL, Yotti LP, Trosko KE. Skin tumor-promoting activity of benzoyl peroxide, a widely used free radical-generating compound. Science. August 1981, 213 (4511): 1023–5. Bibcode:1981Sci...213.1023S. PMID 6791284. doi:10.1126/science.6791284.
- ^ Kucera K, Zenzola N, Hudspeth A, Dubnicka M, Hinz W, Bunick CG, Dabestani A, Light DY. Benzoyl Peroxide Drug Products Form Benzene. Environmental Health Perspectives. March 2024, 132 (3): 37702. PMC 10939128 . PMID 38483533. doi:10.1289/EHP13984.
- ^ USP Statement on Third Party Laboratory Benzene Findings | USP. www.usp.org. [2024-03-16] (英语).
- ^ Leyden JJ, Kligman AM. Contact sensitization to benzoyl peroxide. Contact Dermatitis. October 1977, 3 (5): 273–5. PMID 145346. S2CID 33553359. doi:10.1111/j.1600-0536.1977.tb03674.x.
- ^ Criteria for a Recommended Standard: Occupational Exposure to Benzoyl Peroxide (77-166). CDC - NIOSH Publications and Products. 2014-06-06 [2016-07-15]. doi:10.26616/NIOSHPUB76128 . (原始内容存档于2016-08-09).
- ^ Bojar RA, Cunliffe WJ, Holland KT. The short-term treatment of acne vulgaris with benzoyl peroxide: effects on the surface and follicular cutaneous microflora. The British Journal of Dermatology. February 1995, 132 (2): 204–8. PMID 7888356. S2CID 22468429. doi:10.1111/j.1365-2133.1995.tb05014.x.
外部連結
- 国际化学品安全卡0225
- NIOSH Pocket Guide to Chemical Hazards. #0052. NIOSH.
- SIDS Initial Assessment Report from the Organisation for Economic Co-operation and Development (OECD)
- Organic Peroxide Producers Safety Division (OPPSD)
Template:E number infobox 920-929
|
臨床資料 | |
---|---|
商品名 | Benzac、Panoxyl及其他 |
其他名稱 | benzoperoxide、dibenzoyl peroxide (DBPO)及BPO |
AHFS/Drugs.com | 专业药物信息 |
MedlinePlus | a601026 |
核准狀況 | |
给药途径 | 外用藥物 |
ATC碼 | |
法律規範狀態 | |
法律規範 | |
识别信息 | |
CAS号 | 94-36-0 |
PubChem CID | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.002.116 |
化学信息 | |
化学式 | C14H10O4 |
摩尔质量 | 242.23 g·mol−1 |
3D模型(JSmol) | |
密度 | 1.334 g/cm3 |
熔点 | 103至105 °C(217至221 °F) 分解 |
水溶性 | 不佳 mg/mL (20 °C) |
| |
|
過氧化苯甲醯 (英語:Benzoyl peroxide)是種化合物(特別是種有機過氧化物),結構式為 (C
6H
5–C(=O)O–)
2,通常縮寫為(BzO)2。就結構而言,這分子可描述為透過過氧化物((–O–O–)連接的兩個苯甲醯基(C
6H
5–C(=O)–, Bz) 。呈白色固體粒狀,有微弱苯甲醛氣味,難溶於水,但可溶於丙酮、乙醇和許多其他有機溶劑。過氧化苯甲醯是種氧化劑,主要用於生產聚合物。[4]
過氧化苯甲醯主要用於生產塑膠[5]以及漂白麵粉、頭髮、塑膠和紡織品。[6][7]
因其具有漂白劑的功能,而被用來作醫藥和水消毒用途。[5][7]
過氧化苯甲醯做藥物使用時,主要是單獨,或是與其他治療方式聯合處理痤瘡。[8]有些製劑是將過氧化苯甲醯與克林黴素等抗生素混合使用。[9][10]它已被列入世界衛生組織基本藥物標準清單中。[11]此藥物為一種非處方藥,有通用名藥物於市面販售。[12][9]有牙科也使用過氧化苯甲醯作美白牙齒的用途。 此藥物於2021年是美國最常使用處方藥中排名第284,開立的處方箋數量超過70萬張。[13][14]
歷史
過氧化苯甲醯由德國化學家尤斯圖斯·馮·李比希於1858年首次製成,並撰寫有報告。[15]
結構和反應性
李比希最初於1858年將過氧化氫與苯甲醯氯反應而完成過氧化苯甲醯的合成,[15]反應可能以下方程式進行:
- 2 C6H5C(O)Cl + BaO2 → (C6H5CO)2O2 + BaCl2
過氧化苯甲醯通常由過氧化氫與苯甲醯氯在鹽基條件下反應製備。
- 2 C6H5COCl + H2O2 + 2 NaOH → (C6H5CO)2O2 + 2 NaCl + 2 H2O
過氧化物中的氧-氧鍵很弱。因此過氧化苯甲醯很容易發生均裂(對稱裂變),形成自由基:
- (C6H5CO)2O2 → 2 C
6H
5CO•
2
符號•表示其結果是自由基,即含有至少一個不成對的電子。此類物質具有高反應性。均解通常是經加熱引起。過氧化苯甲醯的半衰期在92°C下為一小時。在131°C時則縮減為一分鐘。[17]
科學家於1901年觀察到該化合物會導致愈創木酊劑變成藍色,顯示有氧氣釋放。[18]美國藥學家Arthur Solomon Loevenhart於1905報告其使用過氧化苯甲醯成功治療各種皮膚病,包括灼傷、慢性靜脈曲張和癬菌性鬚部感染。他在報告中提到於動物實驗中,該化合物的毒性相對較低。[19][6][20]
於1929年有使用過氧化苯甲醯治療傷口的建議,1934年有使用過氧化苯甲醯治療尋常性鬚瘡和壞死性粟粒性毛囊炎的建議。[20]然而當時的製劑品質往往會令人產生疑慮。[6]此藥物於1960年在美國正式被核准用於治療痤瘡。[6]
聚合
過氧化苯甲醯主要被用作自由基引發劑來引發鍊式聚合反應,[4]這些反應常用於製造聚酯和聚甲基丙烯酸甲酯 (PMMA) 樹脂以及牙科用黏合劑和牙體復形劑。[21]過氧化苯甲醯是用於此目的有機過氧化物中最重要的一種,是甚為危險過氧化丁酮的相對安全替代品。[22][23]過氧化苯甲醯也用於將橡膠硫化,以及作為某些醋酸纖維紗線的整理劑。[21]
其他用途
過氧化苯甲醯可有效治療痤瘡,而不會引起抗生素抗藥性。[24][25]它可與水楊酸、硫磺、紅黴素、克林黴素,或是阿達帕林(一種合成類視黃醇)合併使用。兩種常見的複方藥物包括過氧化苯甲醯/克林黴素,和阿達帕林/過氧化苯甲醯,阿達帕林是一種化學上穩定的類視黃醇,可與過氧化苯甲醯[26]聯合使用。過氧化苯甲醯/克林黴素和過氧化苯甲醯/水楊酸等複方產品似乎比單獨使用過氧化苯甲醯有較佳的治療痤瘡效果。[25]類視黃醇/過氧化苯甲醯組成的複方藥物於2021年在美國獲准用於醫療用途。
用於治療痤瘡的過氧化苯甲醯通常以凝膠、乳膏或液體的形式施用於受影響的區域,濃度從2.5%到5.0%,最高可達10%。[24]沒有強而有力的證據支持較高濃度會比較低濃度更為有效。[24]
作用機轉
傳統上過氧化苯甲醯被認為具有三重治療痤瘡的活性 - 它能控油、溶解粉刺,並抑制痤瘡丙酸桿菌(導致痤瘡的主要細菌)生長。[24][27]一般來說,尋常性痤瘡是一種激素介導的皮脂腺和毛囊發炎。激素變化導致角蛋白和皮脂分泌增加,而阻塞毛孔引流。痤瘡丙酸桿菌具有許多分解酶,可分解皮脂中的蛋白質和脂質,引起發炎反應。過氧化苯甲醯的自由基反應可分解此類角蛋白,而暢通皮脂排出(粉刺溶解)。它可引起痤瘡丙酸桿菌的非特異性過氧化,具有殺菌作用,[6]因此被認為可減少皮脂產生,但文獻中對此存有不同看法。[27][28]
一些證據顯示過氧化苯甲醯也具抗發炎作用。在體積微摩爾濃度下,它可防止嗜中性球釋放活性氧(這是痤瘡發炎反應的過程之一)。[28]
副作用
將過氧化苯甲醯塗在皮膚上可能會導致發紅、有灼燒感和不適的感覺。這種副作用和使用劑量多寡有關聯。[8][12]
由於可能有前述的副作用,建議先從低濃度的製劑開始使用,隨皮膚逐漸產生耐受性後,再升高濃度。通常在連續使用幾週後,皮膚敏感會消失。[28][29]避免使用具刺激性潔面乳並在接受陽光照射前塗抹防曬乳也可降低不適感。[29]
每五百人中就有一人對過氧化苯甲醯過敏,容易出現灼熱感、發癢、結痂,甚至可能會有水腫。大約三分之一使用者在暴露於紫外線下時會出現光毒性。[30]
劑量
在美國,用於治療痤瘡的處方藥和非處方藥製劑中過氧化苯甲醯的典型濃度為2.5%至10%。[31]
其他醫療用途
過氧化苯甲醯有在牙科中用作牙齒美白產品的案例。[32]
安全性
爆炸風險
過氧化苯甲醯與其他有機過氧化物一樣具有潛在爆炸性,[33]且在無外部引燃的情況下即可起火。純過氧化苯甲醯的危險性較高,因此通常會以溶液或糊狀的形式存在。例如化妝品中僅含有少量過氧化苯甲醯,不具爆炸風險。
毒性
過氧化苯甲醯與皮膚接觸後會分解,產生苯甲酸和氧氣,這兩種物質都無很強的毒性。[34]
有關過氧化苯甲醯的致癌潛力已被研究過。 一篇發表於1981年《科學》雜誌上的研究報告提出雖然過氧化苯甲醯不是致癌物,但在腫瘤起始時使用,確實會促進癌細胞生長。報告的結論是,"建議謹慎使用過氧化苯甲醯,及其他會產生自由基的化合物"。[35]
一份由國際癌症研究機構(IARC)於1999年發表,對致癌性研究的審查提出沒有令人信服的證據表明過氧化苯甲醯痤瘡藥物與人類皮膚癌有關聯。然而於一些動物研究已發現此種化合物可充當致癌物質,且會增強已知致癌物質的作用。[21]
過氧化苯甲醯在溫度高於50°C時會分解成致癌物質 - 苯。[36][37]
刺激皮膚
於1977年所做的一項人體最大化(HMT)測試,使用5%和10%過氧化苯甲醯含量的配方,有76%的受試者發生接觸致敏反應。[38]
美國國立職業安全與健康研究所制定有職業性接觸過氧化苯甲醯的建議標準。[39]
藥物沾染
痤瘡藥物接觸衣物或毛髮,如果藥物仍然潮濕時可能會立即導致永久性脫色。即使是間接接觸(例如接觸到用來洗滌含有過氧化苯甲醯衛生用品的毛巾)也會發生漂白作用。[40]
參考文獻
- ^ Epsolay- benzoyl peroxide cream. DailyMed. 2022-04-25 [2022-05-15]. (原始内容存档于2022-05-16).
- ^ Epsolay- benzoyl peroxide cream. DailyMed. 2022-05-05 [2022-06-19]. (原始内容存档于2022-06-20).
- ^ Template:BlueBook2013
- ^ 4.0 4.1 Peroxy Compounds, Organic, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a19_199
- ^ 5.0 5.1 Stellman JM. Encyclopaedia of Occupational Health and Safety: Guides, indexes, directory. International Labour Organization. 1998: 104. ISBN 978-92-2-109817-1. (原始内容存档于2017-09-18) (英语).
- ^ 6.0 6.1 6.2 6.3 6.4 Plewig G, Kligman AM. ACNE and ROSACEA 3. Springer Science & Business Media. 2012: 613. ISBN 978-3-642-59715-2. (原始内容存档于2017-09-18) (英语).
- ^ 7.0 7.1 Pommerville JC. Alcamo's Fundamentals of Microbiology: Body Systems. Jones & Bartlett Publishers. 2012: 214. ISBN 978-1-4496-0595-7. (原始内容存档于2017-09-18) (英语).
- ^ 8.0 8.1 World Health Organization. Stuart MC, Kouimtzi M, Hill SR , 编. WHO Model Formulary 2008. World Health Organization. 2009: 307–308. ISBN 978-92-4-154765-9. hdl:10665/44053.
- ^ 9.0 9.1 British national formulary : BNF 69 69. British Medical Association. 2015: 820. ISBN 978-0-85711-156-2.
- ^ Braun-Falco O, Plewig G, Wolff HH, Burgdorf W. Dermatology 2. Springer Science & Business Media. 2012: 1039. ISBN 978-3-642-97931-6. (原始内容存档于2017-09-18) (英语).
- ^ World Health Organization. The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. 2023. hdl:10665/371090 . WHO/MHP/HPS/EML/2023.02.
- ^ 12.0 12.1 Hamilton R. Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. 2015: 173. ISBN 978-1-284-05756-0.
- ^ The Top 300 of 2021. ClinCalc. [2024-01-14]. (原始内容存档于2024-01-15).
- ^ Benzoyl Peroxide - Drug Usage Statistics. ClinCalc. [2024-01-14].
- ^ 15.0 15.1 Brodie BC. Ueber die Bildung der Hyperoxyde organischer Säureradicale [On the Formation of the Peroxides of Organic Acid Radicals]. Justus Liebigs Ann. Chem. 1858, 108: 79–83 [2019-07-02]. doi:10.1002/jlac.18581080117. (原始内容存档于2020-11-29).
- ^ McBride JM, Vary MW. Radical pair in crystalline dibenzoyl peroxide evidence for triplet ground states. Tetrahedron. 1982, 38 (6): 765–775. doi:10.1016/0040-4020(82)80157-9.
- ^ Li III H. Chapter 2 (PDF). Synthesis, Characterization and Properties of Vinyl Ester Matrix Resins (学位论文). University of Vermont. 1998 [2007-02-17]. hdl:10919/30521. (原始内容存档于2006-09-20).
- ^ Kastle JH, Loevenhart AS. On the Nature of Certain Oxidizing Ferments. American Chemical Journal. 1901, 2: 539–566.
- ^ Loevenhart AS. Benzoylsuperoxyds, ein neues therapeutisches Agens. Therap Monatscheftel. 1905, 12: 426–428 (German).
- ^ 20.0 20.1 Merker PC. Benzoyl peroxide: a history of early research and researchers. International Journal of Dermatology. March 2002, 41 (3): 185–8. PMID 12010349. S2CID 24091844. doi:10.1046/j.1365-4362.2002.01371.x.
- ^ 21.0 21.1 21.2 International Agency for Research on Cancer (1999): "Benzoyl peroxide". in Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide 互联网档案馆的存檔,存档日期2020-07-15.. Monographs on the Evaluation of Carcinogenic Risks to Humans, number 71, pages 345–358. ISBN 92-832-1271-1
- ^ Initiation By Diacyl Peroxides. Polymer Properties Database. [2018-10-19]. (原始内容存档于2018-10-19).
- ^ Error - Evonik Industries AG (PDF). [2011-04-12]. (原始内容存档于2021-08-29).
- ^ 24.0 24.1 24.2 24.3 Simonart T. Newer approaches to the treatment of acne vulgaris. American Journal of Clinical Dermatology. December 2012, 13 (6): 357–64. PMID 22920095. S2CID 12200694. doi:10.2165/11632500-000000000-00000.
- ^ 25.0 25.1 Seidler EM, Kimball AB. Meta-analysis comparing efficacy of benzoyl peroxide, clindamycin, benzoyl peroxide with salicylic acid, and combination benzoyl peroxide/clindamycin in acne. Journal of the American Academy of Dermatology. July 2010, 63 (1): 52–62. PMID 20488582. doi:10.1016/j.jaad.2009.07.052.
- ^ Tolaymat L, Dearborn H, Zito PM. Adapalene. StatPearls. Treasure Island (FL): StatPearls Publishing. 2022 [2022-07-24]. PMID 29494115.
- ^ 27.0 27.1 Cotterill JA. Benzoyl peroxide. Acta Dermato-Venereologica. Supplementum. 1 January 1980, 89: 57–63. PMID 6162349. doi:10.2340/00015555895763 .
- ^ 28.0 28.1 28.2 Worret WI, Fluhr JW. [Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid] [Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid]. Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology. April 2006, 4 (4): 293–300. PMID 16638058. S2CID 6924764. doi:10.1111/j.1610-0387.2006.05931.x (German).
- ^ 29.0 29.1 Alldredge BK, Koda-Kimble MA, Young LY (编). Applied Therapeutics: The Clinical Use of Drugs 10th. Baltimore: Wolters Kluwer Health/Lippincott Williams & Wilkins. 2013: 949. ISBN 978-1-60913-713-7.
- ^ Jeanmougin M, Pedreiro J, Bouchet J, Civatte J. [Phototoxic activity of 5% benzoyl peroxide in man. Use of a new methodology]. Dermatologica. 1983-01-01, 167 (1): 19–23. PMID 6628794. doi:10.1159/000249739.
- ^ Grobel, Hana; Murphy, Sarah A. Chapter 77 - Acne Vulgaris and Acne Rosacea,Integrative Medicine (Fourth Edition). 2018: 1-2 [2024-04-20].
- ^ FACTS ON TEETH WHITENING. World of Dentristry. [2024-04-20].
- ^ Cartwright H. Chemical Safety Data: Benzoyl peroxide. Oxford University. 2005-03-17 [2011-08-13]. (原始内容存档于2010-10-12).
- ^ Benzoyl peroxide (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, April 2004
- ^ Slaga TJ, Klein-Szanto AJ, Triplett LL, Yotti LP, Trosko KE. Skin tumor-promoting activity of benzoyl peroxide, a widely used free radical-generating compound. Science. August 1981, 213 (4511): 1023–5. Bibcode:1981Sci...213.1023S. PMID 6791284. doi:10.1126/science.6791284.
- ^ Kucera K, Zenzola N, Hudspeth A, Dubnicka M, Hinz W, Bunick CG, Dabestani A, Light DY. Benzoyl Peroxide Drug Products Form Benzene. Environmental Health Perspectives. March 2024, 132 (3): 37702. PMC 10939128 . PMID 38483533. doi:10.1289/EHP13984.
- ^ USP Statement on Third Party Laboratory Benzene Findings | USP. www.usp.org. [2024-03-16] (英语).
- ^ Leyden JJ, Kligman AM. Contact sensitization to benzoyl peroxide. Contact Dermatitis. October 1977, 3 (5): 273–5. PMID 145346. S2CID 33553359. doi:10.1111/j.1600-0536.1977.tb03674.x.
- ^ Criteria for a Recommended Standard: Occupational Exposure to Benzoyl Peroxide (77-166). CDC - NIOSH Publications and Products. 2014-06-06 [2016-07-15]. doi:10.26616/NIOSHPUB76128 . (原始内容存档于2016-08-09).
- ^ Bojar RA, Cunliffe WJ, Holland KT. The short-term treatment of acne vulgaris with benzoyl peroxide: effects on the surface and follicular cutaneous microflora. The British Journal of Dermatology. February 1995, 132 (2): 204–8. PMID 7888356. S2CID 22468429. doi:10.1111/j.1365-2133.1995.tb05014.x.
外部連結
- 国际化学品安全卡0225
- NIOSH Pocket Guide to Chemical Hazards. #0052. NIOSH.
- SIDS Initial Assessment Report from the Organisation for Economic Co-operation and Development (OECD)
- Organic Peroxide Producers Safety Division (OPPSD)
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