芬太尼

**芬太尼**
系统（IUPAC）命名名称
	N-(1-(2-Phenylethyl)-4-piperidinyl)-N-phenylpropanamide
临床数据
商品名	Actiq, Duragesic, Fentora, others
Drugs.com	Monograph
医疗法规	EU EMA: yes;
妊娠分级	AU: C ; US: C (不排除有风险的可能) ; ;
依赖性	Very high
给药途径	Buccal, epidural, IM, IT, IV, sublingual, skin patch
合法狀態
合法状态	AU: 受管控 (S8) ; CA: Schedule I ; DE: Anlage III ; UK: Class A ; US: Schedule II ; CN: 处方药 ;
药代动力学数据
生物利用度	92%（經皮膚吸收）; 89%（intranasal）; 50%（buccal）; 33%（口服）
蛋白结合度	80－85%
代谢	肝，主要通過CYP3A4
開始出現藥效	5分鐘
生物半衰期	IV: 6分鐘 (T1/2 α); 1小時 (T1/2 β); 16小時 (T1/2 ɣ); Intranasal: 6.5小時; Transdermal: 20－27小時; Sublingual/buccal（單劑量）：2.6－13.5小時
作用时间	IV: 30－60分鐘
排泄	Mostly urinary (metabolites, <10% unchanged drug)
识别信息
CAS注册号	437-38-7
ATC代码	N01AH01 N02AB03
PubChem	CID 3345
IUPHAR/BPS（英语：IUPHAR/BPS）	1626
DrugBank	DB00813
ChemSpider	3228
UNII	UF599785JZ
KEGG	D00320
ChEBI	CHEBI:119915
ChEMBL（英语：ChEMBL）	CHEMBL596
化学信息
化学式	C22H28N2O
摩尔质量	336.471 g/mol
	SMILES O=C(CC)N(C1CCN(CC1)CCc2ccccc2)c3ccccc3; ;
	InChI InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3 ; Key:PJMPHNIQZUBGLI-UHFFFAOYSA-N ;
物理性质
熔点	87.5 °C（189.5 °F）
(verify)

芬太尼（英语：Fentanyl）是一種強效的、類鴉片止痛劑，起效迅速而作用時間極短^[4]。它是腦中μ-鴉片受體（英语：μ-opioid receptor）的強力激動劑。芬太尼比嗎啡效力高50至100倍。^[5]但一些為了模擬芬太尼之藥理作用的芬太尼類似物可能比嗎啡高出10,000倍。^[6]

歷史[编辑]

在哌替啶鹽酸鹽（也稱為哌替啶，市售為杜冷丁）的醫療使用開始後，保羅·揚森最先在1960年製造出芬太尼。^[7]揚森通過測定結構相關的藥物哌替啶的類似物用於鴉片樣物質活性，發展了芬太尼。^[8]芬太尼的廣泛使用引發了檸檬酸芬太尼的生產（鹽酸芬太尼和檸檬酸組合1：1化學計量），^[9]而使芬太尼在1960年代以商業名稱Sublimaze進入醫療用途作為全身麻醉劑。

在1990年代中期，芬太尼貼片先被用做安寧緩和醫療藥物。接下來的十年，又有了芬太尼棒棒糖、溶解片劑和可以被嘴巴裡頭的口腔黏膜吸收掉的舌下噴劑。^[10]^[11]截至2012年，芬太尼是醫學中使用最廣泛的合成鴉片類藥物。^[12]2013年，全球共使用了1700公斤（3,750磅）芬太尼。^[13]

芬太尼也被用作娛樂性用藥，導致2000年至2017年數以千計的藥物過量死亡案例。^[6]^[14]^[15]不當醫療使用也導致了死亡案例。^[16]芬太尼具有相對較廣的治療指數（270），使其在仔細監測時成為非常安全的手術麻醉劑；然而，其效力需要仔細測量溶液中高度稀釋的芬太尼。^[17]

此外，2002年10月發生的莫斯科歌劇院脅持事件中，俄罗斯军警及阿尔法小组用其对歌剧院里的所有人麻醉后强攻，造成130人因芬太尼的不良反应死亡。^[18]军事上，美國空軍空降搜救組和瑞典军队的军医也曾使用过叫做“Actiq”的“芬太尼棒”。^[19]

“芬太尼棒棒糖”的包装及样品，400 mg

美国疾病控制与预防中心估計在2016年有超過20,000名美國人死於芬太尼及其類似結構化合物過量。^[20]

另見[编辑]

卡芬太尼（英语：Carfentanil）（Carfentanil）

參見[编辑]

参考资料[编辑]

^ ^1.0 ^1.1 Clinically Oriented Pharmacology 2. Quick Review of Pharmacology. 2010: 172.
^ ^2.0 ^2.1 ^2.2 Fentanyl, Fentanyl Citrate, Fentanyl Hydrochloride. The American Society of Health-System Pharmacists. [2017-12-08]. （原始内容存档于14 December 2017）.
^ Guideline for administration of fentanyl for pain relief in labour (PDF). RCP. [2015-10-07]. （原始内容存档 (PDF)于2016-03-04）. Onset of action after IV administration of Fentanyl is 3–5 minutes; duration of action is 30–60 minutes.
^ WCPI Focus on Pain Series: The Three Faces of Fentanyl. Aspi.wisc.edu. [2010-07-28]. （原始内容存档于2010-06-10）.
^ DrugFacts: Fentanyl. National Institute on Drug Abuse, US National Institutes of Health. June 2016 [19 March 2017].
^ ^6.0 ^6.1 Commission on Narcotic Drugs takes decisive step to help prevent deadly fentanyl overdoses. Commission on Narcotic Drugs, United Nations Office on Drugs and Crime. 16 March 2017 [19 March 2017].
^ Stanley TH. The history and development of the fentanyl series. J Pain Symptom Manage. April 1992, 7 (3 Suppl): S3–7. PMID 1517629. doi:10.1016/0885-3924(92)90047-L.
^ Black J. A personal perspective on Dr. Paul Janssen (PDF). J. Med. Chem. March 2005, 48 (6): 1687–8. PMID 15771410. doi:10.1021/jm040195b. （原始内容 (PDF)存档于2007-10-10）.
^ DailyMed: About DailyMed. Dailymed.nlm.nih.gov. [2010-07-28].
^ Subsys (fentanyl sublingual spray).
^ Long Term Safety and Efficacy Study of Fentanyl Sublingual Spray for the Treatment of Breakthrough Cancer Pain – Full Text View. ClinicalTrials.gov. [2010-07-28].
^ Fentanyl and Analogues.
^ Narcotic Drugs 2014 (pdf). International Narcotics Control Board. 2015: 21. ISBN 9789210481571.
^ ‘It is a huge issue’: 145 fentanyl-related deaths in Alberta so far in 2015. globalnews.ca. August 11, 2015 [16 November 2015].
^ Vestal, Christine. As Fentanyl Deaths Spike, States and CDC Respond. Pew Charitable Trusts. 1 April 2016 [13 July 2016].
^ Serna, Joseph; Karlamangla, Soumya. Death toll rises to 9 in suspected fentanyl overdoses in Northern California. The Los Angeles Times. [2016-04-01].
^ Stanley, Theodore Henry; Petty, William Clayton. New Anesthetic Agents, Devices, and Monitoring Techniques. Springer. 1983-03-31 [20 October 2007]. ISBN 978-90-247-2796-4.
^ Moscow theatre siege:Questions remain unanswered BBC Retrieved on 2013-16-13
^ Shachtman, Noah. Airborne EMTs Shave Seconds to Save Lives in Afghanistan. Danger Room. Wired.com. September 10, 2009 [July 1, 2010].
^ Drug disruption major HSI focus in 2017. ice.gov.

外部連結[编辑]

Template:Xenobiotic-sensing receptor modulators（英语：Template:Xenobiotic-sensing receptor modulators）

[Cl2010-1] 1.0 ^1.1 Clinically Oriented Pharmacology 2. Quick Review of Pharmacology. 2010: 172.

[AHFS2017-2] 2.0 ^2.1 ^2.2 Fentanyl, Fentanyl Citrate, Fentanyl Hydrochloride. The American Society of Health-System Pharmacists. [2017-12-08]. （原始内容存档于14 December 2017）.

[3] Guideline for administration of fentanyl for pain relief in labour (PDF). RCP. [2015-10-07]. （原始内容存档 (PDF)于2016-03-04）. Onset of action after IV administration of Fentanyl is 3–5 minutes; duration of action is 30–60 minutes.

[4] WCPI Focus on Pain Series: The Three Faces of Fentanyl. Aspi.wisc.edu. [2010-07-28]. （原始内容存档于2010-06-10）.

[CDC-5] DrugFacts: Fentanyl. National Institute on Drug Abuse, US National Institutes of Health. June 2016 [19 March 2017].

[cnd-6] 6.0 ^6.1 Commission on Narcotic Drugs takes decisive step to help prevent deadly fentanyl overdoses. Commission on Narcotic Drugs, United Nations Office on Drugs and Crime. 16 March 2017 [19 March 2017].

[pmid1517629-7] Stanley TH. The history and development of the fentanyl series. J Pain Symptom Manage. April 1992, 7 (3 Suppl): S3–7. PMID 1517629. doi:10.1016/0885-3924(92)90047-L.

[pmid15771410-8] Black J. A personal perspective on Dr. Paul Janssen (PDF). J. Med. Chem. March 2005, 48 (6): 1687–8. PMID 15771410. doi:10.1021/jm040195b. （原始内容 (PDF)存档于2007-10-10）.

[9] DailyMed: About DailyMed. Dailymed.nlm.nih.gov. [2010-07-28].

[10] Subsys (fentanyl sublingual spray).

[11] Long Term Safety and Efficacy Study of Fentanyl Sublingual Spray for the Treatment of Breakthrough Cancer Pain – Full Text View. ClinicalTrials.gov. [2010-07-28].

[12] Fentanyl and Analogues.

[UN2015-13] Narcotic Drugs 2014 (pdf). International Narcotics Control Board. 2015: 21. ISBN 9789210481571.

[Globalnews.ca-1-14] ‘It is a huge issue’: 145 fentanyl-related deaths in Alberta so far in 2015. globalnews.ca. August 11, 2015 [16 November 2015].

[Pew-vesta-15] Vestal, Christine. As Fentanyl Deaths Spike, States and CDC Respond. Pew Charitable Trusts. 1 April 2016 [13 July 2016].

[16] Serna, Joseph; Karlamangla, Soumya. Death toll rises to 9 in suspected fentanyl overdoses in Northern California. The Los Angeles Times. [2016-04-01].

[Springer-17] Stanley, Theodore Henry; Petty, William Clayton. New Anesthetic Agents, Devices, and Monitoring Techniques. Springer. 1983-03-31 [20 October 2007]. ISBN 978-90-247-2796-4.

[18] Moscow theatre siege:Questions remain unanswered BBC Retrieved on 2013-16-13

[19] Shachtman, Noah. Airborne EMTs Shave Seconds to Save Lives in Afghanistan. Danger Room. Wired.com. September 10, 2009 [July 1, 2010].

[20] Drug disruption major HSI focus in 2017. ice.gov.

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芬太尼

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