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, Sublimaze and others
Drugs.com	Monograph
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	TD, IM, IV, oral transmucosal, sublingual, buccal
合法狀態
合法状态	AU: 受管控 (S8); UK: Class A; US: Schedule II; 处方药（℞-only）;
药代动力学数据
生物利用度	92% (transdermal); 89% (intranasal); 50% (buccal); 33% (ingestion)
蛋白结合度	80–85%
代谢	hepatic, primarily by CYP3A4
生物半衰期	(IV)= 10-20 mins (T1/2 β); 2-4 hours (T1/2 ɣ); Intranasal = 6.5 mins; Transdermal = 20–27 h
排泄	60% 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)CCC2=CC=CC=C2)C3=CC=CC=C3 ;
	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）
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提示：本条目的主题不是芬普尼。

维基百科中的醫療相关内容仅供参考，詳見醫學聲明。如需专业意见请咨询专业人士。

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^[3]。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。^[4] 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。^[5]

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。 ^[6] 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。^[7] 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）,^[8] 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。^[9]^[10] 截至2012年，芬太尼是醫學中使用最廣泛的合成鴉片類藥物。^[11] 2013年，全球共使用了1700公斤（3,750磅）芬太尼。^[12]

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。^[5]^[13]^[14] 不當醫療使用也導致了死亡案例。 ^[15] 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。^[16]

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。^[17]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”。^[18]

“芬太尼棒棒糖”的包装及样品，400 mg

另見[编辑]

卡芬太尼（Carfentanil）

参考资料[编辑]

^ Janssen Pharmaceuticals (Duragesic)
^ Hess R, Stiebler G, Herz A. Pharmacokinetics of fentanyl in man and the rabbit. Eur. J. Clin. Pharmacol. June 1972, 4 (3): 137–41. PMID 4655287. doi:10.1007/BF00561135.
^ 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].
^ ^5.0 ^5.1 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].

外部連結[编辑]

维基共享资源中相关的多媒体资源：芬太尼

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

[1] Janssen Pharmaceuticals (Duragesic)

[pmid4655287-2] Hess R, Stiebler G, Herz A. Pharmacokinetics of fentanyl in man and the rabbit. Eur. J. Clin. Pharmacol. June 1972, 4 (3): 137–41. PMID 4655287. doi:10.1007/BF00561135.

[3] 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-4] DrugFacts: Fentanyl. National Institute on Drug Abuse, US National Institutes of Health. June 2016 [19 March 2017].

[cnd-5] 5.0 ^5.1 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].

[pmid1517629-6] 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.

[pmid15771410-7] 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）.

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

[9] Subsys (fentanyl sublingual spray).

[10] 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].

[11] Fentanyl and Analogues.

[UN2015-12] Narcotic Drugs 2014 (pdf). International Narcotics Control Board. 2015: 21. ISBN 9789210481571.

[Globalnews.ca-1-13] ‘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-14] Vestal, Christine. As Fentanyl Deaths Spike, States and CDC Respond. Pew Charitable Trusts. 1 April 2016 [13 July 2016].

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

[Springer-16] 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.

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

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

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芬太尼

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