安非拉酮

安非拉酮
臨床資料
商品名（英語：Drug nomenclature）	Tenuate、Tepanil、Nobesine和其它
其他名稱	二乙胺苯酮、二乙胺苯丙酮、二乙基卡西酮
AHFS/Drugs.com	Monograph
MedlinePlus	a682037
核准狀況	美 DailyMed: Diethylpropion;
懷孕分級	澳: B2 ; ;
給藥途徑	口服
ATC碼	A08AA03 (WHO) ;
法律規範狀態
法律規範	澳：限醫生處方（S4）; 加：Schedule G (CDSA IV); 德：Prescription only (Anlage III for higher doses); 歐：Rx-only; 英：Class C; 美：附表IV;
藥物動力學數據
生物半衰期	4-6小時 (代謝物)
排泄途徑	尿液 (>75%)
識別資訊
	IUPAC命名法 (RS)-2-diethylamino-1-phenylpropan-1-one; ;
CAS編號	134-80-5
PubChem CID	7029;
IUPHAR/BPS	7161;
DrugBank	DB00937 ;
ChemSpider	6762 ;
UNII	19V2PL39NG;
KEGG	D07444 ;
ChEBI	CHEBI:4530 ;
ChEMBL	ChEMBL1194666 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID6022929 ;
ECHA InfoCard	100.001.836
化學資訊
化學式	C13H19NO
摩爾質量	205.30 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
手性	外消旋體
	SMILES O=C(c1ccccc1)C(N(CC)CC)C;
	InChI InChI=1S/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3 ; Key:XXEPPPIWZFICOJ-UHFFFAOYSA-N ;

安非拉酮（英語：Amfepramone）是苯乙胺、苯丙胺和卡西酮類的興奮劑藥物，用作食慾抑制劑。^[7]^[8]它用於肥胖的短期管理，以及飲食和生活方式的改變。^[7]安非拉酮與抗抑鬱藥和戒煙助劑安非他酮在化學上的關係最密切，安非他酮與納曲酮組合後也被開發為減肥藥。^[9]

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藥理學

安非拉酮本身對單胺轉運蛋白沒有任何親和力，而是作為乙卡西酮的前藥發揮作用。^[10]乙卡西酮（包括安非拉酮）是一種非常弱的多巴胺能和血清素能，相比之下，去甲腎上腺素的作用分別強大約10倍和20倍。^[10]因此，乙卡西酮和安非拉酮基本上可以被認為是被稱為去甲腎上腺素釋放劑的一類藥物的成員。

化學

安非拉酮可由苯丙酮通過溴化反應合成，然後與二乙胺反應。^[11]^[12]

社會與文化

名稱

另一個醫學上使用的名稱是二乙胺苯酮（Diethylpropion，BAN和ANN）。化學名稱包括：α-甲基-β-酮基-N,N-二乙基苯乙胺、N,N-二乙基-β-酮苯丙胺和N,N-二乙基卡西酮。商品名包括：Anorex、Linea、Nobesine、Prefamone、Regenon、Tepanil和Tenuate。

法律地位

安非拉酮在美國被歸類為附表IV受管制物質。在英國，安非拉酮是一種 C 類藥物，^[13]作為一種藥物，它是一種需要安全保管的附表3管制藥物。

自2022年6月起，歐洲藥品管理局安全委員會建議撤銷安非拉酮的上市許可。^[14]^[5]

在中國，安非拉酮是一類管制精神藥品，禁止進境^[15]

1999年5月13日，中國國家藥品監督管理局撤銷了中國衛生部在1993年唯一批准的生產安非拉酮的單位山東濰坊製藥二廠的安非拉酮的批准文號^[16]

娛樂用途

幾項安非拉酮研究的作者聲稱，該物質引起使用者成癮的可能性相對較低。^[17]^[18]^[3]^[19]

參考資料

[1]
Tenuate Product information. Health Canada. 25 April 2012 [3 August 2022]. （原始內容存檔於4 August 2022）.
[2]
Nobesine Product information. Health Canada. 25 April 2012 [3 August 2022]. （原始內容存檔於4 August 2022）.
[3]
Tepanil (diethylpropion hydrochloride) tablet, extended release. Dailymed. National Institutes of Health. [4 August 2022]. （原始內容存檔於8 May 2021）.
[4]
https://www.ema.europa.eu/documents/psusa/amfepramone-list-nationally-authorised-medicinal-products-psusa/00000138/202006_en.pdf 互聯網檔案館的存檔，存檔日期27 August 2021. ^[裸網址]
[5]
Amfepramone-containing medicinal products. European Medicines Agency (EMA). 12 February 2021 [12 February 2021]. （原始內容存檔於7 March 2021）.
[6]
SPC-DOC_PL 16133-0001 (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011 [18 July 2014].^{[永久失效連結]}
[7]
Brayfield A (編). Diethylpropion Hydrochloride. Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. 30 January 2013 [18 July 2014]. （原始內容存檔於27 August 2021）.
[8]
TGA Approved Terminology for Medicines, Section 1 – Chemical Substances (PDF). Therapeutic Goods Administration (Tga) (Therapeutic Goods Administration, Department of Health and Ageing, Australian Government). July 1999: 42 [18 July 2014]. （原始內容存檔 (PDF)於11 February 2014）.
[9]
Arias HR, Santamaría A, Ali SF. Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. New Concepts of Psychostimulant Induced Neurotoxicity. International Review of Neurobiology 88. 2009: 223–55. ISBN 9780123745040. PMID 19897080. doi:10.1016/S0074-7742(09)88009-4.
[10]
Rothman RB, Baumann MH. Therapeutic potential of monoamine transporter substrates. Current Topics in Medicinal Chemistry. 2006, 6 (17): 1845–59 [7 September 2020]. PMID 17017961. doi:10.2174/156802606778249766. （原始內容存檔於23 October 2020）.
[11]
US patent 3001910,Schutte J,「Anorexigenic Propiophenones」,發行於1961-09-26,指定於Temmler-Werke
[12]
Hyde JF, Browning E, Adams R. Synthetic Homologs of d,l-Ephedrine. Journal of the American Chemical Society. 1928, 50 (8): 2287–2292. doi:10.1021/ja01395a032.
[13]
Class C Drugs. Schedule 2 Controlled Drugs. UK Legislation. [7 February 2012]. （原始內容存檔於14 November 2012）.
[14]
EMA recommends withdrawal of marketing authorisation for amfepramone medicines. European Medicines Agency (EMA). 10 June 2022 [10 June 2022]. （原始內容存檔於10 June 2022）.
[15]
苏州海关在邮包中查获一类管制精神药品安非拉酮. 中華人民共和國南京海關.
[16]
國家藥品監督管理局關於撤銷安非拉酮批准文號的通知
[17]
Cohen S. Diethylpropion (tenuate): an infrequently abused anorectic. Psychosomatics. 1977, 18 (1): 28–33. PMID 850721. doi:10.1016/S0033-3182(77)71101-6 .
[18]
Jasinski DR, Krishnan S. Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse. Journal of Psychopharmacology. June 2009, 23 (4): 419–27. PMID 19329547. S2CID 6138292. doi:10.1177/0269881109103113.
[19]
Caplan J. Habituation to diethylpropion (Tenuate). Canadian Medical Association Journal. May 1963, 88: 943–4. PMC 1921278 . PMID 14018413.

外部連結

Amfepramone. Drug Information Portal. U.S. National Library of Medicine. [2023-02-23]. （原始內容存檔於2022-09-20）.

[1] [1]
Tenuate Product information. Health Canada. 25 April 2012 [3 August 2022]. （原始內容存檔於4 August 2022）.

[2] [2]
Nobesine Product information. Health Canada. 25 April 2012 [3 August 2022]. （原始內容存檔於4 August 2022）.

[Tepanil_FDA_label-3] [3]
Tepanil (diethylpropion hydrochloride) tablet, extended release. Dailymed. National Institutes of Health. [4 August 2022]. （原始內容存檔於8 May 2021）.

[4] [4]
https://www.ema.europa.eu/documents/psusa/amfepramone-list-nationally-authorised-medicinal-products-psusa/00000138/202006_en.pdf 互聯網檔案館的存檔，存檔日期27 August 2021. ^[裸網址]

[EU_Amfepramone-5] [5]
Amfepramone-containing medicinal products. European Medicines Agency (EMA). 12 February 2021 [12 February 2021]. （原始內容存檔於7 March 2021）.

[MHRA-6] [6]
SPC-DOC_PL 16133-0001 (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011 [18 July 2014].^{[永久失效連結]}

[MD-7] [7]
Brayfield A (編). Diethylpropion Hydrochloride. Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. 30 January 2013 [18 July 2014]. （原始內容存檔於27 August 2021）.

[8] [8]
TGA Approved Terminology for Medicines, Section 1 – Chemical Substances (PDF). Therapeutic Goods Administration (Tga) (Therapeutic Goods Administration, Department of Health and Ageing, Australian Government). July 1999: 42 [18 July 2014]. （原始內容存檔 (PDF)於11 February 2014）.

[9] [9]
Arias HR, Santamaría A, Ali SF. Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. New Concepts of Psychostimulant Induced Neurotoxicity. International Review of Neurobiology 88. 2009: 223–55. ISBN 9780123745040. PMID 19897080. doi:10.1016/S0074-7742(09)88009-4.

[pmid17017961-10] [10]
Rothman RB, Baumann MH. Therapeutic potential of monoamine transporter substrates. Current Topics in Medicinal Chemistry. 2006, 6 (17): 1845–59 [7 September 2020]. PMID 17017961. doi:10.2174/156802606778249766. （原始內容存檔於23 October 2020）.

[11] [11]
US patent 3001910,Schutte J,「Anorexigenic Propiophenones」,發行於1961-09-26,指定於Temmler-Werke

[12] [12]
Hyde JF, Browning E, Adams R. Synthetic Homologs of d,l-Ephedrine. Journal of the American Chemical Society. 1928, 50 (8): 2287–2292. doi:10.1021/ja01395a032.

[13] [13]
Class C Drugs. Schedule 2 Controlled Drugs. UK Legislation. [7 February 2012]. （原始內容存檔於14 November 2012）.

[14] [14]
EMA recommends withdrawal of marketing authorisation for amfepramone medicines. European Medicines Agency (EMA). 10 June 2022 [10 June 2022]. （原始內容存檔於10 June 2022）.

[15] [15]
苏州海关在邮包中查获一类管制精神药品安非拉酮. 中華人民共和國南京海關.

[16] [16]
國家藥品監督管理局關於撤銷安非拉酮批准文號的通知

[17] [17]
Cohen S. Diethylpropion (tenuate): an infrequently abused anorectic. Psychosomatics. 1977, 18 (1): 28–33. PMID 850721. doi:10.1016/S0033-3182(77)71101-6 .

[18] [18]
Jasinski DR, Krishnan S. Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse. Journal of Psychopharmacology. June 2009, 23 (4): 419–27. PMID 19329547. S2CID 6138292. doi:10.1177/0269881109103113.

[19] [19]
Caplan J. Habituation to diethylpropion (Tenuate). Canadian Medical Association Journal. May 1963, 88: 943–4. PMC 1921278 . PMID 14018413.

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