19-去甲睾酮

19-去甲睾酮(英語:19-nortestosterone)也被称为诺龙(Nandrolone)是一种雄激素同化類固醇(AAS)。其酯类衍生物(如其苯丙酸酯癸酸酯[9][10][6][11])常作为贫血惡病體質骨質疏鬆症乳癌的治疗药物[6],不能通过口服给药,只能进行肌肉注射给药[6][11]

19-去甲睾酮
Nandrolone Structural Formula V1.svg
Nandrolone molecule ball.png
系统(IUPAC)命名名称
(8R,9S,10R,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
临床数据
读音/ˈnændrəln/[1]
商品名• Deca-Durabolin (as ND)
• Durabolin (as NPP)
• Many others (see here)
妊娠分级
  • AU: D
  • US: X (禁忌)
给药途径Intramuscular injection (esters)
Eye drops (as NS)
合法狀態
合法状态
药代动力学数据
生物利用度Oral: <3% (pigs)[2]
Intramuscular: high[3]
代谢Liver (reduction)[4][5]
代謝產物5α-Dihydronandrolone[4][6]
19-Norandrosterone[4]
19-Noretiocholanolone[4]
Conjugates[5]
生物半衰期• Nandrolone: <4.3 hours[4]
ND (IM): 6–12 days[4][6][7]
NPP: 2.7 days[7]
作用时间ND (IM): 2–3 weeks[6][8]
NPP (IM): 5–7 days[6][7]
排泄Urine[4]
识别信息
CAS注册号434-22-0  ✓
ATC代码A14AB01 S01XA11
PubChemCID 9904
IUPHAR/BPS英语IUPHAR/BPS6949
ChemSpider9520 ✓
UNII6PG9VR430D ✓
ChEBICHEBI:7466 ✓
ChEMBL英语ChEMBLCHEMBL757 ✓
其他名称• 19-Nortestosterone
• 10-Nortestosterone
• Estr-4-en-17β-ol-3-one
• Estrenolone / Oestrenolone
19-Norandrost-4-en-17β-ol-3-one
• Norandrostenolone
• Nortestrionate / Nortestonate
• SG-4341[9]
化学信息
化学式C18H26O2
摩尔质量274.404 g/mol

由于19-去甲睾酮是雄激素睾酮去甲基化类似物,因此它能作为睾酮和双氢睾酮(DHT)的生物学靶点——雄激素受体(AR)的激动剂[6][12],在人体内引起一些雄性化症狀,如痤疮毛发增长、声音嘶哑、性欲增强副作用[6]。相比较而言,19-去甲睾酮的一些酯化产物蛋白同化活性较强,而雄激素活性较弱,可以作为适用于妇女儿童的较温和药物[6][12][13],以及具有缓释作用的前体药物[6]

参考文献编辑

  1. ^ Nandrolone Meaning in the Cambridge English Dictionary. 
  2. ^ McEvoy JD, McVeigh CE, McCaughey WJ. Residues of nortestosterone esters at injection sites. Part 1. Oral bioavailability. Analyst. 1998, 123 (12): 2475–8. PMID 10435281. doi:10.1039/a804919j. 
  3. ^ Kenneth L. Becker. Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. 2001: 1185–. ISBN 978-0-7817-1750-2. 
  4. ^ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 http://www.medsafe.govt.nz/profs/Datasheet/d/Decadurabolininj.pdf
  5. ^ 5.0 5.1 John A. Thomas. Drugs, Athletes, and Physical Performance. Springer Science & Business Media. 6 December 2012: 27–29. ISBN 978-1-4684-5499-4. 
  6. ^ 6.00 6.01 6.02 6.03 6.04 6.05 6.06 6.07 6.08 6.09 6.10 William Llewellyn. Anabolics. Molecular Nutrition Llc. 2011: 402–412, 460–467, 193–194. ISBN 978-0-9828280-1-4. 
  7. ^ 7.0 7.1 7.2 Minto CF, Howe C, Wishart S, Conway AJ, Handelsman DJ. Pharmacokinetics and pharmacodynamics of nandrolone esters in oil vehicle: effects of ester, injection site and injection volume. J. Pharmacol. Exp. Ther. 1997, 281 (1): 93–102. PMID 9103484. 
  8. ^ 存档副本 (PDF). [2019-02-15]. (原始内容存档 (PDF)于2019-03-09). 
  9. ^ 9.0 9.1 J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014: 660–. ISBN 978-1-4757-2085-3. 
  10. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000: 716–. ISBN 978-3-88763-075-1. 
  11. ^ 11.0 11.1 Walter Sneader. Drug Discovery: A History. John Wiley & Sons. 23 June 2005: 206–. ISBN 978-0-471-89979-2. 
  12. ^ 12.0 12.1 Kicman AT. Pharmacology of anabolic steroids. Br. J. Pharmacol. 2008, 154 (3): 502–21. PMC 2439524. PMID 18500378. doi:10.1038/bjp.2008.165. 
  13. ^ Charles D. Kochakian. Anabolic-Androgenic Steroids. Springer Science & Business Media. 6 December 2012: 401– [2019-02-17]. ISBN 978-3-642-66353-6. (原始内容存档于2019-09-09). 

延伸阅读编辑