19-去甲睾酮

(重定向自诺龙

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[2][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
臨床資料
读音/ˈnændrəln/[1]
商品名英语Drug nomenclature• Deca-Durabolin (as ND)
• Durabolin (as NPP)
• Many others (see here)
其他名稱• 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[2]
懷孕分級
  • : D
给药途径Intramuscular injection (esters)
Eye drops (as NS)
藥物類別英语Drug classAndrogen; Anabolic steroid; Progestogen
ATC碼
法律規範狀態
法律規範
藥物動力學數據
生物利用度Oral: <3% (pigs)[3]
Intramuscular: high[4]
药物代谢Liver (reduction)[5][7]
代謝產物5α-Dihydronandrolone[5][6]
19-Norandrosterone[5]
19-Noretiocholanolone[5]
Conjugates[7]
生物半衰期• Nandrolone: <4.3 hours[5]
ND (IM): 6–12 days[5][6][8]
NPP: 2.7 days[8]
作用時間ND (IM): 2–3 weeks[6][9]
NPP (IM): 5–7 days[6][8]
排泄途徑Urine[5]
识别信息
  • (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
CAS号434-22-0  checkY
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard英语CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.006.457 編輯維基數據鏈接
化学信息
化学式C18H26O2
摩尔质量274.404 g/mol
3D模型(JSmol英语JSmol
  • O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4
  • InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1 checkY
  • Key:NPAGDVCDWIYMMC-IZPLOLCNSA-N checkY

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

  1. ^ Nandrolone Meaning in the Cambridge English Dictionary. [2019-02-15]. (原始内容存档于2015-02-09). 
  2. ^ 2.0 2.1 J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014: 660–. ISBN 978-1-4757-2085-3. 
  3. ^ 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. 
  4. ^ Kenneth L. Becker. Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. 2001: 1185– [2019-02-15]. ISBN 978-0-7817-1750-2. (原始内容存档于2020-05-17). 
  5. ^ 5.0 5.1 5.2 5.3 5.4 5.5 5.6 存档副本 (PDF). [2019-02-15]. (原始内容存档 (PDF)于2020-11-11). 
  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 John A. Thomas. Drugs, Athletes, and Physical Performance. Springer Science & Business Media. 6 December 2012: 27–29. ISBN 978-1-4684-5499-4. 
  8. ^ 8.0 8.1 8.2 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. 
  9. ^ 存档副本 (PDF). [2019-02-15]. (原始内容存档 (PDF)于2019-03-09). 
  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). 

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