19-去甲睾酮

19-去甲睾酮（英語：19-nortestosterone）也被称为诺龙（Nandrolone）是一种雄激素和同化類固醇（AAS）。其酯类衍生物（如其苯丙酸酯、癸酸酯等^{[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	/ˈnændrəloʊn/[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	澳: D
给药途径	• Intramuscular injection (esters) • Eye drops (as NS)
藥物類別（英语：Drug class）	Androgen; Anabolic steroid; Progestogen
ATC碼	A14AB01 (WHO) S01XA11
法律規範狀態
法律規範	加：Schedule IV 英：Class C 美：附表III
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
IUPAC命名法 (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  Y
PubChem CID	9904
IUPHAR/BPS	6949
ChemSpider	9520 Y
UNII	6PG9VR430D
ChEBI	CHEBI:7466 Y
ChEMBL	ChEMBL757 Y
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID7023350
ECHA InfoCard	100.006.457
化学信息
化学式	C18H26O2
摩尔质量	274.404 g/mol
3D模型（JSmol（英语：JSmol））	交互式图像
SMILES O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4
InChI 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 Y Key:NPAGDVCDWIYMMC-IZPLOLCNSA-N Y

由于19-去甲睾酮是雄激素睾酮的去甲基化类似物，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、性欲增强等副作用^[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. 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. 存档副本 (PDF). [2019-02-15]. （原始内容存档 (PDF)于2020-11-11）.
6. William Llewellyn. Anabolics. Molecular Nutrition Llc. 2011: 402–412, 460–467, 193–194. ISBN 978-0-9828280-1-4.
7. John A. Thomas. Drugs, Athletes, and Physical Performance. Springer Science & Business Media. 6 December 2012: 27–29. ISBN 978-1-4684-5499-4.
8. 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. Walter Sneader. Drug Discovery: A History. John Wiley & Sons. 23 June 2005: 206–. ISBN 978-0-471-89979-2.
12. 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

• Geusens P. Nandrolone decanoate: pharmacological properties and therapeutic use in osteoporosis. Clin. Rheumatol. 1995,. 14 Suppl 3: 32–9. PMID 8846659. doi:10.1007/bf02210686.
• Kicman AT. Pharmacology of anabolic steroids. Br. J. Pharmacol. 2008, 154 (3): 502–21. PMC 2439524 . PMID 18500378. doi:10.1038/bjp.2008.165.
• Hemmersbach P, Grosse J. Nandrolone: a multi-faceted doping agent. Handbook of Experimental Pharmacology 195. 2010: 127–54. ISBN 978-3-540-79087-7. PMID 20020363. doi:10.1007/978-3-540-79088-4_6. |journal=被忽略 (帮助); |issue=被忽略 (帮助)
• Velema MS, Kwa BH, de Ronde W. Should androgenic anabolic steroids be considered in the treatment regime of selected chronic obstructive pulmonary disease patients?. Curr Opin Pulm Med. 2012, 18 (2): 118–24. PMID 22189453. doi:10.1097/MCP.0b013e32834e9001.
• Busardò FP, Frati P, Sanzo MD, Napoletano S, Pinchi E, Zaami S, Fineschi V. The impact of nandrolone decanoate on the central nervous system. Curr Neuropharmacol. 2015, 13 (1): 122–31. PMC 4462037 . PMID 26074747. doi:10.2174/1570159X13666141210225822.
• Wu C, Kovac JR. Novel Uses for the Anabolic Androgenic Steroids Nandrolone and Oxandrolone in the Management of Male Health. Curr Urol Rep. 2016, 17 (10): 72. PMID 27535042. doi:10.1007/s11934-016-0629-8.
• Pan MM, Kovac JR. Beyond testosterone cypionate: evidence behind the use of nandrolone in male health and wellness. Transl Androl Urol. 2016, 5 (2): 213–9. PMC 4837307 . PMID 27141449. doi:10.21037/tau.2016.03.03.