19-去甲睪酮

19-去甲睪酮
臨床資料
讀音	/ˈnændrəloʊn/
商品名（英語：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
懷孕分級	澳: D ; ;
給藥途徑	• Intramuscular injection (esters); • Eye drops (as NS)
藥物類別（英語：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); • Intramuscular: high
藥物代謝	Liver (reduction)
代謝產物	• 5α-Dihydronandrolone; • 19-Norandrosterone; • 19-Noretiocholanolone; • Conjugates
生物半衰期	• Nandrolone: <4.3 hours; • ND (IM): 6–12 days; • NPP: 2.7 days
作用時間	• ND (IM): 2–3 weeks; • NPP (IM): 5–7 days
排泄途徑	Urine
識別資訊
	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號	434-22-0
PubChem CID	9904;
IUPHAR/BPS	6949;
ChemSpider	9520 ;
UNII	6PG9VR430D;
ChEBI	CHEBI:7466 ;
ChEMBL	ChEMBL757 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID7023350 ;
ECHA InfoCard	100.006.457
化學資訊
化學式	C18H26O2
摩爾質量	274.404 g/mol
3D模型（JSmol（英語：JSmol））	交互式圖像;
	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 ; Key:NPAGDVCDWIYMMC-IZPLOLCNSA-N ;

19-去甲睪酮（英語：19-nortestosterone）也被稱為諾龍（Nandrolone）是一種雄激素和同化類固醇（AAS）。其酯類衍生物（如其苯丙酸酯、癸酸酯等^[2]^[10]^[6]^[11]）常作為貧血、惡病體質、骨質疏鬆症、乳癌的治療藥物^[6]，不能通過口服給藥，只能進行肌肉注射給藥^[6]^[11]。

由於19-去甲睪酮是雄激素睪酮的去甲基化類似物，因此它能作為睪酮和雙氫睪酮（DHT）的生物學靶點——雄激素受體（AR）的激動劑^[6]^[12]，在人體內引起一些雄性化症狀，如痤瘡、毛髮增長、聲音嘶啞、性慾增強等副作用^[6]。相比較而言，19-去甲睪酮的一些酯化產物蛋白同化活性較強，而雄激素活性較弱，可以作為適用於婦女兒童的較溫和藥物^[6]^[12]^[13]，以及具有緩釋作用的前體藥物^[6]。

參考文獻

^ Nandrolone Meaning in the Cambridge English Dictionary. [2019-02-15]. （原始內容存檔於2015-02-09）.
^ ^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.
^ 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.
^ Kenneth L. Becker. Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. 2001: 1185– [2019-02-15]. ISBN 978-0-7817-1750-2. （原始內容存檔於2020-05-17）.
^ ^5.0 ^5.1 ^5.2 ^5.3 ^5.4 ^5.5 ^5.6 存档副本 (PDF). [2019-02-15]. （原始內容存檔 (PDF)於2020-11-11）.
^ ^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.
^ ^7.0 ^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.
^ ^8.0 ^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.
^ 存档副本 (PDF). [2019-02-15]. （原始內容存檔 (PDF)於2019-03-09）.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000: 716–. ISBN 978-3-88763-075-1.
^ ^11.0 ^11.1 Walter Sneader. Drug Discovery: A History. John Wiley & Sons. 23 June 2005: 206–. ISBN 978-0-471-89979-2.
^ ^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.
^ Charles D. Kochakian. Anabolic-Androgenic Steroids. Springer Science & Business Media. 6 December 2012: 401– [2019-02-17]. ISBN 978-3-642-66353-6. （原始內容存檔於2019-09-09）.

延伸閱讀

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 (幫助); |issue=被忽略 (幫助)
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.

[1] Nandrolone Meaning in the Cambridge English Dictionary. [2019-02-15]. （原始內容存檔於2015-02-09）.

[Elks2014-2] 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.

[pmid10435281-3] 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.

[Becker2001-4] Kenneth L. Becker. Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. 2001: 1185– [2019-02-15]. ISBN 978-0-7817-1750-2. （原始內容存檔於2020-05-17）.

[Label-NZ-5] 5.0 ^5.1 ^5.2 ^5.3 ^5.4 ^5.5 ^5.6 存档副本 (PDF). [2019-02-15]. （原始內容存檔 (PDF)於2020-11-11）.

[Llewellyn2011-6] 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.

[Thomas2012-7] 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.

[pmid9103484-8] 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.

[Label-AU-9] 存档副本 (PDF). [2019-02-15]. （原始內容存檔 (PDF)於2019-03-09）.

[IndexNominum2000-10] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000: 716–. ISBN 978-3-88763-075-1.

[Sneader2005-11] 11.0 ^11.1 Walter Sneader. Drug Discovery: A History. John Wiley & Sons. 23 June 2005: 206–. ISBN 978-0-471-89979-2.

[pmid18500378-12] 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.

[Kochakian2012-13] Charles D. Kochakian. Anabolic-Androgenic Steroids. Springer Science & Business Media. 6 December 2012: 401– [2019-02-17]. ISBN 978-3-642-66353-6. （原始內容存檔於2019-09-09）.

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臨床資料


讀音	/ˈnændrəloʊn/^[1]
商品名（英語：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
給藥途徑	• Intramuscular injection (esters) • Eye drops (as NS)
藥物類別（英語：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]
藥物代謝	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]
識別資訊
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號	434-22-0 ^Y
PubChem CID	9904
IUPHAR/BPS	6949
ChemSpider	9520^Y
UNII	6PG9VR430D
ChEBI	CHEBI:7466^Y
ChEMBL	ChEMBL757^Y
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID7023350
ECHA InfoCard	100.006.457
化學資訊
化學式	C₁₈H₂₆O₂
摩爾質量	274.404 g/mol
3D模型（JSmol（英語：JSmol））	交互式圖像
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