19-去甲睾酮

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
  • A14AB01 (WHO) S01XA11
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
  • 9904
IUPHAR/BPS
  • 6949
ChemSpider
  • 9520 checkY
UNII
  • 6PG9VR430D
ChEBI
  • CHEBI:7466 checkY
ChEMBL
  • ChEMBL757 checkY
CompTox Dashboard英语CompTox Chemicals Dashboard (EPA)
  • DTXSID7023350 編輯維基數據鏈接
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
  • 交互式图像
  • 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

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]

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可免费查阅. 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可免费查阅. 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可免费查阅. 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可免费查阅. PMID 27141449. doi:10.21037/tau.2016.03.03. 
受体
AR (A, B)

注意:此处包括了那些只有微弱男性化效应(或抗男性化(如氧雄龙))的蛋白同化甾类(因为它们合成代谢效应也是通过激活雄激素受体而是显得)。

  • Mixed (SARMs): AC-262,356
  • Andarine
  • BMS-564,929
  • Enobosarm
  • LGD-2226
  • LGD-3303
  • S-23
  • S-40503

(抑制剂)
  • 22-ABC
  • 3,3′-Dimethoxybenzidine
  • 3-Methoxybenzidine
  • Aminoglutethimide
  • Cyanoketone
  • Danazol
  • Etomidate
  • Mitotane
  • Trilostane
17α-羟化酶,
17,20-裂合酶
3β-HSD (I, II)
17β-HSD (I-XIV)
  • Danazol
  • Simvastatin
5α還原酶 (I, II)
  • 22-Oxime
  • Alfatradiol
  • Azelaic acid
  • β-Sitosterol
  • Bexlosteride
  • Dutasteride
  • 表睾酮
  • Epristeride
  • Finasteride
  • Izonsteride
  • L-39
  • Lapisteride
  • Polyunsaturated fatty acids (α-linolenic acid, linoleic acid, γ-linolenic acid, oleic acid)
  • Turosteride
  • Vitamin B6
  • 1,4,6-Androstatriene-3,17-dione
  • 4-Androstene-3,6,17-trione
  • 4-Cyclohexylaniline
  • 4-Hydroxytestosterone
  • 5α-DHNET
  • Abyssinone II
  • Aminoglutethimide
  • Anastrozole
  • 抗坏血酸维生素C
  • Atamestane
  • Bifonazole
  • CGP-45,688
  • CGS-47,645
  • Clotrimazole
  • 双氢睾酮
  • Difeconazole
  • Econazole
  • Exemestane
  • Fadrozole
  • Fenarimol
  • Finrozole
  • Formestane
  • Imazalil
  • Isoconazole
  • Ketoconazole
  • Letrozole
  • Liarozole
  • MEN-11066
  • Miconazole
  • Minamestane
  • Nimorazole
  • NKS01
  • ORG-33,201
  • Penconazole
  • Plomestane
  • Prochloraz
  • Propioconazole
  • Pyridoglutethimide
  • Rogletimide
  • Rotenone
  • Talarozole
  • Testolactone
  • Tioconazole
  • Triadimefon
  • Triadimenol
  • Troglitazone
  • Vorozole
  • YM511

Note: 21-Hydroxylase inhibitors may also affect androgen levels as they prevent metabolism of androgen steroid precursors.

其他
间接
  • Estrogens/Antiestrogens (see here)
  • GnRH agonists/antagonists (see here)
  • Gonadotropins/Antigonadotropins (see here)
  • Plasma proteins (SHBG, ABP, Albumin)
  • Progestogens/Antiprogestins (see here)
  • Prolactin