5β-双氢睾酮
化合物
5β-双氢睾酮（英语：5β-Dihydrotestosterone，简称为5β-DHT，也称为5β-雄甾烷-17β-醇-3-酮，5β-androstan-17β-ol-3-one，或本胆烷-17β-醇-3-酮，etiocholan-17β-ol-3-one）是一种本胆烷类（5β-雄烷）甾体物质，和睾酮的无雄激素活性的代谢产物，由肝脏和骨髓中的5β还原酶生成[1][2]，同时也是生成3α-本胆烷二醇和3β-本胆烷二醇（分别由3α-和3β-羟基类固醇脱氢酶催化）的底物，之后再分别转化为本胆烷醇酮和表本胆烷醇酮（由17β-羟基类固醇脱氢酶催化）[3][4]。和其表观异构体5α-双氢睾酮（5α-DHT或简称DHT）不同，5β-DHT只有非常弱的结合雄激素受体的能力[1]。作为主要的睾酮代谢产物，5β-DHT的A环和B环形之间的“顺式”结构使两个环在空间上形成了一个角度，故而缺乏了雄激素活性[5]。5β-DHT和5α-DHT的另一个不同点是，5β-DHT还缺乏神经甾体活性[6][7]但其代谢产物，本胆烷醇酮却有神经甾体活性[8][9]。
| 5β-双氢睾酮 | |
|---|---|
| |
| IUPAC名 (5R,8R,9S,10S,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one | |
| 系统名 (1S,2R,7R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-5-one (1S,2R,7R,10R,11S,14S,15S)-2,15-二甲基-14-羟基四环[8.7.0.02,7.011,15]-5-十七酮 | |
| 别名 | 5β-Androstan-17β-ol-3-one; Etiocholan-17β-ol-3-one; 5β-Dihydrotestosterone; 5β-DHT |
| 识别 | |
| CAS号 | 571-22-2 |
| PubChem | 11302 |
| ChemSpider | 10827 |
| SMILES |
|
| ChEBI | 2150 |
| 性质 | |
| 化学式 | C19H30O2 |
| 摩尔质量 | 290.44 g·mol−1 |
| 若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。 | |
另见
参考文献
- ^ 1.0 1.1 Hormones, Brain and Behavior Online. Academic Press. 18 June 2002: 2262– [2019-07-15]. ISBN 978-0-08-088783-8. （原始内容存档于2018-03-27）.
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- ^ Shlomo Melmed; Kenneth S. Polonsky; P. Reed Larsen; Henry M. Kronenberg. Williams Textbook of Endocrinology. Elsevier Health Sciences. 30 November 2015: 711–. ISBN 978-0-323-29738-7.
- ^ Anita H. Payne; Matthew P. Hardy. The Leydig Cell in Health and Disease. Springer Science & Business Media. 28 October 2007: 186–. ISBN 978-1-59745-453-7.
- ^ B.A. Cooke; H.J. Van Der Molen; R.J.B. King. Hormones and their Actions. Elsevier. 1 November 1988: 173–. ISBN 978-0-08-086077-0.
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- ^ Abraham Weizman. Neuroactive Steroids in Brain Function, Behavior and Neuropsychiatric Disorders: Novel Strategies for Research and Treatment. Springer Science & Business Media. 1 February 2008: 210–. ISBN 978-1-4020-6854-6.
- ^ Li P, Bracamontes J, Katona BW, Covey DF, Steinbach JH, Akk G. Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor. Mol. Pharmacol. June 2007, 71 (6): 1582–90. PMC 3788649
. PMID 17341652. doi:10.1124/mol.106.033407.
- ^ Kaminski RM, Marini H, Kim WJ, Rogawski MA. Anticonvulsant activity of androsterone and etiocholanolone. Epilepsia. June 2005, 46 (6): 819–27. PMC 1181535 . PMID 15946323. doi:10.1111/j.1528-1167.2005.00705.x.
