5β-双氢睾酮

化合物

5β-双氢睾酮(英語: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,由肝脏骨髓中的5β还原酶生成[1][2],同时也是生成3α-本胆烷二醇3β-本胆烷二醇(分别由3α-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
 
  • C[C@]12CCC(=O)C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C
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. ^ 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). 
  2. ^ H.-J. Bandmann; R. Breit; E. Perwein. Klinefelter's Syndrome. Springer Science & Business Media. 6 December 2012: 293– [2019-07-15]. ISBN 978-3-642-69644-2. (原始内容存档于2018-12-02). 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ Current Topics in Membranes and Transport. Academic Press. 1 February 1988: 169– [2019-07-15]. ISBN 978-0-08-058502-4. (原始内容存档于2018-12-20). 
  7. ^ 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. 
  8. ^ 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. 
  9. ^ 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.