17α-羟孕酮

化合物
(重定向自羟孕酮

17α-羟孕酮(英語:17α-Hydroxyprogesterone17α-OHP),有时就简称为羟孕酮(英語:hydroxyprogesteroneOHP)是一种孕酮类似的内源性的孕激素甾体激素[1][2][3],同时也是很多内源性甾体激素生物合成前体,包括雄激素雌激素糖皮质激素盐皮质激素以及一些神经甾体

17α-羟孕酮
IUPAC名
(8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
系统名
(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one
(1S,2R,10R,11S,14R,15S)-2,15-二甲基-14-乙酰基-14-羟基四环[8.7.0.02,7.011,15]-6-十七烯-5-酮
别名 17α-Hydroxypregn-4-ene-3,20-dione, Hydroxyprogesterone (INN)
识别
CAS号 68-96-2
PubChem 6238
ChemSpider 6002
SMILES
ChEBI 17252
IUPHAR配体 5104
性质
化学式 C21H30O3
摩尔质量 330.46 g/mol g·mol⁻¹
熔点 219.5
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

生物学活性编辑

由于和孕酮的相似性,17α-OHP是孕酮受体(PR)的一种激动剂,但相比之下比较弱[4]。另外,也是一种盐皮质激素受体(MR)的拮抗剂[5],也是糖皮质激素受体(GR)的部分激动剂,其EC50不到皮質醇的百分之一[4][6][7]


生化编辑

 
甾体激素合成路线图,17α-OHP位于孕烯一行的中左侧


参考文献编辑

  1. ^ J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014: 664–665. ISBN 978-1-4757-2085-3. 
  2. ^ I.K. Morton; Judith M. Hall. Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012: 146–. ISBN 978-94-011-4439-1. 
  3. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000: 532–. ISBN 978-3-88763-075-1. 
  4. ^ 4.0 4.1 Attardi BJ, Zeleznik A, Simhan H, Chiao JP, Mattison DR, Caritis SN. Comparison of progesterone and glucocorticoid receptor binding and stimulation of gene expression by progesterone, 17-alpha hydroxyprogesterone caproate, and related progestins. Am. J. Obstet. Gynecol. 2007, 197 (6): 599.e1–7. PMC 2278032. PMID 18060946. doi:10.1016/j.ajog.2007.05.024. 
  5. ^ Mooij CF, Parajes S, Pijnenburg-Kleizen KJ, Arlt W, Krone N, Claahsen-van der Grinten HL. Influence of 17-Hydroxyprogesterone, Progesterone and Sex Steroids on Mineralocorticoid Receptor Transactivation in Congenital Adrenal Hyperplasia. Horm Res Paediatr. April 2015. PMID 25896481. doi:10.1159/000374112. 
  6. ^ Pijnenburg-Kleizen KJ, Engels M, Mooij CF, Griffin A, Krone N, Span PN, van Herwaarden AE, Sweep FC, Claahsen-van der Grinten HL. Adrenal Steroid Metabolites Accumulating in Congenital Adrenal Hyperplasia lead to Transactivation of the Glucocorticoid Receptor. Endocrinology. 2015, 156: en20151087. PMID 26207344. doi:10.1210/en.2015-1087. 
  7. ^ Sun, Kang; Lei, Kaiyu; Chen, Li; Georgiou, Ektoras X.; Sooranna, Suren R.; Khanjani, Shirin; Brosens, Jan J.; Bennett, Phillip R.; Johnson, Mark R. Progesterone Acts via the Nuclear Glucocorticoid Receptor to Suppress IL-1β-Induced COX-2 Expression in Human Term Myometrial Cells. PLoS ONE. 2012, 7 (11): e50167. ISSN 1932-6203. PMC 3509141. PMID 23209664. doi:10.1371/journal.pone.0050167.