17α-羟孕酮
| 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，所有数据均出自标准状态（25 ℃，100 kPa）下。 | |
17α-羟孕酮（英语：17α-Hydroxyprogesterone，17α-OHP)，有时就简称为羟孕酮（英语：hydroxyprogesterone，OHP）是一种孕酮类似的内源性的孕激素类甾体激素[1][2][3]，同时也是很多内源性甾体激素生物合成的前体，包括雄激素、雌激素、糖皮质激素和盐皮质激素以及一些神经甾体。
生物学活性
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不到皮质醇的百分之一[4][6][7]。
生物合成
.svg)
参考文献
- ^ 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.
- ^ 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.
- ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000: 532–. ISBN 978-3-88763-075-1.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
