11α-羟孕酮

11α-羟孕酮（英语：11α-Hydroxyprogesterone，缩写 11α-OHP，或称为11α-羟基孕甾-4-烯-3,20-二酮，11α-hydroxypregn-4-ene-3,20-dione）是一种内源性甾体和孕酮的代谢产物^[1][2][3]，是一种弱的抗雄激素，缺乏雄激素、雌激素和孕激素活性^[4][5][6]。

11α-羟孕酮

临床资料
其他名称	11α-OHP; 11α-Hydroxypregn-4-ene-3,20-dione; 4-Pregnen-11α-ol-3,20-dione; δ4-Pregnen-11α-ol-3,20-dione
识别信息
IUPAC命名法 (8S,9S,10R,11R,13S,14S,17S)-17-acetyl-11-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one OR (1S,2R,10S,11S,14S,15S,17R)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one
CAS号	80-75-1
PubChem CID	92730
ChemSpider	83709
ChEBI	CHEBI:16076
ChEMBL	ChEMBL1563246
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID10861644
ECHA InfoCard	100.001.189
化学信息
化学式	C21H30O3
摩尔质量	330.4611 g/mol
3D模型（JSmol（英语：JSmol））	交互式图像
SMILES CC(=O)C1CCC2C1(CC(C3C2CCC4=CC(=O)CCC34C)O)C
InChI InChI=1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18+,19+,20-,21+/m0/s1 Key:BFZHCUBIASXHPK-QJSKAATBSA-N

11α-OHP也是可的松与氢化可的松化学合成的前体物质 ^[7][8][9]。

9 sources

另见

• 甘草酸

参考文献

1. Ford, Donald H. EFFECT OF 11α-HYDROXYPROGESTERONE ON REPRODUCTIVE SYSTEM OF NORMAL AND PREGNANT ADULT WISTAR RATS*. The Journal of Clinical Endocrinology & Metabolism. 1954, 14 (10): 1268–1270. ISSN 0021-972X. doi:10.1210/jcem-14-10-1268.
2. Souness GW, Latif SA, Laurenzo JL, Morris DJ. 11 alpha- and 11 beta-hydroxyprogesterone, potent inhibitors of 11 beta-hydroxysteroid dehydrogenase (isoforms 1 and 2), confer marked mineralocorticoid activity on corticosterone in the ADX rat. Endocrinology. 1995, 136 (4): 1809–12. PMID 7895695. doi:10.1210/endo.136.4.7895695.
3. Souness GW, Morris DJ. 11 alpha- and 11 beta-hydroxyprogesterone, potent inhibitors of 11 beta-hydroxysteroid dehydrogenase, possess hypertensinogenic activity in the rat. Hypertension. 1996, 27 (3 Pt 1): 421–5. PMID 8698448. doi:10.1161/01.hyp.27.3.421.
4. Lerner, Leonard J. Androgen antagonists. Pharmacology & Therapeutics B. 1975, 1 (2): 217–231. ISSN 0306-039X. doi:10.1016/0306-039X(75)90006-9. 11α Hydroxyprogesterone, while devoid of androgenic, estrogenic and progestational activity, is weakly anti androgenic in castrate rats.
5. Nguyen, Kim Thoa; Virus, Cornelia; Günnewich, Nils; Hannemann, Frank; Bernhardt, Rita. Changing the Regioselectivity of a P450 from C15 to C11 Hydroxylation of Progesterone. ChemBioChem. 2012, 13 (8): 1161–1166. ISSN 1439-4227. doi:10.1002/cbic.201100811. 11α-Hydroxyprogesterone is an important pharmaceutical compound with anti-androgenic and blood-pressure-regulating activity. [...] 11α-Hydroxyprogesterone can therefore influence blood pressure regulation.12 Furthermore, 11α-hydroxyprogesterone exhibits an anti-androgenic activity with minimal estrogenic and progestational side effects.13 This substance was also recently patented for its role in treating skin diseases, especially for psoriasis in combination with clobetasol propionate and minoxidil.14.
6. Tindall, D.J.; Chang, C.H.; Lobl, T.J.; Cunningham, G.R. Androgen antagonists in androgen target tissues. Pharmacology & Therapeutics. 1984, 24 (3): 367–400. ISSN 0163-7258. doi:10.1016/0163-7258(84)90010-X.
7. Peter J. Dunn; Andrew Wells; Michael T. Williams. Green Chemistry in the Pharmaceutical Industry. John Wiley & Sons. 2 February 2010: 2–. ISBN 978-3-527-62969-5.
8. Clemens Lamberth; Jürgen Dinges. Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals. Wiley. 17 May 2016: 250–. ISBN 978-3-527-69396-2.
9. Kishan Gopal Ramawat; Jean-Michel Mérillon. Bioactive Molecules and Medicinal Plants. Springer Science & Business Media. 16 October 2008: 5–. ISBN 978-3-540-74603-4.