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]。
Quick Facts 临床资料, 其他名称 ...
11α-羟孕酮 |
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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 |
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(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
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CAS号 | 80-75-1 |
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PubChem CID | |
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ChemSpider | |
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ChEBI | |
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ChEMBL | |
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CompTox Dashboard (EPA) | |
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ECHA InfoCard | 100.001.189 |
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化学式 | C21H30O3 |
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摩尔质量 | 330.4611 g/mol |
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3D模型(JSmol) | |
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CC(=O)C1CCC2C1(CC(C3C2CCC4=CC(=O)CCC34C)O)C
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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
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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]。
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.
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.
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.
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.