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化合物简介
11α-Hydroxyprogesterone (11α-OHP), or 11α-hydroxypregn-4-ene-3,20-dione is an endogenous steroid and metabolite of progesterone. It is a weak antiandrogen, and is devoid of androgenic, estrogenic, and progestogenic activity. It was investigated as a topical antiandrogen for the treatment of androgen-dependent skin conditions in the early 1950s, and was found to produce some benefit. In 1995, 11α-OHP, along with its analogue 11β-hydroxyprogesterone, was identified as a very potent competitive inhibitor of both isoforms (1 and 2) of 11β-hydroxysteroid dehydrogenase (11β-HSD). It is notably not metabolized by 11β-HSD2. 11α-OHP is a more potent inhibitor of 11β-HSD than enoxolone (glycyrrhetinic acid) or carbenoxolone in vitro (IC50 = 0.9 nM; IC50 = 5 nM in transfected cells). The compound has been found to be highly active in conferring mineralocorticoid sodium-retaining activity of corticosterone in vivo in rat bioassays and in increasing blood pressure, effects that it mediates by preventing the 11β-HSD-mediated inactivation of endogenous corticosteroids. Because of its inhibition of 11β-HSD and consequent potentiation of corticosteroids, 11α-OHP has recently been patented for the treatment of skin diseases, particularly psoriasis in combination with clobetasol propionate and minoxidil.
基本信息
CAS:80-75-1
中文别名:11alpha-羟基黄体酮;11Α-羟孕酮;11ALPHA-孕酮;
英文别名:11alpha-hydroxyprogesterone;Pregn-4-ene-3,20-dione, 11-hydroxy-, (11α)-;HYDROXYPROGESTERONE,11A;DG 322B;11A-HYDROXYPROGESTERONE;4-PREGNEN-11A-OL-3,20-DIONE;Progesterone,11alpha-hydroxy;Progesterone, 11.α.-hydroxy-;11ALPHA-HYDROXYPROGESTERONE;U 0384;
分子式:C21H30O3
分子量:330.461
精确质量:330.219
Psa:54.37
Logp:3.6943
中文别名:11alpha-羟基黄体酮;11Α-羟孕酮;11ALPHA-孕酮;
英文别名:11alpha-hydroxyprogesterone;Pregn-4-ene-3,20-dione, 11-hydroxy-, (11α)-;HYDROXYPROGESTERONE,11A;DG 322B;11A-HYDROXYPROGESTERONE;4-PREGNEN-11A-OL-3,20-DIONE;Progesterone,11alpha-hydroxy;Progesterone, 11.α.-hydroxy-;11ALPHA-HYDROXYPROGESTERONE;U 0384;
分子式:C21H30O3
分子量:330.461
精确质量:330.219
Psa:54.37
Logp:3.6943
编号系统
EINECS号:201-306-9
物化性质
外观与性状:白色至淡米色结晶粉末
密度:1.15 g/cm3
沸点:487.4ºC at 760 mmHg
熔点:165-166ºC(lit.)
闪点:262.7ºC
折射率:1.557
储存条件:Refrigerator
密度:1.15 g/cm3
沸点:487.4ºC at 760 mmHg
熔点:165-166ºC(lit.)
闪点:262.7ºC
折射率:1.557
储存条件:Refrigerator
安全信息
安全说明:S24/25
生产方法及用途
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上游原料
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图谱
13C NMR : Predict

1H NMR : Predict

Mass spectrum (electron ionization)
