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| Other names | 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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| ECHA InfoCard | 100.001.189 |
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| Formula | C21H30O3 |
| Molar mass | 330.468 g·mol−1 |
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11α-Hydroxyprogesterone (11α-OHP), or11α-hydroxypregn-4-ene-3,20-dione is anendogenoussteroid andmetabolite ofprogesterone.[1][2][3] It is a weakantiandrogen, and is devoid ofandrogenic,estrogenic, andprogestogenic activity.[4][5][6]
11α-OHP was investigated as atopical antiandrogen for the treatment ofandrogen-dependentskin conditions in the early 1950s, and was found to produce some benefit.[7] In 1995, 11α-OHP, along with itsepimer11β-hydroxyprogesterone, was identified as a very potentcompetitiveinhibitor of bothisoforms (1 and2) of11β-hydroxysteroid dehydrogenase (11β-HSD).[2][3] It is notably not metabolized by 11β-HSD2.[8]
11α-OHP is a more potent inhibitor of 11β-HSD thanenoxolone (glycyrrhetinic acid) orcarbenoxolonein vitro (IC50 = 0.9 nM; IC50 = 5 nM in transfected cells).[8][9][10] The compound has been found to be highly active in conferringmineralocorticoidsodium-retaining activity ofcorticosteronein vivo in ratbioassays and in increasingblood pressure, effects that it mediates by preventing the 11β-HSD-mediated inactivation of endogenouscorticosteroids.[2][3]
11α-OHP is used as aprecursor inchemical syntheses ofcortisone andhydrocortisone.[11][12][13]
11α Hydroxyprogesterone, while devoid of androgenic, estrogenic and progestational activity, is weakly anti androgenic in castrate rats.
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 has been proposed for treating skin diseases, especially for psoriasis in combination with clobetasol propionate and minoxidil.14.
Topical antiandrogens have also been tried, including topical progesterone, which proved ineffective. However, small studies with topical 11α-hydroxyprogesterone and 17α-estradiol showed some benefit [38,39].
11 alpha-Hydroxyprogesterone (11 alpha OH-P) was an order of magnitude more potent a competitive inhibitor of the 11 beta HSD-2 than was glycyrrhetinic acid (GA) (approximate IC50 = 0.9 vs. 15 nM).
In intact cells 11α-hydroxyprogesterone is a more potent inhibitor of 11β-HSD1 than glycyrrhetinic acid or 11β-hydroxyprogesterone (117, 118).
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