11α-Hydroxyprogesterone

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Not to be confused with
17α-hydroxyprogesterone
.
11α-Hydroxyprogesterone
Clinical data
Other names11α-OHP; 11α-Hydroxypregn-4-ene-3,20-dione; 4-Pregnen-11α-ol-3,20-dione; δ4-Pregnen-11α-ol-3,20-dione
Identifiers
  • (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
JSmol)
  • CC(=O)C1CCC2C1(CC(C3C2CCC4=CC(=O)CCC34C)O)C
  • 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-Hydroxyprogesterone (11α-OHP), or 11α-hydroxypregn-4-ene-3,20-dione is an

endogenous steroid and metabolite of progesterone.[1][2][3] It is a weak antiandrogen, and is devoid of androgenic, estrogenic, and progestogenic activity.[4][5][6]

11α-OHP was investigated as a

11β-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 than enoxolone (glycyrrhetinic acid) or carbenoxolone in vitro (IC50 = 0.9 nM; IC50 = 5 nM in transfected cells).[8][9][10] 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.[2][3]

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.[5]

11α-OHP is used as a precursor in chemical syntheses of cortisone and hydrocortisone.[11][12][13]

See also

References

  1. PMID 13201630
    .
  2. ^
    PMID 7895695
    .
  3. ^
    PMID 8698448
    .
  4. PMID 772705
    . 11α Hydroxyprogesterone, while devoid of androgenic, estrogenic and progestational activity, is weakly anti androgenic in castrate rats.
  5. ^
    S2CID 34483686
    . 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. PMID 6205409
    .
  7. ISBN 978-0-203-90831-0
    . 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].
  8. ^
    PMID 8641180
    . 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).
  9. PMID 15466942
    . In intact cells 11α-hydroxyprogesterone is a more potent inhibitor of 11β-HSD1 than glycyrrhetinic acid or 11β-hydroxyprogesterone (117, 118).
  10. S2CID 22551136
    .
  11. ISBN 978-3-527-62969-5
    .
  12. ISBN 978-3-527-69396-2
    .
  13. ISBN 978-3-540-74603-4
    .
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