11α-羟孕酮

11α-羟孕酮（英語：，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
臨床資料
其他名稱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
  • (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
ChemSpider
ChEBI
ChEMBL
ECHA InfoCard100.001.189
化学
化学式C21H30O3
摩尔质量330.4611 g/mol
3D模型（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-OHP也是可的松与氢化可的松化学合成的前体物质 [7][8][9]。

另见

参考文献
  1. Ford, Donald H. . 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. . Endocrinology. 1995, 136 (4): 1809–12. PMID 7895695. doi:10.1210/endo.136.4.7895695.
  3. Souness GW, Morris DJ. . Hypertension. 1996, 27 (3 Pt 1): 421–5. PMID 8698448. doi:10.1161/01.hyp.27.3.421.
  4. Lerner, Leonard J. . 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. . 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. . 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. . John Wiley & Sons. 2 February 2010: 2–. ISBN 978-3-527-62969-5.
  8. Clemens Lamberth; Jürgen Dinges. . Wiley. 17 May 2016: 250–. ISBN 978-3-527-69396-2.
  9. Kishan Gopal Ramawat; Jean-Michel Mérillon. . Springer Science & Business Media. 16 October 2008: 5–. ISBN 978-3-540-74603-4.
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