11α-羥孕酮

11α-羥孕酮
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
識別資訊
	IUPAC命名法 (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號	80-75-1
PubChem CID	92730;
ChemSpider	83709;
ChEBI	CHEBI:16076;
ChEMBL	ChEMBL1563246;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID10861644 ;
ECHA InfoCard	100.001.189
化學資訊
化學式	C21H30O3
摩爾質量	330.4611 g/mol
3D模型（JSmol（英語：JSmol））	交互式圖像;
	SMILES CC(=O)C1CCC2C1(CC(C3C2CCC4=CC(=O)CCC34C)O)C;
	InChI 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-羥孕酮（英語：11α-Hydroxyprogesterone，縮寫 11α-OHP，或稱為11α-羥基孕甾-4-烯-3,20-二酮，11α-hydroxypregn-4-ene-3,20-dione）是一種內源性甾體和孕酮的代謝產物^[1]^[2]^[3]，是一種弱的抗雄激素，缺乏雄激素、雌激素和孕激素活性^[4]^[5]^[6]。

11α-OHP也是可的松與氫化可的松化學合成的前體物質 ^[7]^[8]^[9]。

另見

甘草酸

參考文獻

^ Ford, Donald H. EFFECT OF 11α-HYDROXYPROGESTERONE ON REPRODUCTIVE SYSTEM OF NORMAL AND PREGNANT ADULT WISTAR RATS*. The Journal of Clinical Endocrinology & Metabolism. 1954, 14 (10): 1268–1270. ISSN 0021-972X. doi:10.1210/jcem-14-10-1268.
^ 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.
^ Tindall, D.J.; Chang, C.H.; Lobl, T.J.; Cunningham, G.R. Androgen antagonists in androgen target tissues. Pharmacology & Therapeutics. 1984, 24 (3): 367–400. ISSN 0163-7258. doi:10.1016/0163-7258(84)90010-X.
^ Peter J. Dunn; Andrew Wells; Michael T. Williams. Green Chemistry in the Pharmaceutical Industry. John Wiley & Sons. 2 February 2010: 2–. ISBN 978-3-527-62969-5.
^ Clemens Lamberth; Jürgen Dinges. Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals. Wiley. 17 May 2016: 250–. ISBN 978-3-527-69396-2.
^ Kishan Gopal Ramawat; Jean-Michel Mérillon. Bioactive Molecules and Medicinal Plants. Springer Science & Business Media. 16 October 2008: 5–. ISBN 978-3-540-74603-4.

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[Ford1954-1] Ford, Donald H. EFFECT OF 11α-HYDROXYPROGESTERONE ON REPRODUCTIVE SYSTEM OF NORMAL AND PREGNANT ADULT WISTAR RATS*. The Journal of Clinical Endocrinology & Metabolism. 1954, 14 (10): 1268–1270. ISSN 0021-972X. doi:10.1210/jcem-14-10-1268.

[pmid7895695-2] 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.

[pmid8698448-3] 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.

[Lerner1975-4] 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.

[NguyenVirus2012-5] 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.

[TindallChang1984-6] Tindall, D.J.; Chang, C.H.; Lobl, T.J.; Cunningham, G.R. Androgen antagonists in androgen target tissues. Pharmacology & Therapeutics. 1984, 24 (3): 367–400. ISSN 0163-7258. doi:10.1016/0163-7258(84)90010-X.

[DunnWells2010-7] Peter J. Dunn; Andrew Wells; Michael T. Williams. Green Chemistry in the Pharmaceutical Industry. John Wiley & Sons. 2 February 2010: 2–. ISBN 978-3-527-62969-5.

[LamberthDinges2016-8] Clemens Lamberth; Jürgen Dinges. Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals. Wiley. 17 May 2016: 250–. ISBN 978-3-527-69396-2.

[RamawatMérillon2008-9] Kishan Gopal Ramawat; Jean-Michel Mérillon. Bioactive Molecules and Medicinal Plants. Springer Science & Business Media. 16 October 2008: 5–. ISBN 978-3-540-74603-4.

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