17α-羟孕酮

17α-羟孕酮
	IUPAC名; (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
	系统名; (1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one; (1S,2R,10R,11S,14R,15S)-2,15-二甲基-14-乙酰基-14-羟基四环[8.7.0.02,7.011,15]-6-十七烯-5-酮
别名	17α-Hydroxypregn-4-ene-3,20-dione, Hydroxyprogesterone (INN)
识别
CAS号	68-96-2
PubChem	6238
ChemSpider	6002
SMILES	CC(=O)C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O;
ChEBI	17252
IUPHAR配体	5104
性质
化学式	C21H30O3
摩尔质量	330.46 g/mol g·mol⁻¹
熔点	219.5
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

17α-羟孕酮（英语：17α-Hydroxyprogesterone，17α-OHP)，有时就简称为羟孕酮（英语：hydroxyprogesterone，OHP）是一种孕酮类似的内源性的孕激素类甾体激素^[1]^[2]^[3]，同时也是很多内源性甾体激素生物合成的前体，包括雄激素、雌激素、糖皮质激素和盐皮质激素以及一些神经甾体。

生物学活性

由于和孕酮的相似性，17α-OHP是孕酮受体（PR）的一种激动剂，但相比之下比较弱^[4]。另外，也是一种盐皮质激素受体（MR）的拮抗剂^[5]，也是糖皮质激素受体（GR）的部分激动剂，其EC₅₀不到皮质醇的百分之一^[4]^[6]^[7]。

生物合成

甾体激素合成路线图，17α-OHP位于孕烯一行的中左侧

参考文献

^ J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014: 664–665. ISBN 978-1-4757-2085-3.
^ I.K. Morton; Judith M. Hall. Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012: 146–. ISBN 978-94-011-4439-1.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000: 532–. ISBN 978-3-88763-075-1.
^ ^4.0 ^4.1 Attardi BJ, Zeleznik A, Simhan H, Chiao JP, Mattison DR, Caritis SN. Comparison of progesterone and glucocorticoid receptor binding and stimulation of gene expression by progesterone, 17-alpha hydroxyprogesterone caproate, and related progestins. Am. J. Obstet. Gynecol. 2007, 197 (6): 599.e1–7. PMC 2278032  . PMID 18060946. doi:10.1016/j.ajog.2007.05.024.
^ Mooij CF, Parajes S, Pijnenburg-Kleizen KJ, Arlt W, Krone N, Claahsen-van der Grinten HL. Influence of 17-Hydroxyprogesterone, Progesterone and Sex Steroids on Mineralocorticoid Receptor Transactivation in Congenital Adrenal Hyperplasia. Horm Res Paediatr. April 2015. PMID 25896481. doi:10.1159/000374112.
^ Pijnenburg-Kleizen KJ, Engels M, Mooij CF, Griffin A, Krone N, Span PN, van Herwaarden AE, Sweep FC, Claahsen-van der Grinten HL. Adrenal Steroid Metabolites Accumulating in Congenital Adrenal Hyperplasia lead to Transactivation of the Glucocorticoid Receptor. Endocrinology. 2015, 156: en20151087. PMID 26207344. doi:10.1210/en.2015-1087.
^ Sun, Kang; Lei, Kaiyu; Chen, Li; Georgiou, Ektoras X.; Sooranna, Suren R.; Khanjani, Shirin; Brosens, Jan J.; Bennett, Phillip R.; Johnson, Mark R. Progesterone Acts via the Nuclear Glucocorticoid Receptor to Suppress IL-1β-Induced COX-2 Expression in Human Term Myometrial Cells. PLoS ONE. 2012, 7 (11): e50167. ISSN 1932-6203. PMC 3509141  . PMID 23209664. doi:10.1371/journal.pone.0050167.

[Elks2014-1] J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014: 664–665. ISBN 978-1-4757-2085-3.

[MortonHall2012-2] I.K. Morton; Judith M. Hall. Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012: 146–. ISBN 978-94-011-4439-1.

[IndexNominum2000-3] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000: 532–. ISBN 978-3-88763-075-1.

[pmid18060946-4] 4.0 ^4.1 Attardi BJ, Zeleznik A, Simhan H, Chiao JP, Mattison DR, Caritis SN. Comparison of progesterone and glucocorticoid receptor binding and stimulation of gene expression by progesterone, 17-alpha hydroxyprogesterone caproate, and related progestins. Am. J. Obstet. Gynecol. 2007, 197 (6): 599.e1–7. PMC 2278032  . PMID 18060946. doi:10.1016/j.ajog.2007.05.024.

[pmid25896481-5] Mooij CF, Parajes S, Pijnenburg-Kleizen KJ, Arlt W, Krone N, Claahsen-van der Grinten HL. Influence of 17-Hydroxyprogesterone, Progesterone and Sex Steroids on Mineralocorticoid Receptor Transactivation in Congenital Adrenal Hyperplasia. Horm Res Paediatr. April 2015. PMID 25896481. doi:10.1159/000374112.

[pmid26207344-6] Pijnenburg-Kleizen KJ, Engels M, Mooij CF, Griffin A, Krone N, Span PN, van Herwaarden AE, Sweep FC, Claahsen-van der Grinten HL. Adrenal Steroid Metabolites Accumulating in Congenital Adrenal Hyperplasia lead to Transactivation of the Glucocorticoid Receptor. Endocrinology. 2015, 156: en20151087. PMID 26207344. doi:10.1210/en.2015-1087.

[SunLei2012-7] Sun, Kang; Lei, Kaiyu; Chen, Li; Georgiou, Ektoras X.; Sooranna, Suren R.; Khanjani, Shirin; Brosens, Jan J.; Bennett, Phillip R.; Johnson, Mark R. Progesterone Acts via the Nuclear Glucocorticoid Receptor to Suppress IL-1β-Induced COX-2 Expression in Human Term Myometrial Cells. PLoS ONE. 2012, 7 (11): e50167. ISSN 1932-6203. PMC 3509141  . PMID 23209664. doi:10.1371/journal.pone.0050167.

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17α-羟孕酮


IUPAC名 (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
系统名 (1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,7.0^11,15]heptadec-6-en-5-one (1S,2R,10R,11S,14R,15S)-2,15-二甲基-14-乙酰基-14-羟基四环[8.7.0.0^2,7.0^11,15]-6-十七烯-5-酮
别名	17α-Hydroxypregn-4-ene-3,20-dione, Hydroxyprogesterone (INN)
识别
CAS号	68-96-2
PubChem	6238
ChemSpider	6002
SMILES	CC(=O)C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O
ChEBI	17252
IUPHAR配体	5104
性质
化学式	C₂₁H₃₀O₃
摩尔质量	330.46 g/mol g·mol⁻¹
熔点	219.5
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。