20α-Dihydroprogesterone
Appearance
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IUPAC name
(8S,9S,10R,13S,14S,17S)-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
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Other names
20α-DHP; 20α-Hydroxyprogesterone; 20α-OHP; 20α-Hydroxypregn-4-en-3-one; Pregn-4-en-20α-ol-3-one
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Identifiers | |
3D model (JSmol)
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EC Number |
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MeSH | 20-alpha-Dihydroprogesterone |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C21H32O2 | |
Molar mass | 316.478 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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20α-Dihydroprogesterone (20α-DHP), also known as 20α-hydroxyprogesterone (20α-OHP), is a naturally occurring, endogenous progestogen.[1][2][3] It is a metabolite of progesterone, converted by the 20α-hydroxysteroid dehydrogenases AKR1C1 and AKR1C3, and is still active as a progestogen.[4] However, it is much less potent in comparison, with about one-fifth of the progestogenic activity of progesterone.[1][2][3][5] It has been found to act as an aromatase inhibitor and to inhibit the production of estrogen in breast tissue in vitro.[6]
See also
- 20β-Dihydroprogesterone
- 17α-Hydroxyprogesterone
- 16α-Hydroxyprogesterone
- 5α-Dihydroprogesterone
- 11-Deoxycorticosterone
References
- ^ a b Beranič N, Gobec S, Rižner TL (2011). "Progestins as inhibitors of the human 20-ketosteroid reductases, AKR1C1 and AKR1C3". Chem. Biol. Interact. 191 (1–3): 227–33. doi:10.1016/j.cbi.2010.12.012. PMID 21182831.
- ^ a b Tony M. Plant; Anthony J. Zeleznik (15 November 2014). Knobil and Neill's Physiology of Reproduction: Two-Volume Set. Academic Press. pp. 1–. ISBN 978-0-12-397769-4.
- ^ a b Cynthia L. Darlington (27 April 2009). The Female Brain. CRC Press. pp. 4–. ISBN 978-1-4200-7745-2.
- ^ Marianne J. Legato (29 October 2009). Principles of Gender-Specific Medicine. Academic Press. pp. 617–. ISBN 978-0-08-092150-1.
- ^ Bertram G. Katzung (30 November 2017). Basic and Clinical Pharmacology 14th Edition. McGraw-Hill Education. p. 728. ISBN 978-1-259-64116-9.
In addition to progesterone, 20α- and 20β-hydroxyprogesterone (20α- and 20β-hydroxy-4-pregnene-3-one) also are found. These compounds have about one-fifth the progestational activity of progesterone in humans and other species.
- ^ Pasqualini JR, Chetrite G (2008). "The anti-aromatase effect of progesterone and of its natural metabolites 20alpha- and 5alpha-dihydroprogesterone in the MCF-7aro breast cancer cell line". Anticancer Res. 28 (4B): 2129–33. PMID 18751385.