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20α-Dihydroprogesterone

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20α-Dihydroprogesterone
Skeletal formula of 20α-dihydroprogesterone
Ball-and-stick model of the 20α-dihydroprogesterone molecule
Names
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
Other names
20α-DHP; 20α-Hydroxyprogesterone; 20α-OHP; 20α-Hydroxypregn-4-en-3-one; Pregn-4-en-20α-ol-3-one
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 205-649-5
MeSH 20-alpha-Dihydroprogesterone
UNII
  • InChI=1/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12-13,16-19,22H,4-11H2,1-3H3/t13-,16+,17-,18+,19+,20+,21-/m1/s1
    Key: RWBRUCCWZPSBFC-SJOKZOANBK
  • O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@H](CC[C@H]3[C@@H]1CC2)[C@H](O)C)C)(C)CC4
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

References

  1. ^ 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.
  2. ^ 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.
  3. ^ a b Cynthia L. Darlington (27 April 2009). The Female Brain. CRC Press. pp. 4–. ISBN 978-1-4200-7745-2.
  4. ^ Marianne J. Legato (29 October 2009). Principles of Gender-Specific Medicine. Academic Press. pp. 617–. ISBN 978-0-08-092150-1.
  5. ^ 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.
  6. ^ 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.



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