Jump to content

20α-Dihydroprogesterone

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Vanished user 0x8cSXE0x6 (talk | contribs) at 19:42, 6 November 2016. The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

20α-Dihydroprogesterone
Skeletal formula of 20α-dihydroprogesterone
Ball-and-stick model of the 20α-dihydroprogesterone molecule
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).
checkY verify (what is checkY☒N ?)

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 although still active as a progestogen,[4] is much less potent in comparison.[1][2][3] It has been found to act as an aromatase inhibitor and to inhibit the production of estrogen in breast tissue in vitro.[5]

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. ^ 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.


Template:Steroid hormone metabolism modulators