20α-Dihydrodydrogesterone

20α-Dihydrodydrogesterone (20α-DHD), also known as 20α-hydroxydydrogesterone, as well as 20(S)-hydroxy-9β,10α-pregna-4,6-dien-3-one, is a progestin and the major active metabolite of dydrogesterone.[2][1][3] It appears that dydrogesterone is a prodrug of 20α-DHD, as it is largely transformed into this metabolite when given orally in humans.[3] 20α-DHD has progestogenic activity similarly to dydrogesterone, but is far less potent in comparison.[3]

20α-Dihydrodydrogesterone
Clinical data
Other names20α-DHD; 20α-Hydroxydydrogesterone; 20(S)-Hydroxy-9β,10α-pregna-4,6-dien-3-one
Drug classProgestin; Progestogen
Pharmacokinetic data
Elimination half-life14–17 hours[1]
ExcretionUrine (mainly as glucuronide conjugates)
Identifiers
IUPAC name
  • (8S,9R,10S,13S,14S,17S)-17-(1-Hydroxyethyl)-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)
SMILES
  • [H][C@@]1(CC[C@@]2([H])[C@]3([H])C=CC4=CC(=O)CC[C@]4(C)[C@]3([H])CC[C@]12C)[C@H](C)O
InChI
  • InChI=1/C21H30O2/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/h4-5,12-13,16-19,22H,6-11H2,1-3H3/t13-,16-,17+,18-,19+,20-,21+/s2
  • Key:IQPNZLYVKOVQGH-AIANXXHJNA-N

See also

References
  1. Bińkowska, Małgorzata; Woroń, Jarosław (2015). "Progestogens in menopausal hormone therapy". Menopausal Review. 14 (2): 134–143. doi:10.5114/pm.2015.52154. ISSN 1643-8876. PMC 4498031. PMID 26327902.
  2. Olbrich, Matthias; Weigl, Kevin; Kahler, Elke; Mihara, Katsuhiro (2016). "Dydrogesterone metabolism in human liver by aldo-keto reductases and cytochrome P450 enzymes". Xenobiotica. 46 (10): 868–874. doi:10.3109/00498254.2015.1134852. ISSN 0049-8254. PMID 26796435. S2CID 22311056.
  3. Rižner TL, Brožič P, Doucette C, Turek-Etienne T, Müller-Vieira U, Sonneveld E, van der Burg B, Böcker C, Husen B (May 2011). "Selectivity and potency of the retroprogesterone dydrogesterone in vitro". Steroids. 76 (6): 607–15. doi:10.1016/j.steroids.2011.02.043. PMID 21376746. S2CID 31609405.



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