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]

Affinities of dydrogesterone and related steroids
ProgestogenPRARGRERα
Ki (nM)RBA (%)Ki (nM)RBA (%)Ki (nM)RBA (%)Ki (nM)
Dydrogesterone125.915.9251.210.0361.217.5>10,000
20α-Dihydrodydrogesterone125.915.93162.30.83162.32.0>10,000
Progesterone20.010025.110063.1100>10,000
Sources: See template.
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
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g/mol g·mol−1
3D model (JSmol)

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.
  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.



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