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20α-Dihydrodydrogesterone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
Eliminationhalf-life14–17 hours[1]
ExcretionUrine (mainly asglucuronideconjugates)
Identifiers
  • (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
PubChemCID
ChemSpider
UNII
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)
  • [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=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

20α-Dihydrodydrogesterone (20α-DHD), also known as20α-hydroxydydrogesterone, as well as20(S)-hydroxy-9β,10α-pregna-4,6-dien-3-one, is aprogestin and the majoractive metabolite ofdydrogesterone.[2][1][3] It appears that dydrogesterone is aprodrug of 20α-DHD, as it is largelytransformed into thismetabolite when givenorally in humans.[3] 20α-DHD hasprogestogenic activity similarly to dydrogesterone, but is far lesspotent in comparison.[3]

See also

[edit]

References

[edit]
  1. ^abBińkowska M, Woroń J (June 2015)."Progestogens in menopausal hormone therapy".Przeglad Menopauzalny = Menopause Review.14 (2):134–143.doi:10.5114/pm.2015.52154.PMC 4498031.PMID 26327902.
  2. ^Olbrich M, Weigl K, Kahler E, Mihara K (October 2016). "Dydrogesterone metabolism in human liver by aldo-keto reductases and cytochrome P450 enzymes".Xenobiotica; the Fate of Foreign Compounds in Biological Systems.46 (10):868–874.doi:10.3109/00498254.2015.1134852.PMID 26796435.S2CID 22311056.
  3. ^abcRižner TL, Brožič P, Doucette C, Turek-Etienne T, Müller-Vieira U, Sonneveld E, et al. (May 2011). "Selectivity and potency of the retroprogesterone dydrogesterone in vitro".Steroids.76 (6):607–615.doi:10.1016/j.steroids.2011.02.043.PMID 21376746.S2CID 31609405.
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists

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