20α-Dihydrotrengestone

20α-Dihydrotrengestone (20α-DHTG), also known as 20α-hydroxytrengestone, as well as 6-chloro-20(S)-hydroxy-9β,10α-pregna-1,4,6-trien-3-one, is a progestin and the major active metabolite of trengestone.[1][2] It appears that trengestone is a prodrug of 20α-DHTG, as it is largely transformed into this metabolite when given orally in humans.[2][1] 20α-DHTG has potent progestogenic activity similarly to trengestone.[1]

20α-Dihydrotrengestone
Clinical data
Other names20α-DHTG; 20α-Hydroxytrengestone; 6-Chloro-20(S)-hydroxy-9β,10α-pregna-1,4,6-trien-3-one
Drug classProgestin; Progestogen
Pharmacokinetic data
Elimination half-life8–14 hours[1]
Chemical and physical data
FormulaC21H26ClO2
Molar mass345.89 g·mol−1
3D model (JSmol)
SMILES
  • O([H])[C@@](C)[C@]([H])1CC[C@]([H])2[C@@]([H])3C=C(Cl)C4=CC(C=C[C@@]4(C)[C@]3([H])CC[C@@]21C)=O
InChI
  • InChI=1S/C21H26ClO2/c1-12(23)15-4-5-16-14-11-19(22)18-10-13(24)6-8-21(18,3)17(14)7-9-20(15,16)2/h6,8,10-11,14-17,23H,4-5,7,9H2,1-3H3/t14-,15+,16-,17+,20+,21-/m0/s1
  • Key:YOKUOTGYGGEOMR-OAYGGAORSA-N

See also

References
  1. Dixon R, Tormey P, Darragh A (March 1975). "Disposition of the retro-steroid progestogen, 6-chloro-9beta, 10alpha-pregna-1,4,6-triene-3,20-dione (Ro 4-8347), in man". Contraception. 11 (3): 339–46. doi:10.1016/0010-7824(75)90042-6. PMID 1116370.
  2. Breuer H, Kime DE, Knuppen R (September 1973). "Metabolism of 6-chloro-9 beta, 10 alpha-pregna-1,4,6-triene-3,20-dione in rat, rabbit, monkey and man". Acta Endocrinol. 74 (1): 127–43. doi:10.1530/acta.0.0740127. PMID 4202495.


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