Epostane

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Epostane
200px
Names
Other names
Win-32729
Identifiers
Jmol 3D model Interactive image
PubChem 6917713
  • InChI=1S/C22H31NO3/c1-18-8-6-16-14(15(18)7-9-20(18,3)25)5-10-22-19(16,2)11-13(12-23)17(24)21(22,4)26-22/h14-16,24-25H,5-11H2,1-4H3/t14-,15-,16-,18-,19+,20-,21+,22-/m0/s1
    Key: CETKWEWBSMKADK-GSXVSZIWSA-N
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@]45[C@@]3(CC(=C([C@]4(O5)C)O)C#N)C
Properties
C22H31NO3
Molar mass 357.49 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Epostane (INN, USAN, BAN) (developmental code name WIN-32729) is an inhibitor of 3β-hydroxysteroid dehydrogenase (3β-HSD) that was developed as an contraceptive, abortifacient, and oxytocic drug but was never marketed.[1][2] By inhibiting 3β-HSD, epostane blocks the biosynthesis of progesterone from pregnenolone (and also the conversion of dehydroepiandrosterone to androstenedione), thereby functioning as an antiprogestogen and terminating pregnancy.[1] The drug was trialed and in a study was found to be slightly more effective at inducing abortion relative to mifepristone.[3]

Synthesis

File:Epostane synthesis.png
Epostane synthesis: Sterling Drug, R. G. Christiansen, DE 2855091  (1979).

References

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  1. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
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