Ethinylestradiol sulfamate

Ethinylestradiol sulfamate (developmental code name J1028), or 17α-ethynylestradiol 3-O-sulfamate, is a synthetic estrogen and estrogen ester which was never marketed. It is the C3 sulfamate ester of ethinylestradiol. The drug shows considerably improved oral estrogenic potency (uterotrophic) relative to ethinylestradiol in rats but without an increase in hepatic estrogenic potency. Related compounds like ethinylestradiol N,N-diethylsulfamate (J271) and ethinylestradiol pyrrolidinosulfonate (J272) have also been developed, and have similar properties in animals. However, the closely related compound estradiol sulfamate (E2MATE) failed to show estrogenic activity in humans, which is due to the fact that it is additionally a highly potent inhibitor of steroid sulfatase and prevents its own bioactivation into estradiol.

Not to be confused with Ethinylestradiol sulfate or Ethinylestradiol sulfonate.
Ethinylestradiol sulfamate
Clinical data
Other names17α-Ethynylestradiol 3-O-sulfamate; J1028; EEMATE; EE2MATE; 17α-Ethynylestra-1,3,5(10)-triene-3,17β-diol 3-sulfamate
Routes of
administration		By mouth
Drug classEstrogen; Estrogen ester
Identifiers
  • [(8R,9S,13S,14S,17R)-17-Ethynyl-17-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] sulfamate
CAS Number
PubChem CID
UNII
Chemical and physical data
FormulaC20H25NO4S
Molar mass375.48 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OS(=O)(=O)N
  • InChI=1S/C20H25NO4S/c1-3-20(22)11-9-18-17-6-4-13-12-14(25-26(21,23)24)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,22H,4,6,8-11H2,2H3,(H2,21,23,24)/t16-,17-,18+,19+,20+/m1/s1
  • Key:FIILGZCJKYBWGS-SLHNCBLASA-N
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