Ethinylestradiol sulfamate

Not to be confused with Ethinylestradiol sulfate or Ethinylestradiol sulfonate.

Ethinylestradiol sulfamate (developmental code name J1028), or 17α-ethynylestradiol 3-O-sulfamate, is a synthetic estrogen and estrogen ester which was never marketed.^[1][2][3] It is the C3 sulfamate ester of ethinylestradiol.^[1] The drug shows considerably improved oral estrogenic potency (uterotrophic) relative to ethinylestradiol in rats but without an increase in hepatic estrogenic potency.^[1][3] Related compounds like ethinylestradiol N,N-diethylsulfamate (J271) and ethinylestradiol pyrrolidinosulfonate (J272) have also been developed, and have similar properties in animals.^[4] However, the closely related compound estradiol sulfamate (E2MATE) failed to show estrogenic activity in humans, which is because it is additionally a highly potent inhibitor of steroid sulfatase and prevents its own bioactivation into estradiol.^[5]

Ethinylestradiol sulfamate

Clinical data
Other names	17α-Ethynylestradiol 3-O-sulfamate; J1028; EEMATE; EE2MATE; 17α-Ethynylestra-1,3,5(10)-triene-3,17β-diol 3-sulfamate
Routes of administration	By mouth[1]
Drug class	Estrogen; Estrogen ester
Identifiers
IUPAC name [(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	91490-65-2 Y
PubChem CID	9799774
UNII	8MM253B4X2
Chemical and physical data
Formula	C20H25NO4S
Molar mass	375.48 g·mol−1
3D model (JSmol)	Interactive image
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 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

See also

• List of estrogen esters § Esters of other steroidal estrogens