Ethinylestradiol sulfamate

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
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

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.

See also

• List of estrogen esters § Esters of other steroidal estrogens