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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 |
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Chemical and physical data | |
Formula | C20H25NO4S |
Molar mass | 375.48 g·mol−1 |
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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 due to the fact that it is additionally a highly potent inhibitor of steroid sulfatase and prevents its own bioactivation into estradiol. [5]