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Abandoned drugs
Estriol sulfamate
Другие языки:

    Estriol sulfamate

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    Estriol sulfamate
    Estriol 3-sulfamate.svg
    Clinical data
    Other names Estriol 3-O-sulfamate; J1034; E3MATE; Estra-1,3,5(10)-triene-3,16α,17β-triol 3-sulfamate; 16α,17β-Dihydroxyestra-1,3,5(10)-trien-3-yl sulfamate
    Routes of
    administration    		 By mouth
    Drug class Estrogen; Estrogen ester
    Identifiers
    • [(8R,9S,13S,14S,16R,17R)-16,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] sulfamate
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    Chemical and physical data
    Formula C18H25NO5S
    Molar mass 367.46 g·mol−1
    3D model (JSmol)
    • C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)OS(=O)(=O)N
    • InChI=1S/C18H25NO5S/c1-18-7-6-13-12-5-3-11(24-25(19,22)23)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,20-21H,2,4,6-7,9H2,1H3,(H2,19,22,23)/t13-,14-,15+,16-,17+,18+/m1/s1
    • Key:VGHIBOFCBWMZNZ-ZXXIGWHRSA-N

    Estriol sulfamate (developmental code name J1034), or estriol 3-O-sulfamate, is a synthetic estrogen and estrogen ester which was never marketed. It is the C3 sulfamate ester of estriol. The drug shows substantially improved oral estrogenic potency (vagina, uterus) relative to estriol in rats but without an increase in hepatic estrogenic potency. 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 which regulates the estrogenicity of such compounds and thus it prevents its own bioactivation into estradiol.

    See also



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