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Estriol sulfamate

Chemical compound From Wikipedia, the free encyclopedia

Estriol sulfamate (developmental code name J1034), or estriol 3-O-sulfamate, is a synthetic estrogen and estrogen ester which was never marketed.[1][2][3] It is the C3 sulfamate ester of estriol.[1][2] The drug shows substantially improved oral estrogenic potency (vagina, uterus) relative to estriol in rats but without an increase in hepatic estrogenic potency.[1] 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[4] and thus it prevents its own bioactivation into estradiol.[5]

Other namesEstriol 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
administrationBy mouth[1][2]
Drug classEstrogen; Estrogen ester
CAS Number
Quick facts Clinical data, Other names ...
Estriol sulfamate
Clinical data
Other namesEstriol 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[1][2]
Drug classEstrogen; 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
FormulaC18H25NO5S
Molar mass367.46 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
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