Estriol sulfamate explained

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. 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^[4] and thus it prevents its own bioactivation into estradiol.^[5]

See also

• List of estrogen esters § Estriol esters

Notes and References

1. Elger W, Palme HJ, Schwarz S . Novel oestrogen sulfamates: a new approach to oral hormone therapy . Expert Opin Investig Drugs . 7 . 4 . 575–89 . April 1998 . 15991994 . 10.1517/13543784.7.4.575 .
2. Schwarz S, Schumacher M, Ring S, Nanninga A, Weber G, Thieme I, Undeutsch B, Elger W . 17Beta-hydroxy-11alpha-(3'-sulfanylpropyl)oxy-estra-1,3,5(10)- trien-3-yl sulfamate--a novel hapten structure: toward the development of a specific enzyme immunoassay (EIA) for estra-1,3,5(10)-triene-3-yl sulfamates . Steroids . 64 . 7 . 460–71 . July 1999 . 10443902 . 10.1016/s0039-128x(99)00020-3. 11533476 .
3. Schwarz, S., Elger, W., Siemann, H. J., Reddersen, G., & Schneider, B. (2000). U.S. Patent No. 6,080,735. Washington, DC: U.S. Patent and Trademark Office. https://patents.google.com/patent/US6080735A/en
4. Chander. S K, A Purohit, L W L Woo, B V L Potter and M J Reed. 2004. The role of steroid sulphatase in regulating the oestrogenicity of oestrogen sulphamates.. Biochem. Biophys. Res. Commun.. 322. 1. 217–222. 10.1016/j.bbrc.2004.07.108. 15313194.
5. Elger W, Wyrwa R, Ahmed G, Meece F, Nair HB, Santhamma B, Killeen Z, Schneider B, Meister R, Schubert H, Nickisch K . Estradiol prodrugs (EP) for efficient oral estrogen treatment and abolished effects on estrogen modulated liver functions . J. Steroid Biochem. Mol. Biol. . 165 . Pt B . 305–311 . January 2017 . 27449818 . 10.1016/j.jsbmb.2016.07.008 . 26650319 .