Ethinylestradiol sulfamate explained

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. 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.^[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]

See also

• List of estrogen esters § Esters of other steroidal estrogens

Notes and References

1. Elger W, Schwarz S, Hedden A, Reddersen G, Schneider B . Sulfamates of various estrogens are prodrugs with increased systemic and reduced hepatic estrogenicity at oral application . The Journal of Steroid Biochemistry and Molecular Biology . 55 . 3–4 . 395–403 . December 1995 . 8541236 . 10.1016/0960-0760(95)00214-6 . 31312 .
2. Schwarz S, Elger W, Siemann HJ, Reddersen G, Schneider B . Estra-1,3,5(10)-trien derivatives, processes for their preparation and pharmaceutical compositions containing these compounds . Sterix Ltd . 27 June 2000 . US . 6080735 .
3. Book: Stella VJ . Prodrug Approaches to Enhancing the Oral Delivery of Poorly Permeable Drugs . Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J . Prodrugs: Challenges and Rewards. https://books.google.com/books?id=qkjHxX5TgHEC&pg=RA1-PA32. 12 March 2007. Springer Science & Business Media. 978-0-387-49782-2. 58.
4. Elger W, Palme HJ, Schwarz S . Novel oestrogen sulfamates: a new approach to oral hormone therapy . Expert Opinion on Investigational Drugs . 7 . 4 . 575–589 . April 1998 . 15991994 . 10.1517/13543784.7.4.575 .
5. Elger W, Wyrwa R, Ahmed G, Meece F, Nair HB, Santhamma B, Killeen Z, Schneider B, Meister R, Schubert H, Nickisch K . 6 . Estradiol prodrugs (EP) for efficient oral estrogen treatment and abolished effects on estrogen modulated liver functions . The Journal of Steroid Biochemistry and Molecular Biology . 165 . Pt B . 305–311 . January 2017 . 27449818 . 10.1016/j.jsbmb.2016.07.008 . 26650319 .