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]
^ abcdElger W, Schwarz S, Hedden A, Reddersen G, Schneider B (December 1995). "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. doi:10.1016/0960-0760(95)00214-6. PMID 8541236. S2CID 31312.
^US 6080735, 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", issued 27 June 2000, assigned to Sterix Ltd
^ abStella VJ (12 March 2007). "Prodrug Approaches to Enhancing the Oral Delivery of Poorly Permeable Drugs". In Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J (eds.). Prodrugs: Challenges and Rewards. Springer Science & Business Media. p. 58. ISBN 978-0-387-49782-2.
^Elger W, Palme HJ, Schwarz S (April 1998). "Novel oestrogen sulfamates: a new approach to oral hormone therapy". Expert Opinion on Investigational Drugs. 7 (4): 575–589. doi:10.1517/13543784.7.4.575. PMID 15991994.
^Elger W, Wyrwa R, Ahmed G, Meece F, Nair HB, Santhamma B, et al. (January 2017). "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. doi:10.1016/j.jsbmb.2016.07.008. PMID 27449818. S2CID 26650319.
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Ethinylestradiol sulfonate (EES), sold under the brand names Deposiston and Turisteron among others, is an estrogen medication which has been used in birth...
properties and the mechanism by which they occur. Estradiol sulfamate (E2MATE) is a C3 sulfamate ester of estradiol which was developed in the 1990s and was...
Estriol sulfamate (developmental code name J1034), or estriol 3-O-sulfamate, is a synthetic estrogen and estrogen ester which was never marketed. It is...
differs from non-bioidentical estrogens like conjugated estrogens and ethinylestradiol in various ways, with implications for tolerability and safety. Estradiol...
Estrone sulfamate (EMATE; developmental code name J994), or estrone-3-O-sulfamate, is a steroid sulfatase (STS) inhibitor which has not yet been marketed...
differs from non-bioidentical estrogens like conjugated estrogens and ethinylestradiol in various ways, with implications for tolerability and safety. Estradiol...
estrogens like conjugated estrogens (CEEs), and synthetic estrogens like ethinylestradiol Progestogens – bioidentical progesterone, and progestins (synthetic...
12%. Ethinylestradiol is more potent in its effects on liver protein synthesis than either CEEs or estradiol, with 10 μg/day oral ethinylestradiol having...
relevant. Conversely, combined oral contraceptive pills containing ethinylestradiol have considerable effects on coagulation and fibrinolysis. The differences...
potency of oral ethinylestradiol is approximately 30-fold higher than that of parenteral EBB. In accordance, 50 μg/day oral ethinylestradiol has been reported...
PEP is greatly improved relative to synthetic oral estrogens like ethinylestradiol and diethylstilbestrol. PEP was discovered around 1953 and was introduced...
intravenously. EMP and other estrogens such as polyestradiol phosphate and ethinylestradiol are far less costly than newer therapies such as GnRH modulators, abiraterone...
greater incidence of hyperprolactinemia (high prolactin levels) than ethinylestradiol orally at a dose of 100 μg/day (or about 3 mg/month total) (rates of...
coagulation factors is less than that of 10 μg/day oral ethinylestradiol. Oral ethinylestradiol at 10 μg/day has been found to have about 1.5- to 2.5-fold...
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