Ethinylestradiol sulfamate

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]

Not to be confused with Ethinylestradiol sulfate or Ethinylestradiol sulfonate.
Ethinylestradiol sulfamate
Clinical data
Other names17α-Ethynylestradiol 3-O-sulfamate; J1028; EEMATE; EE2MATE; 17α-Ethynylestra-1,3,5(10)-triene-3,17β-diol 3-sulfamate
Routes of
administration		By mouth[1]
Drug classEstrogen; Estrogen ester
Identifiers
IUPAC name
  • [(8R,9S,13S,14S,17R)-17-Ethynyl-17-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] sulfamate
CAS Number
PubChem CID
UNII
Chemical and physical data
FormulaC20H25NO4S
Molar mass375.48 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OS(=O)(=O)N
InChI
  • InChI=1S/C20H25NO4S/c1-3-20(22)11-9-18-17-6-4-13-12-14(25-26(21,23)24)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,22H,4,6,8-11H2,2H3,(H2,21,23,24)/t16-,17-,18+,19+,20+/m1/s1
  • Key:FIILGZCJKYBWGS-SLHNCBLASA-N

See also

References
  1. Elger 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". J. Steroid Biochem. Mol. Biol. 55 (3–4): 395–403. doi:10.1016/0960-0760(95)00214-6. PMID 8541236. S2CID 31312.
  2. 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
  3. Valentino Stella; Ronald Borchardt; Michael Hageman; Reza Oliyai, Hans Maag, Jefferson Tilley (12 March 2007). Prodrugs: Challenges and Rewards. Springer Science & Business Media. p. 58. ISBN 978-0-387-49782-2.{{cite book}}: CS1 maint: multiple names: authors list (link)
  4. Elger W, Palme HJ, Schwarz S (April 1998). "Novel oestrogen sulfamates: a new approach to oral hormone therapy". Expert Opin Investig Drugs. 7 (4): 575–89. doi:10.1517/13543784.7.4.575. PMID 15991994.
  5. Elger W, Wyrwa R, Ahmed G, Meece F, Nair HB, Santhamma B, Killeen Z, Schneider B, Meister R, Schubert H, Nickisch K (January 2017). "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. doi:10.1016/j.jsbmb.2016.07.008. PMID 27449818. S2CID 26650319.


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