Estriol sulfamate

Estriol sulfamate
Clinical data
Other names	Estriol 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
Drug class	Estrogen; Estrogen ester
Identifiers
	IUPAC name [(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	175219-34-8 ;
PubChem CID	9864027;
ChemSpider	8039721;
UNII	8VUN4GN4UP;
Chemical and physical data
Formula	C18H25NO5S
Molar mass	367.46 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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;

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]

References

^ ^a ^b ^c ^d 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.
^ ^a ^b ^c Schwarz S, Schumacher M, Ring S, Nanninga A, Weber G, Thieme I, Undeutsch B, Elger W (July 1999). "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. doi:10.1016/s0039-128x(99)00020-3. PMID 10443902. S2CID 11533476.
^ 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
^ 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. doi:10.1016/j.bbrc.2004.07.108. PMID 15313194.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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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[pmid15991994-1] 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.

[pmid10443902-2] Schwarz S, Schumacher M, Ring S, Nanninga A, Weber G, Thieme I, Undeutsch B, Elger W (July 1999). "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. doi:10.1016/s0039-128x(99)00020-3. PMID 10443902. S2CID 11533476.

[SchwarzElger2000-3] 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. doi:10.1016/j.bbrc.2004.07.108. PMID 15313194.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[pmid27449818-5] 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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Clinical data

Other names	Estriol 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 class	Estrogen; Estrogen ester
Identifiers
IUPAC name [(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	175219-34-8^Y
PubChem CID	9864027
ChemSpider	8039721
UNII	8VUN4GN4UP
Chemical and physical data
Formula	C₁₈H₂₅NO₅S
Molar mass	367.46 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES 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 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

Estriol sulfamate

See also

References