Estradiol sulfamate

Estradiol sulfamate
Clinical data
Other names	E2MATE; Estradiol-3-O-sulfamate; (E2-SO2-(NH2); J995; ES-J995; PGL-2; PGL-2001; ZK-190628; BLE-00084; 17β-Hydroxyestra-1,3,5(10)-trien-3-yl sulfamate
Routes of; administration	By mouth
Drug class	Steroid sulfatase inhibitor
Pharmacokinetic data
Elimination half-life	18 days
Identifiers
	IUPAC name [(8R,9S,13S,14S,17S)-17-Hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] sulfamate;
CAS Number	172377-52-5;
PubChem CID	6918339;
DrugBank	DB06597;
ChemSpider	5293543;
UNII	WO55ODW08Z;
ChEMBL	ChEMBL219321;
Chemical and physical data
Formula	C18H25NO4S
Molar mass	351.46 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OS(=O)(=O)N;
	InChI InChI=1S/C18H25NO4S/c1-18-9-8-14-13-5-3-12(23-24(19,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,20H,2,4,6-9H2,1H3,(H2,19,21,22)/t14-,15-,16+,17+,18+/m1/s1; Key:YXYXCSOJKUAPJI-ZBRFXRBCSA-N;

Estradiol sulfamate (E2MATE; developmental code names J995, PGL-2, PGL-2001, ZK-190628, others), or estradiol-3-O-sulfamate, is a steroid sulfatase (STS) inhibitor which is under development for the treatment of endometriosis.^[2]^[3]^[4]^[5] It is the C3 sulfamate ester of estradiol, and was originally thought to be a prodrug of estradiol.^[3]^[4]

^ Cite error: The named reference pmid24604234 was invoked but never defined (see the help page).
^ "PGL 2". AdisInsight. Springer Nature Switzerland AG.
^ ^a ^b Elger W, Barth A, Hedden A, Reddersen G, Ritter P, Schneider B, et al. (2001). "Estrogen sulfamates: a new approach to oral estrogen therapy". Reproduction, Fertility, and Development. 13 (4): 297–305. doi:10.1071/RD01029. PMID 11800168.
^ ^a ^b Thomas MP, Potter BV (September 2015). "Estrogen O-sulfamates and their analogues: Clinical steroid sulfatase inhibitors with broad potential". The Journal of Steroid Biochemistry and Molecular Biology. 153: 160–169. doi:10.1016/j.jsbmb.2015.03.012. PMID 25843211. S2CID 24116740.
^ 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". 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.

[pmid24604234-1] Cite error: The named reference pmid24604234 was invoked but never defined (see the help page).

[AdisInsight-2] "PGL 2". AdisInsight. Springer Nature Switzerland AG.

[pmid11800168-3] Elger W, Barth A, Hedden A, Reddersen G, Ritter P, Schneider B, et al. (2001). "Estrogen sulfamates: a new approach to oral estrogen therapy". Reproduction, Fertility, and Development. 13 (4): 297–305. doi:10.1071/RD01029. PMID 11800168.

[pmid25843211-4] Thomas MP, Potter BV (September 2015). "Estrogen O-sulfamates and their analogues: Clinical steroid sulfatase inhibitors with broad potential". The Journal of Steroid Biochemistry and Molecular Biology. 153: 160–169. doi:10.1016/j.jsbmb.2015.03.012. PMID 25843211. S2CID 24116740.

[pmid8541236-5] 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". 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.

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