Ethinylestradiol sulfate

Ethinylestradiol sulfate
Clinical data
Other names	EE sulfate; 17Î±-Ethynylestradiol 3-sulfate
Drug class	Estrogen; 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] hydrogen sulfate;
CAS Number	24560-70-1;
PubChem CID	68575;
ChemSpider	61845;
UNII	67P0FM71OZ;
ChEBI	CHEBI:136600;
ChEMBL	ChEMBL1614648;
CompTox Dashboard (EPA)	DTXSID80873219 ;
Chemical and physical data
Formula	C20H24O5S
Molar mass	376.47 gÂ·molâ1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OS(=O)(=O)O;
	InChI InChI=1S/C20H24O5S/c1-3-20(21)11-9-18-17-6-4-13-12-14(25-26(22,23)24)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21H,4,6,8-11H2,2H3,(H,22,23,24)/t16-,17-,18+,19+,20+/m1/s1; Key:WLGIWVFFGMPRLM-SLHNCBLASA-N;

Ethinylestradiol sulfate (EE sulfate), also known as 17Î±-ethynylestradiol 3-sulfate, is an estrogen ester â specifically, the C3 sulfuric acid (sulfate) ester of the synthetic estrogen ethinylestradiol (EE) â and is the major metabolite of EE.^[1]^[2]^[3] Circulating levels of EE sulfate range from 6 to 22 times those of EE when EE is taken orally.^[1]^[2]^[3] EE sulfate can be transformed back into EE (14â21%) via steroid sulfatase, and it has been suggested that EE sulfate may serve as a circulating reservoir for EE, similarly to the case of estrone sulfate with estradiol.^[4]^[5]^[3]^[1] However, the EE sulfate pool with EE is far smaller than the pool of estrone sulfate that occurs with estradiol (with estrone sulfate levels approximately 200-fold higher than estradiol levels on average with oral estradiol).^[1] In addition, in contrast to the case of estrone sulfate and estrone, the conversion rate of EE sulfate back into EE is relatively low, and has been said probably isn't of clinical significance.^[5] However, other studies have suggested that EE sulfate may nonetheless contribute up to 20% of total EE levels.^[2]^[6]