Estrone sulfate (medication)

Estrone sulfate (medication)
Clinical data
Other names	E1S; Oestrone sulfate; Estrone 3-sulfate; Estra-1,3,5(10)-trien-17-one 3-sulfate
Routes of; administration	By mouth, others
Drug class	Estrogen; Estrogen ester
Pharmacokinetic data
Protein binding	90%, to albumin, and not to SHBGTooltip sex hormone-binding globulin
Metabolism	Desulfation (via STSTooltip steroid sulfatase)
Metabolites	• Estrone; • Estradiol
Elimination half-life	12 hours
Identifiers
	IUPAC name [(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate;
CAS Number	481-97-0 ; 438-67-5 (sodium); 7280-37-7 (piperazine);
PubChem CID	3001028;
IUPHAR/BPS	4749;
DrugBank	DB04574 ;
ChemSpider	2272513 ;
UNII	QTL48N278K;
ChEBI	CHEBI:17474 ;
ChEMBL	ChEMBL494753 ;
Chemical and physical data
Formula	C18H22O5S
Molar mass	350.43 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=S(=O)(O)Oc1cc4c(cc1)[C@H]3CC[C@@]2(C(=O)CC[C@H]2[C@@H]3CC4)C;
	InChI InChI=1S/C18H22O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,18+/m1/s1 ; Key:JKKFKPJIXZFSSB-CBZIJGRNSA-N ;
	(verify)

Estrone sulfate (E1S) is an estrogen medication and naturally occurring steroid hormone. It is used in menopausal hormone therapy among other indications. As the sodium salt (sodium estrone sulfate), it is the major estrogen component of conjugated estrogens (Premarin) and esterified estrogens (Estratab, Menest). In addition, E1S is used on its own as the piperazine salt estropipate (piperazine estrone sulfate; Ogen). The compound also occurs as a major and important metabolite of estradiol and estrone. E1S is most commonly taken by mouth, but in the form of Premarin can also be taken by parenteral routes such as transdermal, vaginal, and injection.

Clinical data


Other names	E1S; Oestrone sulfate; Estrone 3-sulfate; Estra-1,3,5(10)-trien-17-one 3-sulfate
Routes of administration	By mouth, others
Drug class	Estrogen; Estrogen ester
Pharmacokinetic data
Protein binding	90%, to albumin, and not to SHBGTooltip sex hormone-binding globulin
Metabolism	Desulfation (via STSTooltip steroid sulfatase)
Metabolites	• Estrone • Estradiol
Elimination half-life	12 hours
Identifiers
IUPAC name [(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
CAS Number	481-97-0^Y 438-67-5 (sodium) 7280-37-7 (piperazine)
PubChem CID	3001028
IUPHAR/BPS	4749
DrugBank	DB04574^Y
ChemSpider	2272513^Y
UNII	QTL48N278K
ChEBI	CHEBI:17474^Y
ChEMBL	ChEMBL494753^Y
Chemical and physical data
Formula	C₁₈H₂₂O₅S
Molar mass	350.43 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=S(=O)(O)Oc1cc4c(cc1)[C@H]3CC[C@@]2(C(=O)CC[C@H]2[C@@H]3CC4)C
InChI InChI=1S/C18H22O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,18+/m1/s1^Y Key:JKKFKPJIXZFSSB-CBZIJGRNSA-N^Y
(verify)