Estrone sulfate (medication)

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.

This article is about estrone sulfate as a medication. For its role as a hormone, see Estrone sulfate.
Estrone sulfate (medication)
Clinical data
Other namesE1S; Oestrone sulfate; Estrone 3-sulfate; Estra-1,3,5(10)-trien-17-one 3-sulfate
Routes of
administration		By mouth, others
Drug classEstrogen; Estrogen ester
Pharmacokinetic data
Protein binding90%, to albumin, and not to SHBGTooltip sex hormone-binding globulin
MetabolismDesulfation (via STSTooltip steroid sulfatase)
Metabolites• Estrone
• Estradiol
Elimination half-life12 hours
Identifiers
  • [(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
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC18H22O5S
Molar mass350.43 g·mol−1
3D model (JSmol)
SMILES
  • O=S(=O)(O)Oc1cc4c(cc1)[C@H]3CC[C@@]2(C(=O)CC[C@H]2[C@@H]3CC4)C
  • 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
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