Estrone sulfate (medication)

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[1][2][3]
Drug classEstrogen; Estrogen ester
Pharmacokinetic data
Protein binding90%, to albumin, and not to SHBGTooltip sex hormone-binding globulin[4]
MetabolismDesulfation (via STSTooltip steroid sulfatase)[6]
Metabolites• Estrone[1]
• Estradiol[1]
Elimination half-life12 hours[5]
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
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
  • 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)

Estrone sulfate (E1S) is an estrogen medication and naturally occurring steroid hormone.[1] It is used in menopausal hormone therapy among other indications.[1][2] As the sodium salt (sodium estrone sulfate), it is the major estrogen component of conjugated estrogens (Premarin) and esterified estrogens (Estratab, Menest).[1][3] In addition, E1S is used on its own as the piperazine salt estropipate (piperazine estrone sulfate; Ogen).[1][3] The compound also occurs as a major and important metabolite of estradiol and estrone.[1] 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.[1][2]

  1. ^ a b c d e f g h i Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  2. ^ a b c "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Retrieved 19 February 2018.
  3. ^ a b c Brucker MC, King TL (8 September 2015). Pharmacology for Women's Health. Jones & Bartlett Publishers. pp. 361–. ISBN 978-1-284-05748-5.
  4. ^ Buchsbaum HJ (6 December 2012). The Menopause. Springer Science & Business Media. pp. 63–64. ISBN 978-1-4612-5525-3.
  5. ^ Wecker L, Watts S, Faingold C, Dunaway G, Crespo L (1 April 2009). Brody's Human Pharmacology. Elsevier Health Sciences. pp. 456–. ISBN 978-0-323-07575-6.
  6. ^ Cite error: The named reference FalconeHurd2013 was invoked but never defined (see the help page).
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