Estrone sulfate

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Estrone sulfate
Skeletal formula of estrone sulfate
Space-filling model of the estrone sulfate molecule
Clinical data
Routes of
administration
Oral[1]
Pharmacokinetic data
Biological half-life 12 hours[2]
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 YesY
438-67-5 (sodium)
7280-37-7 (piperazine)
PubChem (CID) 3001028
IUPHAR/BPS 4749
DrugBank DB04574 YesY
ChemSpider 2272513 YesY
UNII QTL48N278K YesY
ChEBI CHEBI:17474 YesY
ChEMBL CHEMBL494753 YesY
Chemical and physical data
Formula C18H22O5S
Molar mass 350.43 g/mol
3D model (Jmol) Interactive image
  (verify)

Estrone sulfate (E1S), or 17β-estrone 3-sulfate, is a natural, endogenous steroid and an estrogen ester.[3] E1S itself is biologically inactive, with less than 1% of the relative binding affinity of estradiol for the ERα and ERβ,[4] but it can be converted by steroid sulfatase (also called estrogen sulfatase) into estrone, which is an estrogen.[5] Simultaneously, estrogen sulfotransferases convert estrone to E1S, resulting in an equilibrium between the two steroids in various tissues.[5] E1S is thought to serve as a long-lasting reservoir for estrone and estradiol in the body.[6][7] In addition to its biological role, as the sodium salt, sodium estrone sulfate, E1S is the primary active estrogen in conjugated equine estrogens (Premarin) and esterified estrogens.[1] Aside from its presence in these estrogen formulations, E2S is not available as a commercial pharmaceutical drug.[citation needed] However, it is available as estropipate (piperazine estrone sulfate), a salt of E1S and piperazine.[1]

See also[edit]

References[edit]

  1. ^ a b c Mary C. Brucker; Tekoa L. King (8 September 2015). Pharmacology for Women’s Health. Jones & Bartlett Publishers. pp. 361–. ISBN 978-1-284-05748-5. 
  2. ^ Lynn Wecker; Stephanie Watts; Carl Faingold; George Dunaway; Lynn Crespo (1 April 2009). Brody's Human Pharmacology. Elsevier Health Sciences. pp. 456–. ISBN 0-323-07575-4. 
  3. ^ Rogerio A. Lobo (5 June 2007). Treatment of the Postmenopausal Woman: Basic and Clinical Aspects. Academic Press. pp. 768–. ISBN 978-0-08-055309-2. 
  4. ^ Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA (1997). "Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta". Endocrinology. 138 (3): 863–70. doi:10.1210/endo.138.3.4979. PMID 9048584. 
  5. ^ a b Tommaso Falcone; William W. Hurd (22 May 2013). Clinical Reproductive Medicine and Surgery: A Practical Guide. Springer Science & Business Media. pp. 5–6. ISBN 978-1-4614-6837-0. 
  6. ^ Shlomo Melmed; Kenneth S. Polonsky; P. Reed Larsen; Henry M. Kronenberg (11 November 2015). Williams Textbook of Endocrinology (13th ed.). Elsevier Health Sciences. pp. 607–. ISBN 978-0-323-34157-8. 
  7. ^ James M. Greenblatt; Kelly Brogan (27 April 2016). Integrative Therapies for Depression: Redefining Models for Assessment, Treatment and Prevention. CRC Press. pp. 198–. ISBN 978-1-4987-0230-0.