Estrone sulfate

Estrone sulfate

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	481-97-0 438-67-5 (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
3D model (Jmol)	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
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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. However, it is available as estropipate (piperazine estrone sulfate), a salt of E1S and piperazine.^[1]

See also

• Estradiol sulfate
• Estriol glucuronide
• DHEA sulfate
• Pregnenolone sulfate
• Lipoidal estradiol
• Catechol estrogen

References

1. 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. 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.