Estrone sulfate

Estrone sulfate
Clinical data
Routes of; administration	Oral
Pharmacokinetic data
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 ;
CompTox Dashboard (EPA)	DTXSID50891501 ;
ECHA InfoCard	100.006.888
Chemical and physical data
Formula	C18H22O5S
Molar mass	350.43 g/mol 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), 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]

References

^ ^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.
^ 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.
^ 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.
^ 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.
^ ^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.
^ 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.
^ 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.

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