Estrone sulfate

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search

Estrone sulfate
Skeletal formula of estrone sulfate
Space-filling model of the estrone sulfate molecule
Names
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
Other names
E1S; Oestrone sulfate; Estrone 3-sulfate; Estra-1,3,5(10)-trien-17-one 3-sulfate
Identifiers
  • 481-97-0
  • 438-67-5 (sodium salt)
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17474
ChEMBL
  • ChEMBL494753
ChemSpider
  • 2272513
DrugBank
  • DB04574
ECHA InfoCard 100.006.888
EC Number 207-120-4
KEGG
  • C02538
PubChem CID
  • 3001028
UNII
  • QTL48N278K
Properties
C18H22O5S
Molar mass 350.429 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Estrone sulfate (E1S), or estrone 3-sulfate, is a natural, endogenous steroid and an estrogen ester and conjugate.[1]

In addition to its role as a natural hormone, estrone sulfate is used as a medication, for instance in menopausal hormone therapy; for information on estrone sulfate as a medication, see the estrone sulfate (medication) article.

Biological function

E1S itself is biologically inactive, with less than 1% of the relative binding affinity of estradiol for the ERα and ERβ,[2] but it can be converted by steroid sulfatase (also called estrogen sulfatase) into estrone, which is an estrogen.[3] Simultaneously, estrogen sulfotransferases convert estrone to E1S, resulting in an equilibrium between the two steroids in various tissues.[3] E1S is thought to serve as a long-lasting reservoir for estrone and estradiol in the body.[4][5]

Chemistry

E1S, also known as estrone 3-sulfate or as estra-1,3,5(10)-trien-17-one 3-sulfate, is a naturally occurring estrane steroid and a derivative of estrone.[6] It is an estrogen conjugate or ester, and is specifically the C3 sulfate ester of estrone.[6] Related estrogen conjugates include estradiol sulfate, estriol sulfate, estrone glucuronide, estradiol glucuronide, and estriol glucuronide, while related steroid conjugates include dehydroepiandrosterone sulfate and pregnenolone sulfate.

Biochemistry

Metabolism of estrone sulfate in humans[7][8][9]
The image above contains clickable links
This diagram illustrates the metabolic pathways involved in the metabolism of estrogens (i.e., estradiol, estrone, and estriol) in humans.

References

  1. ^ Lobo RA (5 June 2007). Treatment of the Postmenopausal Woman: Basic and Clinical Aspects. Academic Press. pp. 768–. ISBN 978-0-08-055309-2.
  2. ^ Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA (March 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.
  3. ^ a b Falcone T, Hurd WW (22 May 2013). Clinical Reproductive Medicine and Surgery: A Practical Guide. Springer Science & Business Media. pp. 5–6. ISBN 978-1-4614-6837-0.
  4. ^ Melmed S, Polonsky KS, Larsen PR, Kronenberg HM (11 November 2015). Williams Textbook of Endocrinology (13th ed.). Elsevier Health Sciences. pp. 607–. ISBN 978-0-323-34157-8.
  5. ^ Greenblatt JM, Brogan K (27 April 2016). Integrative Therapies for Depression: Redefining Models for Assessment, Treatment and Prevention. CRC Press. pp. 198–. ISBN 978-1-4987-0230-0.
  6. ^ a b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 900–. ISBN 978-1-4757-2085-3.
  7. ^ Buchsbaum HJ, ed. (2012). The Menopause (Clinical Perspectives in Obstetrics and Gynecology). New York, NY: Springer Science & Business Media. p. 64. ISBN 9781461255253.
  8. ^ Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric : the Journal of the International Menopause Society. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947.
  9. ^ "EC 2.4.1.17 – glucuronosyltransferase and Organism(s) Homo sapiens". BRENDA. Technische Universität Braunschweig. January 2018. Retrieved 10 August 2018.

Further reading

  • Rezvanpour A, Don-Wauchope AC (March 2017). "Clinical implications of estrone sulfate measurement in laboratory medicine". Critical Reviews in Clinical Laboratory Sciences. 54 (2): 73–86. doi:10.1080/10408363.2016.1252310. PMID 27960570.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Estrone_sulfate&oldid=854679027"
This content was retrieved from Wikipedia : http://en.wikipedia.org/wiki/Estrone_sulfate
This page is based on the copyrighted Wikipedia article "Estrone sulfate"; it is used under the Creative Commons Attribution-ShareAlike 3.0 Unported License (CC-BY-SA). You may redistribute it, verbatim or modified, providing that you comply with the terms of the CC-BY-SA