# Stilbestrol
> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Stilbestrol
> Markdown URL: https://mediated.wiki/source/Stilbestrol.md
> Source: https://en.wikipedia.org/wiki/Stilbestrol
> Source revision: 1329013432
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{{Distinguish|Diethylstilbestrol}}
{{Chembox
| ImageFile = Stilbestrol.svg
| ImageClass = skin-invert-image
| ImageSize = 250
| ImageAlt =
| PIN = 4,4′-[(''E'')-Ethene-1,2-diyl]diphenol
| OtherNames = Dihydroxystilbene; 4,4'-Dihydroxystilbene, 4,4'-stilbenediol
| Section1 = {{Chembox Identifiers
| CASNo = 659-22-3
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6DRS5V9W5C
| PubChem = 5282363
| SMILES = C1=CC(=CC=C1C=CC2=CC=C(C=C2)O)O
| ChemSpiderID = 4445526
| SMILES2 = c1cc(ccc1/C=C/c2ccc(cc2)O)O
| StdInChI = 1S/C14H12O2/c15-13-7-3-11(4-8-13)1-2-12-5-9-14(16)10-6-12/h1-10,15-16H/b2-1+
| StdInChIKey = XLAIWHIOIFKLEO-OWOJBTEDSA-N
}}
| Section2 = {{Chembox Properties
| Formula = C14H12O2
| MolarMass = 212.24388 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
| MagSus = −130·10−6 cm3/mol
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
'''Stilbestrol''', or '''stilboestrol''', also known as '''4,4'-dihydroxystilbene''' or '''4,4'-stilbenediol''', is a [stilbenoid](/source/stilbenoid) [nonsteroidal estrogen](/source/nonsteroidal_estrogen)[{{cite journal | vauthors = Noller KL, Fish CR | title = Diethylstilbestrol usage: Its interesting past, important present, and questionable future | journal = Med. Clin. North Am. | volume = 58 | issue = 4 | pages = 793–810 | date = July 1974 | pmid = 4276416 | doi = 10.1016/s0025-7125(16)32122-8 }}] and the [parent compound](/source/parent_compound) of a group of more [potent](/source/potency_(pharmacology)) nonsteroidal estrogen [derivative](/source/chemical_derivative)s that includes, most notably, [diethylstilbestrol](/source/diethylstilbestrol) (DES).[{{cite book|title=VITAMINS AND HORMONES|url=https://archive.org/details/in.ernet.dli.2015.5563|date=1 January 1945|publisher=Academic Press|isbn=978-0-08-086600-0|pages=[https://archive.org/details/in.ernet.dli.2015.5563/page/n253 233]–}}][{{cite book|author=William John Edward Jessop|title=Fearon's Introduction to Biochemistry|url=https://books.google.com/books?id=bEGQBQAAQBAJ&pg=PA408|date=12 May 2014|publisher=Elsevier|isbn=978-1-4831-9556-8|pages=408–}}] The term "stilbestrol" is often used incorrectly to refer to DES, but they are not the same compound.[{{cite book|title=Actions and Uses of Drugs|url=https://books.google.com/books?id=02qmAAAAIAAJ&pg=PA234|publisher=Stanford University Press|isbn=978-0-8047-1505-8|pages=234–}}]
===Mechanism of action===
The stilbestrol estrogens bind with high [affinity](/source/affinity_(pharmacology)) to both [ERα](/source/ER%CE%B1) and [ERβ](/source/ER%CE%B2).[{{cite journal|last1=Kuiper|first1=George G. J. M.|last2=Carlsson|first2=Bo|last3=Grandien|first3=Kaj|last4=Enmark|first4=Eva|last5=Häggblad|first5=Johan|last6=Nilsson|first6=Stefan|last7=Gustafsson|first7=Jan-Åke|title=Comparison of the Ligand Binding Specificity and Transcript Tissue Distribution of Estrogen Receptors α and β|journal=Endocrinology|volume=138|issue=3|year=1997|pages=863–870|issn=0013-7227|doi=10.1210/endo.138.3.4979|pmid=9048584|doi-access=free}}]
{{Affinities of estrogen receptor ligands for the ERα and ERβ}}
===Closely related compounds===
[[File:Triphenylethylene.svg|thumb|right|150px|class=skin-invert-image|[Triphenylethylene](/source/Triphenylethylene).]]
Estrogens closely related to the stilbestrols include [paroxypropione](/source/paroxypropione) (a metabolite of diethylstilbestrol) and the [anise](/source/anise) and [fennel](/source/fennel)-derived compounds [anol](/source/anol), [dianol](/source/dianol), [anethole](/source/anethole), [dianethole](/source/dianethole), and [photoanethole](/source/photoanethole) (from which the stilbestrol estrogens were actually originally derived). The [triphenylethylene](/source/triphenylethylene) group of estrogenic drugs that includes triphenylethylene itself, [estrobin](/source/estrobin), [chlorotrianisene](/source/chlorotrianisene), [broparestrol](/source/broparestrol), [ethamoxytriphetol](/source/ethamoxytriphetol), [clomifene](/source/clomifene), [tamoxifen](/source/tamoxifen), and more recently developed derivatives is also very closely related structurally to the stilbestrols.
[Resveratrol](/source/Resveratrol) is a stilbenoid with estrogenic properties that is not technically a stilbestrol derivative (it is 3,4',5-stilbenetriol).[{{cite journal | author = Bhat KP, Lantvit D, Christov K, Mehta RG, Moon RC, Pezzuto JM | title = Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models | journal = Cancer Res. | volume = 61 | issue = 20 | pages = 7456–63 | date = October 2001 | pmid = 11606380 | last2 = Lantvit | last3 = Christov | last4 = Mehta | last5 = Moon | last6 = Pezzuto }}]
==Occupational exposure==
Occupational exposure to stilbestrol has resulted in [gynaecomastia](/source/gynaecomastia) in workers.[{{cite journal |last1=Fitzsimons |first1=P.M. |title=Gynaecomastia in Stilboestrol Workers |journal=Br J Ind Med |date=October 1944 |volume=1 |issue=4 |pages=235–237 |pmc=1035620 }}]
==See also==
* [High-dose estrogen](/source/High-dose_estrogen)
==References==
{{Reflist}}
{{Estrogens and antiestrogens}}
{{Estrogen receptor modulators}}
{{Stilbenes}}
Category:Stilbenoids
Category:Synthetic estrogens
---
Adapted from the Wikipedia article [Stilbestrol](https://en.wikipedia.org/wiki/Stilbestrol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Stilbestrol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.