Stilbestrol

{{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 nonsteroidal estrogen<ref name="pmid4276416">{{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 }}</ref> and the parent compound of a group of more potent nonsteroidal estrogen derivatives that includes, most notably, diethylstilbestrol (DES).<ref name="pmid4276416" /><ref name="AcademicPress1945">{{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]–}}</ref><ref name="Jessop2014">{{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–}}</ref> The term "stilbestrol" is often used incorrectly to refer to DES, but they are not the same compound.<ref name="AcademicPress1945" />

Stilbestrol itself is an active estrogen but is less potent than DES and other derivatives.<ref name="pmid4276416" />

==Stilbestrol derivatives== The stilbestrol estrogenic drugs include the following:

* Acefluranol (an antiestrogen) * Benzestrol (''technically'' not a stilbestrol derivative due to its elongated central chain, but a very close analogue and grouped with the stilbestrol estrogens in any case) * Bifluranol * Dienestrol ** Dienestrol acetate * Diethylstilbestrol (commonly, but erroneously shortened to simply “stilbestrol”) ** Diethylstilbestrol diacetate ** Diethylstilbestrol dilaurate ** Diethylstilbestrol dipalmitate ** Diethylstilbestrol dipropionate ** Diethylstilbestrol disulfate ** Diethylstilbestrol monobenzyl ether ** Dimestrol (dianisylhexene, diethylstilbestrol dimethyl ether, dimethoxydiethylstilbene) ** Fosfestrol (diethylstilbestrol diphosphate) ** Furostilbestrol (diethylstilbestrol difuroate) ** ICI-85966 (diethylstilbestrol bis[di(2-chloroethyl)carbamate) ** Mestilbol (diethylstilbestrol monomethyl ether) * Dimethylstilbestrol * Hexestrol (dihydrodiethylstilbestrol) ** Diaethiphenum (hexestrol bis(2-diethylaminoethyl) ether) (a coronary vasodilator) ** Hexestrol diacetate ** Hexestrol dicaprylate ** Hexestrol diphosphate ** Hexestrol dipropionate ** Phenestrol (hexestrol bis[4-[bis(2-chloroethyl)amino]phenylacetate) * Methestrol (promethestrol; dimethylhexestrol) ** Methestrol dipropionate (promethestrol dipropionate) * Pentafluranol * Terfluranol

Of the stilbestrol estrogens, diethylstilbestrol, hexestrol, and benzestrol are the most well-known.<ref name="Stanford">{{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–}}</ref>

===Mechanism of action=== The stilbestrol estrogens bind with high affinity to both ERα and ERβ.<ref name="KuiperCarlsson1997">{{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}}</ref>

Estrogens closely related to the stilbestrols include paroxypropione (a metabolite of diethylstilbestrol) and the anise and fennel-derived compounds anol, dianol, anethole, dianethole, and photoanethole (from which the stilbestrol estrogens were actually originally derived). The triphenylethylene group of estrogenic drugs that includes triphenylethylene itself, estrobin, chlorotrianisene, broparestrol, ethamoxytriphetol, clomifene, tamoxifen, and more recently developed derivatives is also very closely related structurally to the stilbestrols.

Resveratrol is a stilbenoid with estrogenic properties that is not technically a stilbestrol derivative (it is 3,4',5-stilbenetriol).<ref name="pmid11606380">{{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 }}</ref>

==Occupational exposure== Occupational exposure to stilbestrol has resulted in gynaecomastia in workers.<ref>{{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 }}</ref>

==See also== * High-dose estrogen

==References== {{Reflist}}

Category:Stilbenoids Category:Synthetic estrogens