Stilbestrol

Stilbestrol
Names
	IUPAC name 4-[(E)-2-(4-Hydroxyphenyl)ethenyl]phenol
	Other names 4,4'-Dihydroxystilbene, 4,4'-stilbenediol
Identifiers
CAS Number	659-22-3;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	4445526;
PubChem CID	5282363;
	InChI InChI=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+ Key: XLAIWHIOIFKLEO-OWOJBTEDSA-N;
	SMILES C1=CC(=CC=C1C=CC2=CC=C(C=C2)O)O; c1cc(ccc1/C=C/c2ccc(cc2)O)O;
Properties
Chemical formula	C14H12O2
Molar mass	212.24388 g/mol
Magnetic susceptibility (χ)	-130·10−6 cm3/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Stilbestrol, or stilboestrol, also known as 4,4'-dihydroxystilbene or 4,4'-stilbenediol, is a stilbenoid and the parent compound of a group of nonsteroidal estrogens that includes, most notably, diethylstilbestrol.[1][2] The term "stilbestrol" is often used incorrectly to refer to diethylstilbestrol, but they are not the same compound.[1]

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.[3]

Mechanism of action

The stilbestrol estrogens bind with high affinity to both ERα and ERβ.[4]

Closely related compounds

Triphenylethylene.

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 silbestrol derivative (it is 3,4',5-stilbenetriol).[5]

Occupational exposure

Occupational exposure to stilboestrol has resulted in gynaecomastia in workers.[6]

References

VITAMINS AND HORMONES. Academic Press. 1 January 1945. pp. 233–. ISBN 978-0-08-086600-0.
William John Edward Jessop (12 May 2014). Fearon's Introduction to Biochemistry. Elsevier. pp. 408–. ISBN 978-1-4831-9556-8.
Actions and Uses of Drugs. Stanford University Press. pp. 234–. ISBN 978-0-8047-1505-8.
Kuiper, George G. J. M.; Carlsson, Bo; Grandien, Kaj; Enmark, Eva; Häggblad, Johan; Nilsson, Stefan; Gustafsson, Jan-Åke (1997). "Comparison of the Ligand Binding Specificity and Transcript Tissue Distribution of Estrogen Receptors α and β". Endocrinology. 138 (3): 863–870. doi:10.1210/endo.138.3.4979. ISSN 0013-7227. PMID 9048584.
Bhat KP, Lantvit D, Christov K, Mehta RG, Moon RC, Pezzuto JM; Lantvit; Christov; Mehta; Moon; Pezzuto (October 2001). "Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models". Cancer Res. 61 (20): 7456–63. PMID 11606380.CS1 maint: multiple names: authors list (link)
Fitzsimons, P.M. (October 1944). "Gynaecomastia in Stilboestrol Workers". Br J Ind Med. 1 (4): 235–237. PMC 1035620.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[AcademicPress1945-1] VITAMINS AND HORMONES. Academic Press. 1 January 1945. pp. 233–. ISBN 978-0-08-086600-0.

[Jessop2014-2] William John Edward Jessop (12 May 2014). Fearon's Introduction to Biochemistry. Elsevier. pp. 408–. ISBN 978-1-4831-9556-8.

[Stanford-3] Actions and Uses of Drugs. Stanford University Press. pp. 234–. ISBN 978-0-8047-1505-8.

[KuiperCarlsson1997-4] Kuiper, George G. J. M.; Carlsson, Bo; Grandien, Kaj; Enmark, Eva; Häggblad, Johan; Nilsson, Stefan; Gustafsson, Jan-Åke (1997). "Comparison of the Ligand Binding Specificity and Transcript Tissue Distribution of Estrogen Receptors α and β". Endocrinology. 138 (3): 863–870. doi:10.1210/endo.138.3.4979. ISSN 0013-7227. PMID 9048584.

[pmid11606380-5] Bhat KP, Lantvit D, Christov K, Mehta RG, Moon RC, Pezzuto JM; Lantvit; Christov; Mehta; Moon; Pezzuto (October 2001). "Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models". Cancer Res. 61 (20): 7456–63. PMID 11606380.CS1 maint: multiple names: authors list (link)

[6] Fitzsimons, P.M. (October 1944). "Gynaecomastia in Stilboestrol Workers". Br J Ind Med. 1 (4): 235–237. PMC 1035620.