• Source: Stilbestrol

Stilbestrol, or stilboestrol, also known as 4,4'-dihydroxystilbene or 4,4'-stilbenediol, is a stilbenoid nonsteroidal estrogen and the parent compound of a group of more potent nonsteroidal estrogen derivatives that includes, most notably, diethylstilbestrol (DES). The term "stilbestrol" is often used incorrectly to refer to DES, but they are not the same compound.
Stilbestrol itself is an active estrogen but is less potent than DES and other derivatives.




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.




= Mechanism of action

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




= Closely related compounds

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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).




Occupational exposure


Occupational exposure to stilbestrol has resulted in gynaecomastia in workers.




See also


High-dose estrogen




References

Kata Kunci Pencarian:

• Stilbestrol
• List of estrogen esters
• Diethylstilbestrol
• ICI-85966
• Diethylstilbestrol dipalmitate
• Furostilbestrol
• Diethylstilbestrol monobenzyl ether
• Norethisterone
• Fosfestrol
• Diethylstilbestrol dipropionate