Stilbestrol

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Stilbestrol

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Template:Longitem	C14H12O2
Molar mass	212.24388 g/mol
Template:Longitem	−130·10−6 cm3/mol

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

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

Closely related compounds

File:Triphenylethylene.svg

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 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