Stilbestrol, or stilboestrol, also known as 4,4'-dihydroxystilbene or 4,4'-stilbenediol, is a

stilbenoid Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones. Most stilbenoids are prod ...

nonsteroidal estrogen A nonsteroidal estrogen is an estrogen with a nonsteroidal chemical structure. The most well-known example is the stilbestrol estrogen diethylstilbestrol (DES). Although nonsteroidal estrogens formerly had an important place in medicine, they hav ...

and the

parent compound In chemistry, a parent structure is the structure of an unadorned ion or molecule from which derivatives can be visualized. Parent structures underpin systematic nomenclature and facilitate classification. Fundamental parent structures have one o ...

of a group of more potent nonsteroidal estrogen

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...

s that includes, most notably,

diethylstilbestrol Diethylstilbestrol (DES), also known as stilbestrol or stilboestrol, is a nonsteroidal estrogen medication, which is presently rarely used. In the past, it was widely used for a variety of indications, including pregnancy support for those with a ...

(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 Acefluranol (developmental code name BX-591), also known as 2,3-bis(3,4-diacetoxy-5-fluorophenyl)pentane, is a nonsteroidal antiestrogen of the stilbestrol group that was never marketed. It is a polyfluorinated biphenyl that is related to polybr ...

(an antiestrogen) *

Benzestrol Benzestrol (, ) (brand names Chemestrogen, Ocestrol, Octestrol, Octoestrol, Octofollin) is a synthetic nonsteroidal estrogen of the stilbestrol group which was formerly used medically but has since been discontinued. The stilbestrol estrogens, th ...

(''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 Bifluranol (, ; brand name Prostarex; former developmental code name BX-341) is a synthetic nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol that has been used as an antiandrogen in the United Kingdom in the treatmen ...

Dienestrol Dienestrol (, ) (brand names Ortho Dienestrol, Dienoestrol, Dienoestrol Ortho, Sexadien, Denestrolin, Dienol, Dinovex, Follormon, Oestrodiene, Synestrol, numerous others), also known as dienoestrol (), is a synthetic nonsteroidal estrogen of the ...

** Dienestrol acetate *

Diethylstilbestrol Diethylstilbestrol (DES), also known as stilbestrol or stilboestrol, is a nonsteroidal estrogen medication, which is presently rarely used. In the past, it was widely used for a variety of indications, including pregnancy support for those with a ...

(commonly, but erroneously shortened to simply “stilbestrol”) ** Diethylstilbestrol diacetate ** Diethylstilbestrol dilaurate ** Diethylstilbestrol dipalmitate **

Diethylstilbestrol dipropionate Diethylstilbestrol dipropionate (DESDP) (brand names Agostilben, Biokeral, Clinestrol, Cyclen, Estilbin, Estril, Neobenzoestrol, Orestol, Oroestrol, Ostregenin, Prostilbene, Stilbestriol DP, Stilboestrolum Dipropionicum, Stilboestrol, Synestrin, W ...

Diethylstilbestrol disulfate Diethylstilbestrol disulfate (brand names Hydroestryl, Idroestril; former developmental code name M.G. 137) is a synthetic, nonsteroidal estrogen of the stilbestrol group and an ester of diethylstilbestrol Diethylstilbestrol (DES), also known a ...

** Diethylstilbestrol monobenzyl ether **

Dimestrol Dimestrol (brand names Depot-Cyren, Depot-Oestromon), also known as dianisylhexene, 4,4'-dimethoxy-α,α'-diethylstilbene, diethylstilbestrol dimethyl ether, and dimethoxydiethylstilbestrol, is a synthetic nonsteroidal estrogen of the stilbestr ...

(dianisylhexene, diethylstilbestrol dimethyl ether, dimethoxydiethylstilbene) **

Fosfestrol Fosfestrol, sold under the brand name Honvan and also known as diethylstilbestrol diphosphate (DESDP), is an estrogen medication which is used in the treatment of prostate cancer in men. It is given by slow intravenous infusion once per day to on ...

(diethylstilbestrol diphosphate) ** Furostilbestrol (diethylstilbestrol difuroate) **

ICI-85966 ICI-85966 (former tentative brand name Stilbostat), also known as diethylstilbestrol (DES) bis(di(2-chloroethyl)carbamate), is a synthetic, nonsteroidal estrogen and cytostatic antineoplastic agent of the stilbestrol group and a nitrogen mustard e ...

(diethylstilbestrol bis i(2-chloroethyl)carbamate) **_Mestilbol_(diethylstilbestrol_monomethyl_ether) *_Dimethylstilbestrol.html" ;"title="Mestilbol.html" ;"title="i(2-chloroethyl)carbamate) ** Mestilbol">i(2-chloroethyl)carbamate) ** Mestilbol (diethylstilbestrol monomethyl ether) * Dimethylstilbestrol">Mestilbol.html" ;"title="i(2-chloroethyl)carbamate) ** Mestilbol">i(2-chloroethyl)carbamate) ** Mestilbol (diethylstilbestrol monomethyl ether) * Dimethylstilbestrol * Hexestrol (dihydrodiethylstilbestrol) ** Diaethiphenum (hexestrol bis(2-diethylaminoethyl) ether) (a coronary vasodilator) **

Hexestrol diacetate Hexestrol diacetate ( JAN) (brand names Retalon Lingual, Robal, Sintestrol, Sintofolin) is a synthetic, nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol. It is an ester of hexestrol, and was discovered in 1939. See ...

** Hexestrol dicaprylate **

Hexestrol diphosphate Hexestrol diphosphate (brand names Cytostatin, Cytostesin, Pharmestrin, Retalon Aquosum) is a Organic compound#Synthetic compounds, synthetic, nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol and used as an estrogen and ...

Hexestrol dipropionate Hexestrol dipropionate (brand name Hexanoestrol, Retalon Oleosum), or hexestrol dipropanoate, is a synthetic, nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol. It is an ester of hexestrol, and has been known since at l ...

Phenestrol Phenestrol, or fenestrol, also known as hexestrol bis -[bis(2-chloroethyl)aminohenylacetate, is a synthetic compound">synthetic, nonsteroidal estrogen and cytostatic antineoplastic agent (i.e., chemotherapy drug) and a chlorine, chlorphenyl group, ...

(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 Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Par ...

to both

ERα Estrogen receptor alpha (ERα), also known as NR3A1 (nuclear receptor subfamily 3, group A, member 1), is one of two main types of estrogen receptor, a nuclear receptor (mainly found as a chromatin-binding protein) that is activated by the sex ...

and

ERβ Estrogen receptor beta (ERβ) also known as NR3A2 (nuclear receptor subfamily 3, group A, member 2) is one of two main types of estrogen receptor—a nuclear receptor which is activated by the sex hormone estrogen. In humans ERβ is encoded by ...

Closely related compounds

Estrogens closely related to the stilbestrols include

paroxypropione Paroxypropione, also known as paraoxypropiophenone, is a synthetic nonsteroidal estrogen which has been used medically as an antigonadotropin in Spain and Italy but appears to no longer be marketed. It was first synthesized in 1902. The antigona ...

(a metabolite of diethylstilbestrol) and the

anise Anise (; '), also called aniseed or rarely anix is a flowering plant in the family Apiaceae native to Eurasia. The flavor and aroma of its seeds have similarities with some other spices and herbs, such as star anise, fennel, licorice, and ta ...

and

fennel Fennel (''Foeniculum vulgare'') is a flowering plant species in the carrot family. It is a hardy, perennial herb with yellow flowers and feathery leaves. It is indigenous to the shores of the Mediterranean but has become widely naturalized ...

-derived compounds

anol Anol, also known as ''para''-hydroxypropenylbenzene, is a simple phenol that was derived via demethylation from anethole, an estrogenic constituent of anise and fennel, by Sir Charles Dodds in 1937. It was reported to possess extremely potent ...

dianol Dianol is a synthetic, nonsteroidal estrogen that was never marketed. It is a dimer and impurity of anol, and was, along with hexestrol, involved in erroneous findings of highly potent estrogenic activity with anol. Although a potent estrogen, i ...

anethole Anethole (also known as anise camphor) is an organic compound that is widely used as a flavoring substance. It is a derivative of phenylpropene, a type of aromatic compound that occurs widely in nature, in essential oils. It is in the class of p ...

dianethole Dianethole is a naturally occurring organic compound that is found in anise and fennel. It is a dimeric polymer of anethole. It has estrogenic activity, and along with anethole and photoanethole, may be responsible for the estrogenic effects o ...

, and photoanethole (from which the stilbestrol estrogens were actually originally derived). The

triphenylethylene Triphenylethylene (TPE) is a simple aromatic hydrocarbon that possesses weak estrogenic activity. Its estrogenic effects were discovered in 1937. TPE was derived from structural modification of the more potent estrogen diethylstilbestrol, which is ...

group of estrogenic drugs that includes triphenylethylene itself,

estrobin Estrobin, also known as α,α-di(''p''-ethoxyphenyl)-β-phenylbromoethylene and commonly abbreviated as DBE, is a Organic compound#Synthetic compounds, synthetic, nonsteroidal estrogen of the triphenylethylene group that was never marketed. Chlor ...

chlorotrianisene Chlorotrianisene (CTA), also known as tri-''p''-anisylchloroethylene (TACE) and sold under the brand name Tace among others, is a nonsteroidal estrogen related to diethylstilbestrol (DES) which was previously used in the treatment of menopausal ...

, broparestrol,

ethamoxytriphetol Ethamoxytriphetol (developmental code name MER-25) is a synthetic nonsteroidal antiestrogen that was studied clinically in the late 1950s and early 1960s but was never marketed. MER-25 was first reported in 1958, and was the first antiestrogen ...

clomifene Clomifene, also known as clomiphene, is a medication used to treat infertility in women who do not ovulate, including those with polycystic ovary syndrome. Use results in a greater chance of twins. It is taken by mouth once a day, with a course ...

tamoxifen Tamoxifen, sold under the brand name Nolvadex among others, is a selective estrogen receptor modulator used to prevent breast cancer in women and treat breast cancer in women and men. It is also being studied for other types of cancer. It has b ...

, and more recently developed derivatives is also very closely related structurally to the stilbestrols.

Resveratrol Resveratrol (3,5,4′-trihydroxy-''trans''-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi. Sources ...

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 Gynecomastia (also spelled gynaecomastia) is the abnormal non-cancerous enlargement of one or both breasts in males due to the growth of breast tissue as a result of a hormone imbalance between estrogens and androgens. Updated by Brent Wisse (1 ...

in workers.

References

{{Stilbenes Stilbenoids Synthetic estrogens

Stilbestrol derivatives

Mechanism of action

Closely related compounds

Occupational exposure

See also

References