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Stilboestrol
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 ** Diethy ...
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Diethylstilbestrol Dipropionate
Diethylstilbestrol dipropionate (DESDP) (brand names Agostilben, Biokeral, Clinestrol, Cyclen, Estilbin, Estril, Neobenzoestrol, Orestol, Oroestrol, Ostregenin, Prostilbene, Stilbestriol DP, Stilboestrolum Dipropionicum, Stilboestrol, Synestrin, Willestrol, others), or diethylstilbestrol dipropanoate, also known as stilboestrol dipropionate (), is a synthetic nonsteroidal estrogen of the stilbestrol group that was formerly marketed widely throughout Europe. It is an ester of diethylstilbestrol with propionic acid, and is more slowly absorbed in the body than diethylstilbestrol. The medication has been said to be one of the most potent estrogens known. The medication has been available in both oral and intramuscular formulations. See also * List of estrogen esters § Diethylstilbestrol esters * List of sex-hormonal aqueous suspensions This is a list of known sex-hormonal crystalline aqueous suspension formulations. Brand names and developmental code names are in parenth ...
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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 history of recurrent miscarriage, hormone therapy for menopausal symptoms and estrogen deficiency, treatment of prostate cancer and breast cancer, and other uses. By 2007, it was only used in the treatment of prostate cancer and breast cancer. In 2011, Hoover and colleagues reported on adverse health outcomes linked to DES including infertility, miscarriage, ectopic pregnancy, preeclampsia, preterm birth, stillbirth, infant death, menopause prior to age 45, breast cancer, cervical cancer, and vaginal cancer. While most commonly taken by mouth, DES was available for use by other routes as well, for instance, vaginal, topical, and by injection. DES is an estrogen, or an agonist of the estrogen receptors, the biological target of es ...
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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 produced by plants, and the only known exception is the antihelminthic and antimicrobial stilbenoid, 2-isopropyl-5- ''E'')-2-phenylvinylenzene-1,3-diol, biosynthesized by the Gram-negative bacterium ''Photorhabdus luminescens.'' Chemistry Stilbenoids are hydroxylated derivatives of stilbene and have a C6–C2–C6 structure. They belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones. Under UV irradiation, stilbene and its derivatives undergo intramolecular cyclization, called stilbene photocyclization to form dihydrophenanthrenes. Oligomeric forms are known as oligostilbenoids. Types ;Aglycones * Piceatannol in the roots of Norway spruces * Pinosylvin is a fungal toxin protecting wood ...
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Dimethylstilbestrol
Dimethylstilbestrol (DMS) is a nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol which was never marketed. It is a so-called "weak", "impeded", or "short-acting" estrogen similarly to estriol and ''meso''-butoestrol. The affinity of DMS for the ER was reported as about 10% of that of estradiol. For comparison, diethylstilbestrol had 140% of the affinity of estradiol for the ER. The endometrial proliferation dose of DMS in women is 20 mg. A single 12 mg intramuscular injection Intramuscular injection, often abbreviated IM, is the injection of a substance into a muscle. In medicine, it is one of several methods for parenteral administration of medications. Intramuscular injection may be preferred because muscles have ... of DMS has a duration of approximately 12 days in humans. References Abandoned drugs Phenols Stilbenoids Synthetic estrogens {{Genito-urinary-drug-stub ...
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Furostilbestrol
Furostilbestrol (INN), also known as diethylstilbestrol di(2-furoate) or simply as diesthylstilbestrol difuroate, is a synthetic, nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol that was never marketed. It is an ester of diethylstilbestrol and was described in the literature in 1952. See also * Diethylstilbestrol dipropionate * Dimestrol * 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 ... * Mestilbol References Estrogen esters Phenols Stilbenoids Synthetic estrogens Abandoned drugs {{genito-urinary-drug-stub ...
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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 ester of diethylstilbestrol (DES) which was developed for the treatment of breast cancer and prostate cancer Prostate cancer is cancer of the prostate. Prostate cancer is the second most common cancerous tumor worldwide and is the fifth leading cause of cancer-related mortality among men. The prostate is a gland in the male reproductive system that su ... but was never marketed (possibly due to the toxicity of DES). See also * List of hormonal cytostatic antineoplastic agents * List of estrogen esters References Abandoned drugs Antineoplastic drugs Estrogen esters Hormonal antineoplastic drugs Carbamates Phenols Synthetic estrogens Chloroethyl compounds {{Genito-urinary-drug-stub ...
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Mestilbol
Mestilbol (brand name Monomestro or Monomestrol), also known as diethylstilbestrol monomethyl ether, is a synthetic nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol. It was developed by Wallace & Tiernan Company, patented in 1940, and introduced for medical use in the 1940s, but is now no longer marketed. Mestilbol was available both as oral tablets and in oil for intramuscular injection. The drug is gradually demethylated in the body into diethylstilbestrol and hence is a prodrug of diethylstilbestrol. Mestilbol is a highly active estrogen Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal a ..., although somewhat less so than diethylstilbestrol, but is longer-lasting in comparison. See also * List of estrogen esters § Ethers of nonsteroidal estrogens ...
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Hexestrol
Hexestrol, sold under the brand name Synestrol among others, is a nonsteroidal estrogen which was previously used for estrogen replacement therapy and in the treatment of certain hormone-dependent cancers as well as gynecological disorders but is mostly no longer marketed. It has also been used in the form of esters such as hexestrol diacetate (brand name Sintestrol) and hexestrol dipropionate (brand name Hexanoestrol). Hexestrol and its esters are taken by mouth, held under the tongue, or via injection into muscle. Medical uses Hexestrol has been used in estrogen replacement therapy, for the treatment of breast cancer in women and prostate cancer in men, and for the treatment of certain gynecological disorders. Pharmacology Pharmacodynamics Hexestrol has approximately 302% and 234% of the affinity of estradiol for the estrogen receptors (ERs) ERα and ERβ, respectively. The affinity of hexestrol for the ERs is said to be similar to or slightly higher than that of es ...
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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 stilbestrol group which is related to diethylstilbestrol. It has been used clinically as a hormonal therapy in cases of delayed female puberty, hypogonadism, menopausal, and postmenopausal symptoms. It is known to induce the development of female secondary sexual characteristics in the case of female delayed puberty or hypogonadism. The drug has also been used as a growth promoter in livestock. DES is a known endocrine disrupting chemical. Molecularly, it is known to increase the risk of aneuploidy via interference with microtubule assembly. Prior to the 1950s, DES was widely prescribed to pregnant women to prevent miscarriage and preterm labor. A study released in the 1950s found that women who were exposed to DES were at increased risk for ...
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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 also * Hexestrol dicaprylate * Hexestrol diphosphate * 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 ... References Acetate esters Estrogen esters Phenols Stilbenoids Synthetic estrogens {{genito-urinary-drug-stub ...
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