Triphenylbromoethylene

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Triphenylbromoethylene
Triphenylbromoethylene.png
Clinical data
Trade names Bromylene, Eitriphin, Oestronyl, Prostilban, Tribenorm
Other namesTPBE; Tribromophenylethylene; Bromotriphenylethylene; Phenylstilbene bromide; Fenbrostilbenum
Drug class Nonsteroidal estrogen
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C20H15Br
Molar mass 335.244 g·mol−1
3D model (JSmol)

Triphenylbromoethylene (TPBE; brand names Bromylene, Eitriphin, Oestronyl, Prostilban, Tribenorm), also known as bromotriphenylethylene or as phenylstilbene bromide, is a synthetic nonsteroidal estrogen of the triphenylethylene group that was marketed in the 1940s similarly to the closely related estrogen triphenylchloroethylene. [1] [2]

A diethoxylated derivative of triphenylbromoethylene, estrobin (DBE), is also an estrogen, but, in contrast, was never marketed. [3] An ethylated derivative of triphenylbromoethylene, broparestrol (BDPE), is a selective estrogen receptor modulator (SERM) that has been marketed. [4] [5]

See also

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Metenolone enanthate chemical compound

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Lynestrenol chemical compound

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Mestranol chemical compound

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Mibolerone chemical compound

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Drostanolone propionate chemical compound

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Mestanolone chemical compound

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Drostanolone chemical compound

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Noretynodrel chemical compound

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Benzestrol chemical compound

Benzestrol is a synthetic nonsteroidal estrogen of the stilbestrol group which was formerly used medically but has since been discontinued. The stilbestrol estrogens, the most well-known of which is diethylstilbestrol (DES) were used extensively in the mid-1900s and were finally banned by the FDA due to them causing tumors in the children of women who used them.

Quinestradol chemical compound

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Cloxestradiol chemical compound

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Nilestriol

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Doisynolic acid group of stereoisomers

Doisynolic acid is a synthetic, nonsteroidal, orally active estrogen that was never marketed. The reaction of estradiol or estrone with potassium hydroxide, a strong base, results in doisynolic acid as a degradation product, which retains high estrogenic activity, and this reaction was how the drug was discovered, in the late 1930s. The drug is a highly active and potent estrogen by the oral or subcutaneous route. The reaction of equilenin or dihydroequilenin with potassium hydroxide was also found to produce bisdehydrodoisynolic acid, the levorotatory isomer of which is an estrogen with an "astonishingly" high degree of potency, while the dextrorotatory isomer is inactive. Doisynolic acid was named after Edward Adelbert Doisy, a pioneer in the field of estrogen research and one of the discoverers of estrone.

Hydroxyestrone diacetate

Hydroxyestrone diacetate, or 16α-hydroxyestrone diacetate, also known as 3,16α-dihydroxyestra-1,3,5(10)-trien-17-one 3,16α-diacetate, is a synthetic, steroidal estrogen which has been marketed in France, Spain, Brazil, and Argentina. It is a derivative of 16α-hydroxyestrone with an acetate esters attached at the C3 and C16α positions.

Bisdehydrodoisynolic acid chemical compound

Bisdehydrodoisynolic acid (BDDA), as the (Z)-isomer ( -BDDA), is a synthetic, nonsteroidal estrogen related to doisynolic acid that was never marketed. It is one of the most potent estrogens known, although it has more recently been characterized as a selective estrogen receptor modulator (SERM). BDDA and other doisynolic acid derivatives display relatively low affinity accompanied by disproportionately high estrogenic potency in vivo, which was eventually determined to be due to transformation into metabolites with greater estrogenic activity. The drug was discovered in 1947 as a degradation product of the reaction of equilenin or dihydroequilenin with potassium hydroxide. It is the seco-analogue of equilenin, while doisynolic acid is the seco-analogue of estrone. These compounds, along with diethylstilbestrol, can be considered to be open-ring analogues of estradiol. The methyl ether of BDDA, doisynoestrol, is also an estrogen, and in contrast to BDDA, has been marketed.

Metenolone acetate chemical compound

Metenolone acetate, or methenolone acetate, sold under the brand names Primobolan and Nibal, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is taken by mouth. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available. A related drug, metenolone enanthate, is given by injection into muscle.

Triphenylchloroethylene

Triphenylchloroethylene, or triphenylchlorethylene, also known as chlorotriphenylethylene or as phenylstilbene chloride, is a synthetic nonsteroidal estrogen of the triphenylethylene group that was marketed in the 1940s for the treatment of menopausal symptoms, vaginal atrophy, lactation suppression, and all other estrogen-indicated conditions.

Allenestrol chemical compound

Allenestrol, or allenoestrol, also known as α,α-dimethyl-β-ethylallenolic acid or as methallenestrilphenol, is a synthetic, nonsteroidal estrogen and a derivative of allenolic acid that was never marketed. A methyl ether of allenestrol, methallenestril (methallenestrol), is also an estrogen, but, in contrast to allenestrol, has been marketed.

References

  1. Negwer M, Scharnow HG (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 1861. ISBN   978-3-527-30247-5. C20H15Br. 1607-57-4. Bromotriphenylethene = Triphenylbromoethylene = Phenylstilbene bromide = 1,1',1"-(1-Bromo-1-ethenyl-2-yli- dene)tris[benzene] (•) S Bromylene, Fenbrostilbenum, Oestronyl, Phenylstilbene bromide, Prostilban, Tribenorm U Synthetic estrogen
  2. Paterson E, Gilbert CW (May 1949). "Metabolism of the oestrogen triphenylbromoethylene". Nature. 163 (4151): 801–802. doi:10.1038/163801a0. PMID   18128458. S2CID   13052481.
  3. Emmens CW (22 October 2013). Hormone Assay. Elsevier Science. pp. 394–. ISBN   978-1-4832-7286-3.
  4. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 183–. ISBN   978-1-4757-2085-3.
  5. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 139–. ISBN   978-3-88763-075-1.