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 a member of the stilbestrol group of nonsteroidal estrogens. TPE is the parent compound of a group of nonsteroidal estrogen receptor ligands. It includes the estrogens chlorotrianisene, desmethylchlorotrianisene,

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 ...

(DBE),

M2613 M2613 is a nonsteroidal estrogen derived from triphenylbromoethylene which was studied in the treatment of breast cancer Breast cancer is cancer that develops from breast tissue. Signs of breast cancer may include a lump in the breast, a ...

triphenylbromoethylene 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 ma ...

triphenylchloroethylene Triphenylchloroethylene (TPCE; brand names Gynosone, Oestrogyl), or triphenylchlorethylene, also known as chlorotriphenylethylene or as phenylstilbene chloride, is a synthetic nonsteroidal estrogen of the triphenylethylene group that was markete ...

triphenyliodoethylene Triphenyliodoethylene (TPIE), also known as iodotriphenylethylene or as phenylstilbene iodide, as well as triphenylvinyl iodide, is a synthetic nonsteroidal estrogen of the triphenylethylene group that is related to triphenylchloroethylene and ...

triphenylmethylethylene Triphenylmethylethylene, also known as methyltriphenylethylene or as triphenylpropene, is a synthetic nonsteroidal estrogen of the triphenylethylene group that is related to triphenylchloroethylene and was never marketed. Along with diethylstil ...

; the

selective estrogen receptor modulator Selective estrogen receptor modulators (SERMs), also known as estrogen receptor agonist/antagonists (ERAAs), are a class of drugs that act on the estrogen receptor (ER). A characteristic that distinguishes these substances from pure ER agonists a ...

s (SERMs)

afimoxifene Afimoxifene, also known as 4-hydroxytamoxifen (4-OHT) and by its tentative brand name TamoGel, is a selective estrogen receptor modulator (SERM) of the triphenylethylene group and an active metabolite of tamoxifen. The drug is under development u ...

brilanestrant Brilanestrant (INN) (developmental code names GDC-0810, ARN-810, RG-6046, RO-7056118) is a nonsteroidal combined selective estrogen receptor modulator (SERM) and selective estrogen receptor degrader (SERD) that was discovered by Aragon Pharmaceu ...

broparestrol Broparestrol () (brand names Acnestrol, Longestrol; former developmental code name LN-107), also known as α-bromo-α,β-diphenyl-β-p-ethylphenylethylene (BDPE), is a synthetic, nonsteroidal selective estrogen receptor modulator (SERM) of the tr ...

, clomifene,

clomifenoxide Clomifenoxide (INN), also known as clomifene ''N''-oxide, is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that is described as an antiestrogen and " gonad stimulant" and was never marketed. It is an ...

, droloxifene, endoxifen, etacstil,

fispemifene Fispemifene (INN, USAN) (developmental code name HM-101) is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that was developed for the treatment of male hypogonadism but was abandoned and never marketed ...

idoxifene Idoxifene (INN, USAN, BAN) (former developmental code names CB-7432, SB-223030), also known as pyrrolidino-4-iodotamoxifen, is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group which was under developmen ...

, miproxifene,

miproxifene phosphate Miproxifene phosphate (former developmental code name TAT-59) is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that was under development in Japan for the treatment of breast cancer but was abandoned a ...

nafoxidine Nafoxidine (; developmental code names U-11,000A) or nafoxidine hydrochloride () is a nonsteroidal selective estrogen receptor modulator (SERM) or partial antiestrogen of the triphenylethylene group that was developed for the treatment of adv ...

ospemifene Ospemifene (brand names Osphena and Senshio produced by Shionogi) is an oral medication indicated for the treatment of dyspareuniapain during sexual intercourseencountered by some women, more often in those who are post-menopausal. Ospemifene is ...

panomifene Panomifene (International Nonproprietary Name, INN; developmental codes GYKI 13504 and EGIS 5650) is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group related to tamoxifen that was under development as an ...

, and toremifene. The antiestrogen ethamoxytriphetol (MER-25) is also closely related, but is technically not a derivative of TPE and is instead a triphenylethanol derivative. The tamoxifen

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

and aromatase inhibitor norendoxifen is also a TPE derivative. In addition to their estrogenic activity, various TPE derivatives like tamoxifen and clomifene have been found to act as protein kinase C inhibitors. The

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 Partn ...

of triphenylethylene for the rat estrogen receptor is about 0.002% relative to estradiol. For comparison, the relative binding affinities of derivatives of triphenylethylene were 1.6% for tamoxifen, 175% for

(4-hydroxytamoxifen), 15% for droloxifene, 1.4% for toremifene (4-chlorotamoxifen), 0.72% for clomifene, and 0.72% for

See also