Triphenyliodoethylene - Misplaced Pages

Chemical compound Pharmaceutical compound

Triphenyliodoethylene
Clinical data

Other names	TPIE; Iodotriphenylethylene; Phenylstilbene iodide; Triphenylvinyl iodide
Drug class	Nonsteroidal estrogen
Identifiers
IUPAC name (1-iodo-2,2-diphenylethenyl)benzene
PubChem CID	12139089
CompTox Dashboard (EPA)	DTXSID201337054
Chemical and physical data
Formula	C₂₀H₁₅I
Molar mass	382.244 g·mol
3D model (JSmol)	Interactive image
SMILES C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)I)C3=CC=CC=C3
InChI InChI=1S/C20H15I/c21-20(18-14-8-3-9-15-18)19(16-10-4-1-5-11-16)17-12-6-2-7-13-17/h1-15H Key:DVJCEGLTPUEWNX-UHFFFAOYSA-N

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 triphenylbromoethylene and was never marketed.

References

Tadros W (1947). "Synthetic oestrogens related to triphenylethylene". Proceedings of the XIth International Congress of Pure and Applied Chemistry: Chemistry in relation to medicine and theropeutics [sic], chemistry in relation to fuel, power and transport. Hepworth. p. 149. In fact the cestrogenic activity of either triphenylbromoethylene or triphenyliodoethylene (J. 3d. Robson, A. Schonberg and H. A. Fahim)(3) (Table 1) compares with that of triphenylchloroethylene. A True Oestrogen and A Pro-oestrogen.
Burton TF (1952). British Abstracts. Bureau of Abstracts. p. 549. Roughly quantitative data are reported for the antagonism between oestrogens (oestradiol, stilboestrol, doisynolic acid, allenolic acid, and triphenyliodoethylene) and progesterone, methyltestosterone, and testosterone propionate given
Egyptian Veterinary Medical Association (1966). Annual Veterinary Congress, Proceedings. L'Institut Francais d'Archéologie Orientale. p. 392. But the synthetic oestrogens tested e.g. stilboesterol, triphenyliodoethylene, diosynolic acid and allenolic acid produce constant inhibition of the uterine motility.

ERTooltip Estrogen receptor

Agonists

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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