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Triphenylchloroethylene

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Triphenylchloroethylene
Clinical data

Trade names	Gynosone, Oestrogyl
Other names	TPCE; Triphenylchlorethylene; Chlorotriphenylethylene; Phenylstilbene chloride
Drug class	Nonsteroidal estrogen
Identifiers
IUPAC name (1-chloro-2,2-diphenylethenyl)benzene
CAS Number	18084-97-4^Y
PubChem CID	87450
ChemSpider	78884
UNII	AV6NM693EG
CompTox Dashboard (EPA)	DTXSID80171020
Chemical and physical data
Formula	C₂₀H₁₅Cl
Molar mass	290.79 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Cl)C3=CC=CC=C3
InChI InChI=1S/C20H15Cl/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:QEQFTTCZLHLKFX-UHFFFAOYSA-N

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 marketed in the 1940s for the treatment of menopausal symptoms, vaginal atrophy, lactation suppression, and all other estrogen-indicated conditions.^[1]^[2]^[3]

The estrogenic effects of triphenylethylene, the parent compound of triphenylchloroethylene, were discovered in 1937.^[4] Triphenylchloroethylene was first reported in 1938 and was found to have 20 to 100 times the estrogenic activity of the relatively weak triphenylethylene, a potentiation of effect that was afforded by its halogen substituent.^[2]^[5] The drug has a relatively long duration of action when administered via subcutaneous injection but a duration similar to that of diethylstilbestrolorestradiol benzoate when administered orally.^[2]^[6]^[7] Along with diethylstilbestrol and triphenylmethylethylene, triphenylchloroethylene was studied in 1944 by Sir Alexander Haddow for the treatment of breast cancer and was found to be significantly effective, and this is historically notable in that it was the first time that high-dose estrogens were found to be effective in the treatment of breast cancer.^[8]^[9]

Chlorotrianisene, or tri-p-anisylchloroethylene (TACE), is a potent marketed estrogen and a derivative of triphenylchloroethylene in which each of the three phenyl rings has been substituted with a 4-methoxy group.^[5]^[10] Estrobin, or DBE, is a related, never-marketed estrogen in which there is a bromine in place of the chlorine and two of the three phenyl rings have ethoxy groups.^[5] Broparestrol, or BDPE is a marketed selective estrogen receptor modulator (SERM) that has a bromine in place of the chlorine of triphenylchloroethylene and a 4-ethyl group on one of the phenyl rings. The SERM clomifene is also a derivative of triphenylchloroethylene.^[11]

References[edit]

^ Negwer M, Scharnow HG (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. pp. 1861–1862. ISBN 978-3-527-30247-5. C20H15Cl 18084-97-4 Chlorotriphenylethene = Triphenylchloroethylene = Phenylstilbene chloride = 1,1',1"-(1-Chloro-1-ethenyl-2-ylidene)tris[benzene] (•) S Gynosone, Oestrogyl, Phenylstilbene chloride U Synthetic estrogen

^ ^a ^b ^c Emmens CW (July 1947). "Halogen-substituted oestrogens related to triphenylethylene". The Journal of Endocrinology. 5 (3): 170–173. doi:10.1677/joe.0.0050170. PMID 20259249.

^ ""Gynosone" A New Synthetic Oestrogen" (PDF). Advertisement. Proc R Soc Med. 39 (11). Sep 1946. PMC 2181944.

^ Li JJ (3 April 2009). "Genesis of Statins". Triumph of the Heart: The Story of Statins. Oxford University Press, USA. pp. 33–. ISBN 978-0-19-532357-3.

^ ^a ^b ^c Solmssen UV (December 1945). "Synthetic estrogens and the relation between their structure and their activity". Chemical Reviews. 37 (3): 481–598. doi:10.1021/cr60118a004. PMID 21013428.

^ Jordon VC, Koch R, Lieberman ME (1986). "Structure-Activity Relationships of Nonsteroidal Estrogens and Antiestrogens". In Jordan VC (ed.). Estrogen/antiestrogen Action and Breast Cancer Therapy. University of Wisconsin Press. pp. 23–. ISBN 978-0-299-10480-1.

^ Maximov PY, McDaniel RE, Jordan VC (23 July 2013). "Discovery and Pharmacology of Nonsteroidal Estrogens and Antiestrogens". Tamoxifen: Pioneering Medicine in Breast Cancer. Springer Science & Business Media. pp. 4–. ISBN 978-3-0348-0664-0.

^ Lewis-Wambi J, Jordan VC (27 May 2013). "Diethylstilbestrol: A Tragedy in Reproductive Endocrinology But a Pioneering Cancer Treatment". In Jordan VC (ed.). Estrogen Action, Selective Estrogen Receptor Modulators and Women's Health: Progress and Promise. World Scientific. pp. 42–. ISBN 978-1-84816-959-3.

^ Wagener DJ (13 July 2009). "The history of the hormonal treatment of cancer". The History of Oncology. Bohn Stafleu van Loghum. pp. 189–. ISBN 978-90-313-6143-4.

^ Lisi F (2006). "Adjunctions to Clomiphene Citrate". In Allahbadia G (ed.). Contemporary Perspectives on Assisted Reproductive Technology. Elsevier India. pp. 18–. ISBN 978-81-8147-782-8.

^ Shoham Z, Howles CM (27 June 2012). "Drugs used for ovarian stimulation: Clomiphene citrate, aromatase inhibitors, metformin, gonadotropins, gonadotropin-releasing hormone analogs and recombinant gonadotropins". In Gardner DK, Weissman A, Howles CM, Shoham Z (eds.). Textbook of Assisted Reproductive Techniques Fourth Edition: Volume 2: Clinical Perspectives. CRC Press. pp. 51–. ISBN 978-1-84184-972-0.

Estrogens and antiestrogens

Estrogens

ER agonists

Steroidal: Alfatradiol
Certain androgens/anabolic steroids (e.g., testosterone, testosterone esters, methyltestosterone, metandienone, nandrolone esters) (via estrogenic metabolites)
Certain progestins (e.g., norethisterone, noretynodrel, etynodiol diacetate, tibolone)
Clomestrone
Cloxestradiol acetate
Conjugated estriol
Conjugated estrogens
Epiestriol
Epimestrol
Esterified estrogens
Estetrol^†
Estradiol
Estradiol esters (e.g., estradiol acetate, estradiol benzoate, estradiol cypionate, estradiol enanthate, estradiol undecylate, estradiol valerate, polyestradiol phosphate, estradiol ester mixtures (Climacteron))
Estramustine phosphate
Estriol
Estriol esters (e.g., estriol succinate, polyestriol phosphate)
Estrogenic substances
Estrone
Estrone esters
- Estrone sulfate
- Estropipate (piperazine estrone sulfate)
Ethinylestradiol^#
- Ethinylestradiol sulfonate
Hydroxyestrone diacetate
Mestranol
Methylestradiol
Moxestrol
Nilestriol
Prasterone (dehydroepiandrosterone; DHEA)
- Prasterone enanthate
- Prasterone sulfate
Promestriene
Quinestradol
Quinestrol

Progonadotropins

Antiandrogens (e.g., bicalutamide)
GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
Gonadotropins (e.g., FSHTooltip follicle-stimulating hormone, LHTooltip luteinizing hormone)

Antiestrogens

ERTooltip Estrogen receptor antagonists (incl. SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)	Acolbifene^† Anordrin Bazedoxifene Broparestrol Clomifene^# Cyclofenil Enclomifene^† Epitiostanol Lasofoxifene Mepitiostane Ormeloxifene Ospemifene Raloxifene Tamoxifen^# Toremifene Exclusively antagonistic: Elacestrant Fulvestrant Noncompetitive inhibitors: Trilostane
Aromatase inhibitors	First-generation: Aminoglutethimide Testolactone Second-generation: Fadrozole Formestane Third-generation: Anastrozole Exemestane Letrozole
Antigonadotropins	Androgens/anabolic steroids (e.g., testosterone, testosterone esters, nandrolone esters, oxandrolone, fluoxymesterone) D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride) GnRH agonists (e.g., leuprorelin, goserelin) GnRH antagonists (e.g., cetrorelix, elagolix) Progestogens (e.g., chlormadinone acetate, cyproterone acetate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone acetate, megestrol acetate)
Others	Mixed mechanism of action: Danazol Gestrinone Androstenedione immunogens: Androvax (androstenedione albumin) Ovandrotone albumin (Fecundin)