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Synthetic form of estrogen
Triphenylchloroethylene
Trade names Gynosone, Oestrogyl Other names TPCE; Triphenylchlorethylene; Chlorotriphenylethylene; Phenylstilbene chloride
Drug class
Nonsteroidal estrogen
(1-chloro-2,2-diphenylethenyl)benzene
CAS Number
PubChem
CID
ChemSpider
UNII
Formula C 20 H 15 Cl
Molar mass 290.79 g·mol−1 3D model (
JSmol )
C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Cl)C3=CC=CC=C3
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
diethylstilbestrol or
estradiol 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]
See also
References
^ 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 .
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