Chlorotrianisene

Chlorotrianisene
Clinical data
Trade namesTace, Estregur, Anisene, Clorotrisin, Merbentyl, Triagen, others
Other namesCTA; Trianisylchloroethylene; tri-p-Anisylchloroethylene; TACE; tris(p-Methoxyphenyl)-chloroethylene; NSC-10108
AHFS/Drugs.comMultum Consumer Information
Routes of
administration		By mouth[1][2]
Drug classNonsteroidal estrogen
ATC code
Pharmacokinetic data
MetabolismMono-O-demethylation (liver CYP450)[3][4]
MetabolitesDesmethylchlorotrianisene[3][4]
Identifiers
IUPAC name
  • 1,1',1''-(2-chloroethene-1,1,2-triyl)tris(4-methoxybenzene); 11-chloro-4,13-dimethoxy-12-(p-methoxyphenyl)stilbene
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.008.472
Chemical and physical data
FormulaC23H21ClO3
Molar mass380.87 g·mol−1
3D model (JSmol)
SMILES
  • COc1ccc(C(Cl)=C(c2ccc(OC)cc2)c2ccc(OC)cc2)cc1
InChI
  • InChI=1S/C23H21ClO3/c1-25-19-10-4-16(5-11-19)22(17-6-12-20(26-2)13-7-17)23(24)18-8-14-21(27-3)15-9-18/h4-15H,1-3H3 Y
  • Key:BFPSDSIWYFKGBC-UHFFFAOYSA-N Y
  (verify)

Chlorotrianisene (CTA), also known as tri-p-anisylchloroethylene (TACE) and sold under the brand name Tace among others, is a nonsteroidal estrogen related to diethylstilbestrol (DES) which was previously used in the treatment of menopausal symptoms and estrogen deficiency in women and prostate cancer in men, among other indications, but has since been discontinued and is now no longer available.[5][6][7][1][8] It is taken by mouth.[1][2]

CTA is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol.[7][1][9][10] It is a high-efficacy partial estrogen and shows some properties of a selective estrogen receptor modulator, with predominantly estrogenic activity but also some antiestrogenic activity.[11][12] CTA itself is inactive and is a prodrug in the body.[2][13]

CTA was introduced for medical use in 1952.[14] It has been marketed in the United States and Europe.[14][6] However, it has since been discontinued and is no longer available in any country.[1][15]

  1. ^ a b c d e Sweetman SC, ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 2085. ISBN 978-0-85369-840-1.
  2. ^ a b c Cite error: The named reference Meikle2003 was invoked but never defined (see the help page).
  3. ^ a b Ruenitz PC, Toledo MM (August 1981). "Chemical and biochemical characteristics of O-demethylation of chlorotrianisene in the rat". Biochem. Pharmacol. 30 (16): 2203–7. doi:10.1016/0006-2952(81)90088-5. PMID 7295335.
  4. ^ a b Jordan VC (1986). Estrogen/antiestrogen Action and Breast Cancer Therapy. Univ of Wisconsin Press. p. 212. ISBN 978-0-299-10480-1.
  5. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 263–. ISBN 978-1-4757-2085-3.
  6. ^ a b Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 219–. ISBN 978-3-88763-075-1.
  7. ^ a b Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 73–. ISBN 978-94-011-4439-1.
  8. ^ Cox RL, Crawford ED (December 1995). "Estrogens in the treatment of prostate cancer". The Journal of Urology. 154 (6): 1991–8. doi:10.1016/S0022-5347(01)66670-9. PMID 7500443.
  9. ^ Luniwal A, Jetson R, Erhardt P (2012). "Selective Estrogen Receptor Modulators". In Fischer J, Ganellin CR, Rotella DP (eds.). Analogue-Based Drug Discovery III. pp. 165–185. doi:10.1002/9783527651085.ch7. ISBN 9783527651085.
  10. ^ Jordan VC, Lieberman ME (September 1984). "Estrogen-stimulated prolactin synthesis in vitro. Classification of agonist, partial agonist, and antagonist actions based on structure". Molecular Pharmacology. 26 (2): 279–85. PMID 6541293.
  11. ^ Cite error: The named reference FischerGanellin2012 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Sneader2005 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference Hadden2013 was invoked but never defined (see the help page).
  14. ^ a b Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference Micromedex was invoked but never defined (see the help page).
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