Desmethylchlorotrianisene

Desmethylchlorotrianisene
Clinical data
Other namesDMCTA
Drug classNonsteroidal estrogen
Identifiers
IUPAC name
  • (EZ)-4-[2-Chloro-1,2-bis(4-hydroxyphenyl)ethenyl]phenol
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC20H15ClO3
Molar mass338.79 g·mol−1
3D model (JSmol)
SMILES
  • OC1=CC=C(/C(C2=CC=C(OC)C=C2)=C(Cl)/C3=CC=C(OC)C=C3)C=C1
InChI
  • InChI=1S/C20H15ClO3/c21-20(15-5-11-18(24)12-6-15)19(13-1-7-16(22)8-2-13)14-3-9-17(23)10-4-14/h1-12,22-24H
  • Key:XQRLRQNJWROVPF-UHFFFAOYSA-N

Desmethylchlorotrianisene (DMCTA) is a nonsteroidal estrogen which is thought to be the major active metabolite of chlorotrianisene (CTA; TACE).[1][2] It is a 1:1 mixture of cis and trans isomers.[1][2] DMCTA is produced from CTA via mono-O-demethylation catalyzed by cytochrome P450 enzymes in the liver.[1][2] CTA is thought to act as a long-lasting prodrug of DMCTA.[1]

References

  1. 1 2 3 4 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.
  2. 1 2 3 Virgil Craig Jordan (1986). Estrogen/antiestrogen Action and Breast Cancer Therapy. Univ of Wisconsin Press. p. 212. ISBN 978-0-299-10480-1.



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