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Desmethylchlorotrianisene

Clinical data
Other names	DMCTA
Drug class	Nonsteroidal estrogen
Identifiers
IUPAC name (EZ)-4-phenol
PubChem CID	53325692
ChemSpider	25047392
Chemical and physical data
Formula	C20H15ClO3
Molar mass	338.79 g·mol
3D model (JSmol)	Interactive image
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). It is a 1:1 mixture of cis and trans isomers. DMCTA is produced from CTA via mono-O-demethylation catalyzed by cytochrome P450 enzymes in the liver. CTA is thought to act as a long-lasting prodrug of DMCTA.

References

1. ^ 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. ^ 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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