Chlorotrianisene

Chlorotrianisene
Clinical data
Trade names	Tace, Estregur, Anisene, Clorotrisin, Merbentyl, Triagen, others
Other names	CTA; Trianisylchloroethylene; tri-p-Anisylchloroethylene; TACE; tris(p-Methoxyphenyl)-chloroethylene; NSC-10108
AHFS/Drugs.com	Multum Consumer Information
Routes of; administration	By mouth
Drug class	Nonsteroidal estrogen
ATC code	G03CA06 (WHO) ;
Pharmacokinetic data
Metabolism	Mono-O-demethylation (liver CYP450)
Metabolites	Desmethylchlorotrianisene
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	569-57-3 ;
PubChem CID	11289;
IUPHAR/BPS	7146;
DrugBank	DB00269 ;
ChemSpider	10815 ;
UNII	6V5034L121;
KEGG	D00269 ;
ChEBI	CHEBI:3641 ;
ChEMBL	ChEMBL1200761 ;
CompTox Dashboard (EPA)	DTXSID1021299 ;
ECHA InfoCard	100.008.472
Chemical and physical data
Formula	C23H21ClO3
Molar mass	380.87 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:BFPSDSIWYFKGBC-UHFFFAOYSA-N ;
	(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. It is taken by mouth.

CTA is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol. 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. CTA itself is inactive and is a prodrug in the body.

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

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