Toremifene

Toremifene
Clinical data
Pronunciation	/ˈtɔːrəmɪfiːn/
Trade names	Fareston, others
Other names	(Z)-Toremifene; 4-Chlorotamoxifen; 4-CT; Acapodene; CCRIS-8745; FC-1157; FC-1157a; GTx-006; NK-622; NSC-613680
AHFS/Drugs.com	Monograph
MedlinePlus	a608003
License data	EU EMA: by INN;
Routes of; administration	By mouth
Drug class	Selective estrogen receptor modulator
ATC code	L02BA02 (WHO) ;
Pharmacokinetic data
Bioavailability	Good/~100%
Protein binding	99.7%
Metabolism	Liver (CYP3A4)
Metabolites	N-Desmethyltoremifene; 4-Hydroxytoremifene; Ospemifene
Elimination half-life	Toremifene: 3–7 days; Metabolites: 4–21 days
Excretion	Feces: 70% (as metabolites)
Identifiers
	IUPAC name 2-[4-[(1Z)-4-Chloro-1,2-diphenyl-but-1-en-1-yl]phenoxy]-N,N-dimethylethanamine;
CAS Number	89778-26-7 ; 89778-27-8 (citrate);
PubChem CID	3005573;
IUPHAR/BPS	4325;
DrugBank	DB00539 ;
ChemSpider	2275722 ;
UNII	7NFE54O27T;
KEGG	D08620 ;
ChEBI	CHEBI:9635 ;
ChEMBL	ChEMBL1655 ;
PDB ligand	T0R (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID3023689 ;
ECHA InfoCard	100.125.139
Chemical and physical data
Formula	C26H28ClNO
Molar mass	405.97 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES ClCCC(/c1ccccc1)=C(/c2ccc(OCCN(C)C)cc2)c3ccccc3;
	InChI InChI=1S/C26H28ClNO/c1-28(2)19-20-29-24-15-13-23(14-16-24)26(22-11-7-4-8-12-22)25(17-18-27)21-9-5-3-6-10-21/h3-16H,17-20H2,1-2H3/b26-25- ; Key:XFCLJVABOIYOMF-QPLCGJKRSA-N ;
	(verify)

Toremifene, sold under the brand name Fareston among others, is a medication which is used in the treatment of advanced breast cancer in postmenopausal women. It is taken by mouth.

Side effects of toremifene include hot flashes, sweating, nausea, vomiting, dizziness, vaginal discharge, and vaginal bleeding. It can also cause blood clots, irregular heartbeat, cataracts, visual disturbances, elevated liver enzymes, endometrial hyperplasia, and endometrial cancer. High blood calcium levels can occur in women with bone metastases.

The medication is a selective estrogen receptor modulator (SERM) and hence is a mixed agonist–antagonist of the estrogen receptor (ER), the biological target of estrogens like estradiol. It has estrogenic effects in bone, the liver, and the uterus and antiestrogenic effects in the breasts. It is a triphenylethylene derivative and is closely related to tamoxifen.

Toremifene was introduced for medical use in 1997. It was the first antiestrogen to be introduced since tamoxifen in 1978. It is available as a generic medication in the United States.

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