Toremifene
Chemical compound / From Wikipedia, the free encyclopedia
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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.[5][6][4] It is taken by mouth.[5]
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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 |
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Routes of administration | By mouth |
Drug class | Selective estrogen receptor modulator |
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Bioavailability | Good/~100%[1][2] |
Protein binding | 99.7%[1] |
Metabolism | Liver (CYP3A4)[3][2] |
Metabolites | N-Desmethyltoremifene; 4-Hydroxytoremifene; Ospemifene[4][5] |
Elimination half-life | Toremifene: 3–7 days[1] Metabolites: 4–21 days[2][5][1] |
Excretion | Feces: 70% (as metabolites)[2] |
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ECHA InfoCard | 100.125.139 |
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Formula | C26H28ClNO |
Molar mass | 405.97 g·mol−1 |
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Side effects of toremifene include hot flashes, sweating, nausea, vomiting, dizziness, vaginal discharge, and vaginal bleeding.[3][7] It can also cause blood clots, irregular heartbeat, cataracts, visual disturbances, elevated liver enzymes, endometrial hyperplasia, and endometrial cancer.[3] High blood calcium levels can occur in women with bone metastases.[3]
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.[3][7] It has estrogenic effects in bone, the liver, and the uterus and antiestrogenic effects in the breasts.[6][8][9][3] It is a triphenylethylene derivative and is closely related to tamoxifen.[10]
Toremifene was introduced for medical use in 1997.[11][12] It was the first antiestrogen to be introduced since tamoxifen in 1978.[13] It is available as a generic medication in the United States.[14]