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 | |
| Routes of administration | By mouth |
| Drug class | Selective estrogen receptor modulator |
| ATC code | |
| Pharmacokinetic data | |
| Bioavailability | Good/~100%[1][2] |
| Protein binding | 99.7%[1] |
| Metabolism | Liver (CYP3A4)[5][2] |
| Metabolites | N-Desmethyltoremifene; 4-Hydroxytoremifene; Ospemifene[3][4] |
| Elimination half-life | Toremifene: 3–7 days[1] Metabolites: 4–21 days[2][4][1] |
| Excretion | Feces: 70% (as metabolites)[2] |
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| ECHA InfoCard | 100.125.139 |
| Chemical and physical data | |
| Formula | C26H28ClNO |
| Molar mass | 405.97 g·mol−1 |
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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.[4][6][3] It is taken by mouth.[4]
Side effects of toremifene include hot flashes, sweating, nausea, vomiting, dizziness, vaginal discharge, and vaginal bleeding.[5][7] It can also cause blood clots, irregular heartbeat, cataracts, visual disturbances, elevated liver enzymes, endometrial hyperplasia, and endometrial cancer.[5] High blood calcium levels can occur in women with bone metastases.[5]
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.[5][7] It has estrogenic effects in bone, the liver, and the uterus and antiestrogenic effects in the breasts.[6][8][9][5] 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]
- ^ a b c d Cite error: The named reference
pmid11108432was invoked but never defined (see the help page). - ^ a b c d DeVita Jr VT, Lawrence TS, Rosenberg SA (7 January 2015). DeVita, Hellman, and Rosenberg's Cancer: Principles & Practice of Oncology. Wolters Kluwer Health. pp. 1126–. ISBN 978-1-4698-9455-3.
- ^ a b Chabner BA, Longo DL (7 December 2011). Cancer Chemotherapy and Biotherapy: Principles and Practice. Lippincott Williams & Wilkins. pp. 659–. ISBN 978-1-4511-4820-6.
- ^ a b c d "FARESTON (toremifene citrate) 60 mg Tablets oral administration" (PDF). GTx, Inc. U.S. Food and Drug Administration. March 2011. Archived from the original (PDF) on January 18, 2017.
- ^ a b c d e f Cite error: The named reference
RosenthalBurchum2017was invoked but never defined (see the help page). - ^ a b Miller WR, Ingle JN (8 March 2002). Endocrine Therapy in Breast Cancer. CRC Press. pp. 55–57. ISBN 978-0-203-90983-6.
- ^ a b Cite error: The named reference
SchiffArrillaga2017was invoked but never defined (see the help page). - ^ Cite error: The named reference
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BidlackOmaye2000was invoked but never defined (see the help page). - ^ Cite error: The named reference
DiSaiaCreasman2017was invoked but never defined (see the help page). - ^ "Generic Fareston Availability - Drugs.com". Drugs.com. Retrieved 2019-04-19.