Toremifene

Toremifene
Clinical data
Pronunciation/ˈtɔːrəmɪfiːn/
Trade namesFareston, others
Other names(Z)-Toremifene; 4-Chlorotamoxifen; 4-CT; Acapodene; CCRIS-8745; FC-1157; FC-1157a; GTx-006; NK-622; NSC-613680
AHFS/Drugs.comMonograph
MedlinePlusa608003
License data
Routes of
administration		By mouth
Drug classSelective estrogen receptor modulator
ATC code
Pharmacokinetic data
BioavailabilityGood/~100%[1][2]
Protein binding99.7%[1]
MetabolismLiver (CYP3A4)[5][2]
MetabolitesN-Desmethyltoremifene; 4-Hydroxytoremifene; Ospemifene[3][4]
Elimination half-lifeToremifene: 3–7 days[1]
Metabolites: 4–21 days[2][4][1]
ExcretionFeces: 70% (as metabolites)[2]
Identifiers
  • 2-[4-[(1Z)-4-Chloro-1,2-diphenyl-but-1-en-1-yl]phenoxy]-N,N-dimethylethanamine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.125.139 Edit this at Wikidata
Chemical and physical data
FormulaC26H28ClNO
Molar mass405.97 g·mol−1
3D model (JSmol)
  • ClCCC(/c1ccccc1)=C(/c2ccc(OCCN(C)C)cc2)c3ccccc3
  • 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- checkY
  • Key:XFCLJVABOIYOMF-QPLCGJKRSA-N checkY
  (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.[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]

  1. ^ a b c d Cite error: The named reference pmid11108432 was invoked but never defined (see the help page).
  2. ^ 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.
  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.
  4. ^ a b c d "FARESTON (toremifene citrate) 60 mg Tablets oral administration" (PDF). GTx, Inc. U.S. Food and Drug Administration. March 2011.
  5. ^ a b c d e f Cite error: The named reference RosenthalBurchum2017 was invoked but never defined (see the help page).
  6. ^ 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.
  7. ^ a b Cite error: The named reference SchiffArrillaga2017 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference MorrowJordan2003 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference ScholarlyEditions2013 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference CanoAlsina2006 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference SilvaZurrida2005 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference BidlackOmaye2000 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference DiSaiaCreasman2017 was invoked but never defined (see the help page).
  14. ^ "Generic Fareston Availability - Drugs.com". Drugs.com. Retrieved 2019-04-19.