(Z)-Toremifene

Also known as Farestone®, FC-1157a, Toremifenum, Toremifeno, Toremifene, 2-{4-[(1Z)-4-Chloro-1,2-diphenyl-1-buten-1-yl]phenoxy}-N,N-dimethylethanamine, toremifene

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.

Chemical data

Formula: C26H28ClNO
Molecular weight: 406 g/mol
IUPAC name: 2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine
SMILES: CN(C)CCOC1=CC=C(C=C1)/C(=C(/CCCl)\C2=CC=CC=C2)/C3=CC=CC=C3
InChIKey: XFCLJVABOIYOMF-QPLCGJKRSA-N
XLogP: 7.2
Polar surface area: 12.5 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1996
Admin. routes: oral
Indications: neoplasm, prostate intraepithelial neoplasia, breast neoplasm, bone fracture

via ChEMBL · EBI

Research

14 papers

(131)I-Labeled [Z]-2-[4-(1,2-diphenyl-1-di-butenyl)-phenoxy]-N,N-dimethylethanamine.2004
Mass spectrometric characterization of toremifene metabolites in human urine by liquid chromatography-tandem mass spectrometry with different scan modes.The Analyst · 2011
Toremifene interacts with and destabilizes the Ebola virus glycoprotein.Nature · 2016
Mass spectrometric characterization of urinary toremifene metabolites for doping control analyses.Journal of chromatography. A · 2011
Toremifene metabolism in rat, mouse and human liver microsomes: identification of alpha-hydroxytoremifene by LC-MS.Biomedical chromatography : BMC · 2002

via PubMed

Wikidata facts

Mass: 405.186
Has use: medication

Show 10 more facts

subject has role: selective estrogen-receptor modulators
chemical formula: C₂₆H₂₈ClNO
significant drug interaction: clarithromycin
route of administration: oral administration
medical condition treated: breast cancer
canonical SMILES: CN(C)CCOC1=CC=C(C=C1)C(=C(CCCl)C2=CC=CC=C2)C3=CC=CC=C3
isomeric SMILES: CN(C)CCOC1=CC=C(C=C1)/C(=C(/CCCl)\C2=CC=CC=C2)/C3=CC=CC=C3
World Health Organisation international non-proprietary name: toremifene
defined daily dose: 60
Commons category: Toremifene

Sources (5)

via Wikidata · CC0

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Encyclopedic overview

22 sections

Contents

Medical uses
Available forms
Side effects
Interactions
Pharmacology
Pharmacodynamics
Pharmacokinetics
Absorption
Distribution
Metabolism
Elimination
Chemistry
History
Society and culture
Generic names
Brand names
Availability
Research
Phase III Trial Results
References
Further reading
External links

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.

Excerpted from Wikipedia’s “(Z)-Toremifene” article, available under the CC BY-SA 4.0 licence.

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