U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C26H28ClNO
Molecular Weight 405.9605
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TOREMIFENE

SMILES

CN(C)CCOc1ccc(cc1)/C(=C(/CCCl)\c2ccccc2)/c3ccccc3

InChI

InChIKey=XFCLJVABOIYOMF-QPLCGJKRSA-N
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-

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020497s006lbl.pdf

Toremifene is an antineoplastic hormonal agent primarily used in the treatment of advanced breast cancer. Toremifene is a nonsteroidal agent that has demonstrated potent antiestrogenic properties in animal test systems. The antiestrogenic effects may be related to its ability to compete with estrogen for binding sites in target tissues such as breast. Toremifene inhibits the induction of rat mammary carcinoma induced by dimethylbenzanthracene (DMBA) and causes the regression of already established DMBA-induced tumors. In this rat model, Toremifene appears to exert its antitumor effects by binding the estrogen receptors. In cytosols derived from human breast adenocarcinomas, Toremifene competes with estradiol for estrogen receptor protein. Toremifene is a nonsteroidal triphenylethylene derivative. Toremifene binds to estrogen receptors and may exert estrogenic, antiestrogenic, or both activities, depending upon the duration of treatment, animal species, gender, target organ, or endpoint selected. The antitumor effect of toremifene in breast cancer is believed to be mainly due to its antiestrogenic effects, in other words, its ability to compete with estrogen for binding sites in the cancer, blocking the growth-stimulating effects of estrogen in the tumor. Toremifene may also inhibit tumor growth through other mechanisms, such as induction of apoptosis, regulation of oncogene expression, and growth factors. Toremifene is used for the treatment of metastatic breast cancer in postmenopausal women with estrogen receptor-positive or receptor-unknown tumors. Toremifene is currently under investigation as a preventative agent for prostate cancer in men with high-grade prostatic intraepithelial neoplasia and no evidence of prostate cancer. Toremifene is marketed in the United States under the brand name Fareston.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FARESTON

Approved Use

FARESTON® is an estrogen agonist/antagonist indicated for the treatment of metastatic breast cancer in postmenopausal women with estrogen-receptor positive or unknown tumors.

Launch Date

8.647776E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
414 ng/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOREMIFENE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
722 ng/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOREMIFENE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
28.4 μg × h/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOREMIFENE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
34.1 μg × h/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOREMIFENE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.2 day
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOREMIFENE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
99 h
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TOREMIFENE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
400 mg/m2 1 times / day steady, oral
MTD
Dose: 400 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 400 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 5
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 5
Sources: Page: 175
DLT: Nausea and vomiting, Dizziness...
Other AEs: Sweating, Peripheral edema...
Dose limiting toxicities:
Nausea and vomiting (grade 1-4, 5 patients)
Dizziness (grade 1-4, 4 patients)
Other AEs:
Sweating (grade 1-4, 3 patients)
Peripheral edema (grade 1-4, 3 patients)
Vaginal discharge (grade 1-4, 0%)
Hot flushes (grade 1-4, 2 patients)
Sources: Page: 175
200 mg/m2 1 times / day steady, oral
Recommended
Dose: 200 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 200 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 8
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 8
Sources: Page: 175
Other AEs: Nausea and vomiting, Dizziness...
Other AEs:
Nausea and vomiting (grade 1-4, 7 patients)
Dizziness (grade 1-4, 2 patients)
Sweating (grade 1-4, 2 patients)
Peripheral edema (grade 1-4, 2 patients)
Vaginal discharge (grade 1-4, 2 patients)
Hot flushes (grade 1-4, 1 patient)
Sources: Page: 175
300 mg/m2 1 times / day steady, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 300 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 6
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 6
Sources: Page: 175
Other AEs: Nausea and vomiting, Dizziness...
Other AEs:
Nausea and vomiting (grade 1-4, 6 patients)
Dizziness (grade 1-4, 4 patients)
Sweating (grade 1-4, 3 patients)
Peripheral edema (grade 1-4, 4 patients)
Vaginal discharge (grade 1-4, 3 patients)
Hot flushes (grade 1-4, 4 patients)
Sources: Page: 175
AEs

AEs

AESignificanceDosePopulation
Vaginal discharge grade 1-4, 0%
400 mg/m2 1 times / day steady, oral
MTD
Dose: 400 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 400 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 5
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 5
Sources: Page: 175
Hot flushes grade 1-4, 2 patients
400 mg/m2 1 times / day steady, oral
MTD
Dose: 400 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 400 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 5
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 5
Sources: Page: 175
Peripheral edema grade 1-4, 3 patients
400 mg/m2 1 times / day steady, oral
MTD
Dose: 400 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 400 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 5
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 5
Sources: Page: 175
Sweating grade 1-4, 3 patients
400 mg/m2 1 times / day steady, oral
MTD
Dose: 400 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 400 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 5
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 5
Sources: Page: 175
Dizziness grade 1-4, 4 patients
DLT
400 mg/m2 1 times / day steady, oral
MTD
Dose: 400 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 400 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 5
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 5
Sources: Page: 175
Nausea and vomiting grade 1-4, 5 patients
DLT
400 mg/m2 1 times / day steady, oral
MTD
Dose: 400 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 400 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 5
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 5
Sources: Page: 175
Hot flushes grade 1-4, 1 patient
200 mg/m2 1 times / day steady, oral
Recommended
Dose: 200 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 200 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 8
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 8
Sources: Page: 175
Dizziness grade 1-4, 2 patients
200 mg/m2 1 times / day steady, oral
Recommended
Dose: 200 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 200 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 8
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 8
Sources: Page: 175
Peripheral edema grade 1-4, 2 patients
200 mg/m2 1 times / day steady, oral
Recommended
Dose: 200 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 200 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 8
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 8
Sources: Page: 175
Sweating grade 1-4, 2 patients
200 mg/m2 1 times / day steady, oral
Recommended
Dose: 200 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 200 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 8
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 8
Sources: Page: 175
Vaginal discharge grade 1-4, 2 patients
200 mg/m2 1 times / day steady, oral
Recommended
Dose: 200 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 200 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 8
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 8
Sources: Page: 175
Nausea and vomiting grade 1-4, 7 patients
200 mg/m2 1 times / day steady, oral
Recommended
Dose: 200 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 200 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 8
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 8
Sources: Page: 175
Sweating grade 1-4, 3 patients
300 mg/m2 1 times / day steady, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 300 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 6
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 6
Sources: Page: 175
Vaginal discharge grade 1-4, 3 patients
300 mg/m2 1 times / day steady, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 300 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 6
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 6
Sources: Page: 175
Dizziness grade 1-4, 4 patients
300 mg/m2 1 times / day steady, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 300 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 6
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 6
Sources: Page: 175
Hot flushes grade 1-4, 4 patients
300 mg/m2 1 times / day steady, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 300 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 6
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 6
Sources: Page: 175
Peripheral edema grade 1-4, 4 patients
300 mg/m2 1 times / day steady, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 300 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 6
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 6
Sources: Page: 175
Nausea and vomiting grade 1-4, 6 patients
300 mg/m2 1 times / day steady, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: steady
Dose: 300 mg/m2, 1 times / day
Sources: Page: 175
unhealthy, 38 - 79 years
n = 6
Health Status: unhealthy
Condition: metastatic breast cancer
Age Group: 38 - 79 years
Sex: F
Population Size: 6
Sources: Page: 175
PubMed

PubMed

TitleDatePubMed
Comparison of the effects of tamoxifen and toremifene on liver and kidney tumor promotion in female rats.
1995 Nov
A two-year dietary carcinogenicity study of the antiestrogen toremifene in Sprague-Dawley rats.
1996 Nov
Structure-activity relationships for triphenylethylene antiestrogens on hepatic phase-I and phase-II enzyme expression.
1998 Aug 1
Toremifene-induced fatty liver and NASH in breast cancer patients with breast-conservation treatment.
2000 Dec
[A case of locally recurrent breast cancer in which phlebothrombosis of the right leg after hormonal therapy using a high dose of toremifene citrate].
2002 Jan
Effect of anti-estrogens on the androgen receptor activity and cell proliferation in prostate cancer cells.
2004 Dec
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Drug resistance in chemotherapy for breast cancer.
2005 Nov
Estrogen receptors as therapeutic targets in breast cancer.
2006
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
Patents

Sample Use Guides

60 mg once daily, orally
Route of Administration: Oral
In Vitro Use Guide
Treatment of the human breast cancer cell line MCF-7 with 7.5 uM toremifene for 3 days caused approximately 60% of the cells to exhibit morphologic characteristics typical of cells undergoing apoptosis.
Name Type Language
TOREMIFENE
EMA EPAR   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
TOREMIFENE [WHO-DD]
Common Name English
TOREMIFENE [IARC]
Common Name English
TOREMIFENE [VANDF]
Common Name English
TOREMIFENE [INN]
Common Name English
CHLORTAMOXIFEN
Common Name English
GTX-006
Code English
TOREMIPHENE
Common Name English
TOREMIFENE [MI]
Common Name English
ACAPODENE
Common Name English
ETHANAMINE, 2-(4-((1Z)-4-CHLORO-1,2-DIPHENYL-1-BUTEN-1-YL)PHENOXY)-N,N-DIMETHYL-
Systematic Name English
J33.157K
Code English
FARESTONE
Brand Name English
TOREMIFENE [EMA EPAR]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 75393
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
EMA ASSESSMENT REPORTS FARESTON(AUTHORIZED: BREAST NEOPLASMS)
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
NDF-RT N0000175826
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
WHO-VATC QL02BA02
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
FDA ORPHAN DRUG 60291
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
LIVERTOX 983
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
NCI_THESAURUS C1821
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
WHO-ATC L02BA02
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
NDF-RT N0000000168
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
Code System Code Type Description
PUBCHEM
3005573
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY
FDA UNII
7NFE54O27T
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY
MERCK INDEX
M10979
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY Merck Index
MESH
D017312
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY
EPA CompTox
89778-26-7
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY
NCI_THESAURUS
C1256
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY
INN
5698
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY
EVMPD
SUB11197MIG
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY
WIKIPEDIA
TOREMIFENE
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY
DRUG BANK
DB00539
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY
DRUG CENTRAL
2709
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY
RXCUI
38409
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL1655
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY
CAS
89778-26-7
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY
IUPHAR
4325
Created by admin on Sat Jun 26 00:15:36 UTC 2021 , Edited by admin on Sat Jun 26 00:15:36 UTC 2021
PRIMARY