T0R

Toremifene

Created: 2016-05-04
Last modified:  2016-06-29

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Chemical Details

Formal Charge0
Atom Count57
Chiral Atom Count0
Bond Count59
Aromatic Bond Count18
2D diagram of T0R

Chemical Component Summary

Name Toremifene
Systematic Name (OpenEye OEToolkits)2-[4-[(~{Z})-4-chloranyl-1,2-diphenyl-but-1-enyl]phenoxy]-~{N},~{N}-dimethyl-ethanamine
FormulaC26 H28 Cl N O
Molecular Weight405.96
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01c3cc(C(=C(/CCCl)c1ccccc1)/c2ccccc2)ccc3OCCN(C)C
SMILESCACTVS3.385CN(C)CCOc1ccc(cc1)C(=C(CCCl)c2ccccc2)c3ccccc3
SMILESOpenEye OEToolkits2.0.4CN(C)CCOc1ccc(cc1)C(=C(CCCl)c2ccccc2)c3ccccc3
Canonical SMILESCACTVS3.385 CN(C)CCOc1ccc(cc1)C(=C(/CCCl)c2ccccc2)/c3ccccc3
Canonical SMILESOpenEye OEToolkits2.0.4 CN(C)CCOc1ccc(cc1)/C(=C(/CCCl)\c2ccccc2)/c3ccccc3
InChIInChI1.03 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-
InChIKeyInChI1.03 XFCLJVABOIYOMF-QPLCGJKRSA-N

Drug Info: DrugBank

DrugBank IDDB00539 
NameToremifene
Groups
  • approved
  • investigational
DescriptionToremifene is a selective estrogen receptor modulator (SERM) and a nonsteroidal antiestrogen used to treat estrogen receptor positive breast cancer.[A256923] Like [tamoxifen], toremifene is part of the first-generation triphenylethylene derivative chemical class of SERMs.[A256928] Toremifene possesses tissue-specific actions: it has estrogenic (agonist) activity on the cardiovascular system and on bone tissue and it has weak estrogenic effects on uterine tissue, however, it also has antiestrogenic (estrogen-antagonist) activity on breast tissue.[A256923]
Synonyms
  • Toremifenum
  • Toremifene
  • Toremifeno
  • Toremifene citrate
Brand Names
  • Fareston
  • Toremifene Citrate
IndicationFor 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.
Categories
  • Anti-Estrogens
  • Antineoplastic Agents
  • Antineoplastic Agents, Hormonal
  • Antineoplastic and Immunomodulating Agents
  • Benzene Derivatives
ATC-CodeL02BA02
CAS number89778-26-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Estrogen receptor alphaMTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPA...unknownmodulator
Sex hormone-binding globulinMESRGPLATSRLLLLLLLLLLRHTRQGWALRPVLPTQSAHDPPAVHLSNG...unknown
Cytochrome P450 1A1MLFPISMSATEFLLASVIFCLVFWVIRASRPQVPKGLKNPPGPWGWPLIG...unknownsubstrate
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor
P-glycoprotein 1MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1655
PubChem 3005573
ChEMBL CHEMBL1655
ChEBI CHEBI:9635
CCDC/CSD QICMEU