FMM

N-{3-CHLORO-4-[(3-FLUOROBENZYL)OXY]PHENYL}-6-[5-({[2-(METHYLSULFONYL)ETHYL]AMINO}METHYL)-2-FURYL]-4-QUINAZOLINAMINE

Created: 2004-10-04
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count66
Chiral Atom Count0
Bond Count70
Aromatic Bond Count29
2D diagram of FMM
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Chemical Component Summary

NameN-{3-CHLORO-4-[(3-FLUOROBENZYL)OXY]PHENYL}-6-[5-({[2-(METHYLSULFONYL)ETHYL]AMINO}METHYL)-2-FURYL]-4-QUINAZOLINAMINE
Systematic Name (OpenEye OEToolkits)N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine
FormulaC29 H26 Cl F N4 O4 S
Molecular Weight581.058
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04Fc1cccc(c1)COc2ccc(cc2Cl)Nc5ncnc4c5cc(c3oc(cc3)CNCCS(=O)(=O)C)cc4
SMILESCACTVS3.341C[S](=O)(=O)CCNCc1oc(cc1)c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2
SMILESOpenEye OEToolkits1.5.0CS(=O)(=O)CCNCc1ccc(o1)c2ccc3c(c2)c(ncn3)Nc4ccc(c(c4)Cl)OCc5cccc(c5)F
Canonical SMILESCACTVS3.341 C[S](=O)(=O)CCNCc1oc(cc1)c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2
Canonical SMILESOpenEye OEToolkits1.5.0 CS(=O)(=O)CCNCc1ccc(o1)c2ccc3c(c2)c(ncn3)Nc4ccc(c(c4)Cl)OCc5cccc(c5)F
InChIInChI1.03 InChI=1S/C29H26ClFN4O4S/c1-40(36,37)12-11-32-16-23-7-10-27(39-23)20-5-8-26-24(14-20)29(34-18-33-26)35-22-6-9-28(25(30)15-22)38-17-19-3-2-4-21(31)13-19/h2-10,13-15,18,32H,11-12,16-17H2,1H3,(H,33,34,35)
InChIKeyInChI1.03 BCFGMOOMADDAQU-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB01259 
NameLapatinib
Groups
  • approved
  • investigational
DescriptionLapatinib is an anti-cancer drug developed by GlaxoSmithKline (GSK) as a treatment for solid tumours such as breast and lung cancer. It was approved by the FDA on March 13, 2007, for use in patients with advanced metastatic breast cancer in conjunction with the chemotherapy drug capecitabine. Lapatinib is a human epidermal growth factor receptor type 2 (HER2/ERBB2) and epidermal growth factor receptor (HER1/EGFR/ERBB1) tyrosine kinases inhibitor. It binds to the intracellular phosphorylation domain to prevent receptor autophosphorylation upon ligand binding.
Synonyms
  • N-(3-chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)-2-furanyl)-4-quinazolinamine
  • Lapatinib
  • Lapatinib ditosylate
Brand Names
  • Tyverb
  • Tykerb
  • Lapatinib
IndicationIndicated in combination with capecitabine for the treatment of patients with advanced or metastatic breast cancer whose tumors overexpress the human epidermal receptor type 2 (HER2) protein and who have received prior therapy including an anthracycline, a taxane, and trastuzumab.
Categories
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • Cytochrome P-450 CYP2C19 Substrates
  • Cytochrome P-450 CYP2C8 Inhibitors
  • Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
ATC-CodeL01EH01
CAS number231277-92-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Epidermal growth factor receptorMRPSGTAGAALLALLAALCPASRALEEKKVCQGTSNKLTQLGTFEDHFLS...unknownantagonist
Receptor tyrosine-protein kinase erbB-2MELAALCRWGLLLALLPPGAASTQVCTGTDMKLRLPASPETHLDMLRHLY...unknownantagonist
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknownsubstrate
Cytochrome P450 2C8MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...unknownsubstrate,inhibitor
View More
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 CHEMBL554
PubChem 208908
ChEMBL CHEMBL554
ChEBI CHEBI:49603
CCDC/CSD OVAYOB