lapatinib   Click here for help

GtoPdb Ligand ID: 5692

Synonyms: FMM | GW 572016 | GW572016 | Tykerb® | Tyverb®
Approved drug PDB Ligand
lapatinib is an approved drug (FDA (2007), EMA (2008))
Compound class: Synthetic organic
Comment: Lapatinib is a Type-1.5 kinase inhibitor and was first approved by the US FDA in 2007.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 114.73
Molecular weight 580.13
XLogP 5.41
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES Fc1cccc(c1)COc1ccc(cc1Cl)Nc1ncnc2c1cc(cc2)c1ccc(o1)CNCCS(=O)(=O)C
Isomeric SMILES Fc1cccc(c1)COc1ccc(cc1Cl)Nc1ncnc2c1cc(cc2)c1ccc(o1)CNCCS(=O)(=O)C
InChI 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)
InChI Key BCFGMOOMADDAQU-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2007), EMA (2008))
IUPAC Name Click here for help
N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-(5-{[(2-methanesulfonylethyl)amino]methyl}furan-2-yl)quinazolin-4-amine
International Nonproprietary Names Click here for help
INN number INN
8378 lapatinib
Synonyms Click here for help
FMM | GW 572016 | GW572016 | Tykerb® | Tyverb®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-1216521
Reactome Reaction Reactome logo R-HSA-9652264, R-HSA-9665412, R-HSA-9665121, R-HSA-1220610, R-HSA-9665284, R-HSA-9665702
Other databases
CAS Registry No. 231277-92-2
ChEMBL Ligand CHEMBL554
DrugBank Ligand DB01259
DrugCentral Ligand 1548
GtoPdb PubChem SID 178102319
PubChem CID 208908
RCSB PDB Ligand FMM
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Wikipedia Lapatinib

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Tocris
Lapatinib
Cat. No. 6811