Lapatinib (CED0002000)

Record Information
Version1.0
Creation Date2016-05-22 05:52:42 UTC
Update Date2026-08-22 08:48:21 UTC
Accession NumberCHEM019167
Identification
Common NameLapatinib
ClassSmall Molecule
Description
Lapatinib is an organic compound with the chemical formula C29H26ClFN4O4S. Lapatinib belongs to the benzodiazines, a subclass of diazanaphthalenes within the organic compounds. With an average molecular weight of 581.06 g/mol, Lapatinib is a heavy molecule. This compound acts as an antagonist or inhibitor of three protein targets: the Epidermal growth factor receptor (EGFR), Receptor tyrosine-protein kinase erbB-2 (ERBB2), and Eukaryotic elongation factor 2 kinase (EEF2K). Regarding its presence and application, Lapatinib is found in or released from six recorded sources. These include healthcare, pharmaceuticals, and veterinary products, specifically as antineoplastic agents. Additionally, it is associated with electrical and electronic equipment, such as television systems, line transmission systems, and electric hearing aids, as well as household cleaning and consumer products, including pipe accessories and non-electric simulated smoking devices. The recorded route of exposure for this compound is oral.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GW 572016ChEBI
N-(3-Chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)-2-furanyl)-4-quinazolinamineChEBI
N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)-2-furyl]-4-quinazolinamineChEBI
TykerbChEBI
N-(3-Chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulphonyl)ethyl)amino)methyl)-2-furanyl)-4-quinazolinamineGenerator
N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulphonyl)ethyl]amino}methyl)-2-furyl]-4-quinazolinamineGenerator
FMMHMDB
GW572016HMDB
Lapatinib ditosylateHMDB
Lapatinib tosilate hydrateHMDB
N-(3-Chloro-4-(((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-methylsulfonyl)ethyl)amino)methyl) -2-furyl)-4-quinazolinamineHMDB
Chemical FormulaC29H26ClFN4O4S
Average Molecular Mass581.058 g/mol
Monoisotopic Mass580.135 g/mol
CAS Registry Number231277-92-2
IUPAC NameN-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-(5-{[(2-methanesulfonylethyl)amino]methyl}furan-2-yl)quinazolin-4-amine
Traditional Namelapatinib
SMILESCS(=O)(=O)CCNCC1=CC=C(O1)C1=CC2=C(C=C1)N=CN=C2NC1=CC(Cl)=C(OCC2=CC(F)=CC=C2)C=C1
InChI IdentifierInChI=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 KeyBCFGMOOMADDAQU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentQuinazolinamines
Alternative Parents
Substituents
  • Quinazolinamine
  • Phenoxy compound
  • Aniline or substituted anilines
  • Phenol ether
  • Aralkylamine
  • Halobenzene
  • Fluorobenzene
  • Chlorobenzene
  • Aminopyrimidine
  • Alkyl aryl ether
  • Imidolactam
  • Benzenoid
  • Pyrimidine
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Aryl chloride
  • Heteroaromatic compound
  • Sulfonyl
  • Sulfone
  • Furan
  • Oxacycle
  • Azacycle
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.022 g/LALOGPS
logP5.18ALOGPS
logP4.64ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)15.99ChemAxon
pKa (Strongest Basic)7.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area106.35 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity152.42 m³·mol⁻¹ChemAxon
Polarizability61.19 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0pb9-6920550000-7316e856fd5ec8e04f07Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lr-0009070000-0d55ba750eaa2fb12020Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lr-0009070000-0d55ba750eaa2fb12020Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-0649800000-87742edfe3489dab4ac8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0002090000-49e599088394c442e60bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0009020000-1e12983abcdd66482af3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0000090000-f080a7f403cbfd88c590Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0000090000-e1a1377443b8f411d997Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0009000000-0b1867dee117396c1949Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0000090000-d725217276a0f9a7e793Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0100290000-631c05424fb5cef349dbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a5i-1701890000-169201e0014b0f4031fcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-6922200000-21ac033aa8e06fb42b19Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-5100190000-854bae0cfc77e5929d1eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9100110000-7b6eac51a2b17a8a0213Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9100000000-16d9d0819f6dca47cd5cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0000290000-c15d2a8b4702b6befdbdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0001490000-80635a463a3e3328f17bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pbj-2119400000-10638e7b757119205a69Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0000090000-9043926cc3ed698dc68eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03fr-1109630000-a046bbec44d7c31559d0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0059-9204010000-e84077eb1512ec5949baNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
3961.0Log mg/kg[2200:7000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
Pathways
3 pathways
Lapatinib Action Pathway
Lapatinib Action Pathway
Lapatinib Drug Metabolism Action Pathway
Lapatinib Drug Metabolism Action Pathway
Lapatinib Predicted Metabolism Pathway
Lapatinib Predicted Metabolism Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)4.20386
Receptor tyrosine-protein kinase erbB-2 structureClick to view 3D structureReceptor tyrosine-protein kinase erbB-2P04626HumansPredicted (SEA)1.55698
Tyrosine-protein kinase ABL1 structureClick to view 3D structureTyrosine-protein kinase ABL1P00519HumansPredicted (SEA)2.80257
Platelet-derived growth factor receptor beta structureClick to view 3D structurePlatelet-derived growth factor receptor betaP09619HumansPredicted (SEA)1.08989
Insulin receptor structureClick to view 3D structureInsulin receptorP06213HumansPredicted (SEA)1.79053
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)0.778492
Serine/threonine-protein kinase PLK1 structureClick to view 3D structureSerine/threonine-protein kinase PLK1P53350HumansPredicted (SEA)2.10193
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)2.64687
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)2.56902
Histone deacetylase 8 structureClick to view 3D structureHistone deacetylase 8Q9BY41HumansPredicted (SEA)3.11397
Histone deacetylase 3 structureClick to view 3D structureHistone deacetylase 3O15379HumansPredicted (SEA)3.26967
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)71.3877
Receptor tyrosine-protein kinase erbB-4 structureClick to view 3D structureReceptor tyrosine-protein kinase erbB-4Q15303HumansPredicted (SEA)23.5883
Aurora kinase A structureClick to view 3D structureAurora kinase AO14965HumansPredicted (SEA)31.4511
Angiopoietin-1 receptor structureClick to view 3D structureAngiopoietin-1 receptorQ02763HumansPredicted (SEA)11.8331
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)72.7112
Hepatocyte growth factor receptor structureClick to view 3D structureHepatocyte growth factor receptorP08581HumansPredicted (SEA)42.0386
Tyrosine-protein kinase JAK2 structureClick to view 3D structureTyrosine-protein kinase JAK2O60674HumansPredicted (SEA)51.7697
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)26.2352
Tyrosine-protein kinase SYK structureClick to view 3D structureTyrosine-protein kinase SYKP43405HumansPredicted (SEA)31.0618
Mast/stem cell growth factor receptor Kit structureClick to view 3D structureMast/stem cell growth factor receptor KitP10721HumansPredicted (SEA)49.59
Platelet-derived growth factor receptor alpha structureClick to view 3D structurePlatelet-derived growth factor receptor alphaP16234HumansPredicted (SEA)26.1573
Insulin-like growth factor 1 receptor structureClick to view 3D structureInsulin-like growth factor 1 receptorP08069HumansPredicted (SEA)39.236
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)39.4696
Fibroblast growth factor receptor 1 structureClick to view 3D structureFibroblast growth factor receptor 1P11362HumansPredicted (SEA)49.045
Concentrations
Not Available
External Links
DrugBank IDDB01259
HMDB IDHMDB0015388
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLapatinib
Chemspider ID181006
ChEBI ID49603
PubChem Compound ID208908
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Burris HA 3rd: Dual kinase inhibition in the treatment of breast cancer: initial experience with the EGFR/ErbB-2 inhibitor lapatinib. Oncologist. 2004;9 Suppl 3:10-5.
2. Burris HA 3rd, Hurwitz HI, Dees EC, Dowlati A, Blackwell KL, O'Neil B, Marcom PK, Ellis MJ, Overmoyer B, Jones SF, Harris JL, Smith DA, Koch KM, Stead A, Mangum S, Spector NL: Phase I safety, pharmacokinetics, and clinical activity study of lapatinib (GW572016), a reversible dual inhibitor of epidermal growth factor receptor tyrosine kinases, in heavily pretreated patients with metastatic carcinomas. J Clin Oncol. 2005 Aug 10;23(23):5305-13. Epub 2005 Jun 13.
3. Nelson MH, Dolder CR: Lapatinib: a novel dual tyrosine kinase inhibitor with activity in solid tumors. Ann Pharmacother. 2006 Feb;40(2):261-9. Epub 2006 Jan 17.
4. Johnston SR, Leary A: Lapatinib: a novel EGFR/HER2 tyrosine kinase inhibitor for cancer. Drugs Today (Barc). 2006 Jul;42(7):441-53.
5. Geyer CE, Forster J, Lindquist D, Chan S, Romieu CG, Pienkowski T, Jagiello-Gruszfeld A, Crown J, Chan A, Kaufman B, Skarlos D, Campone M, Davidson N, Berger M, Oliva C, Rubin SD, Stein S, Cameron D: Lapatinib plus capecitabine for HER2-positive advanced breast cancer. N Engl J Med. 2006 Dec 28;355(26):2733-43.
6. Medina PJ, Goodin S: Lapatinib: a dual inhibitor of human epidermal growth factor receptor tyrosine kinases. Clin Ther. 2008 Aug;30(8):1426-47. doi: 10.1016/j.clinthera.2008.08.008.
7. Tevaarwerk AJ, Kolesar JM: Lapatinib: a small-molecule inhibitor of epidermal growth factor receptor and human epidermal growth factor receptor-2 tyrosine kinases used in the treatment of breast cancer. Clin Ther. 2009;31 Pt 2:2332-48. doi: 10.1016/j.clinthera.2009.11.029.