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Identification
NameLapatinib
Accession NumberDB01259  (DB02584)
TypeSmall Molecule
GroupsApproved, 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 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.
Structure
Thumb
Synonyms
FMM
GW 572016
Lapatinib tosilate hydrate
N-(3-chloro-4-((3-Fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)-2-furanyl)-4-quinazolinamine
N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)-2-furyl]-4-quinazolinamine
Tykerb
External Identifiers
  • GW 572016
  • GW572016
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
TykerbTablet250 mg/1OralGlaxo Smith Kline Llc2007-03-16Not applicableUs
TykerbTablet250 mgOralNovartis Pharmaceuticals Canada Inc2009-06-05Not applicableCanada
TykerbTablet250 mg/1OralNovartis Pharmaceuticals Corporation2016-08-03Not applicableUs
TyverbTablet, film coated250 mgOralNovartis Europharm Limited2008-06-10Not applicableEu
TyverbTablet, film coated250 mgOralNovartis Europharm Limited2008-06-10Not applicableEu
TyverbTablet, film coated250 mgOralNovartis Europharm Limited2008-06-10Not applicableEu
TyverbTablet, film coated250 mgOralNovartis Europharm Limited2008-06-10Not applicableEu
TyverbTablet, film coated250 mgOralNovartis Europharm Limited2008-06-10Not applicableEu
TyverbTablet, film coated250 mgOralNovartis Europharm Limited2008-06-10Not applicableEu
TyverbTablet, film coated250 mgOralNovartis Europharm Limited2008-06-10Not applicableEu
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
TycerbNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Lapatinib ditosylate
388082-78-8
Thumb
  • InChI Key: XNRVGTHNYCNCFF-UHFFFAOYSA-N
  • Monoisotopic Mass: 942.1841276
  • Average Mass: 943.47
DBSALT001785
Categories
UNII0VUA21238F
CAS number231277-92-2
WeightAverage: 581.058
Monoisotopic: 580.134731942
Chemical FormulaC29H26ClFN4O4S
InChI KeyBCFGMOOMADDAQU-UHFFFAOYSA-N
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)
IUPAC Name
N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-(5-{[(2-methanesulfonylethyl)amino]methyl}furan-2-yl)quinazolin-4-amine
SMILES
CS(=O)(=O)CCNCC1=CC=C(O1)C1=CC2=C(C=C1)N=CN=C2NC1=CC(Cl)=C(OCC2=CC(F)=CC=C2)C=C1
Pharmacology
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 trastuzuma.
Structured Indications
PharmacodynamicsLapatinib is a small molecule and a member of the 4-anilinoquinazoline class of kinase inhibitors. An anti-cancer drug, lapatinib was 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.
Mechanism of actionLapatinib is a 4-anilinoquinazoline kinase inhibitor of the intracellular tyrosine kinase domains of both epidermal growth factor receptor (HER1/EGFR/ERBB1) and human epidermal growth factor receptor type 2 (HER2/ERBB2)with a dissociation half-life of ≥300 minutes. Lapatinib inhibits ERBB-driven tumor cell growth in vitro and in various animal models. An additive effect was demonstrated in an in vitro study when lapatinib and 5-florouracil (the active metabolite of capecitabine) were used in combination in the 4 tumor cell lines tested. The growth inhibitory effects of lapatinib were evaluated in trastuzumab-conditioned cell lines. Lapatinib retained significant activity against breast cancer cell lines selected for long-term growth in trastuzumab-containing medium in vitro. These in vitro findings suggest non-cross-resistance between these two agents.
TargetKindPharmacological actionActionsOrganismUniProt ID
Epidermal growth factor receptorProteinyes
antagonist
HumanP00533 details
Receptor tyrosine-protein kinase erbB-2Proteinyes
antagonist
HumanP04626 details
Related Articles
AbsorptionAbsorption following oral administration of lapatinib is incomplete and variable.
Volume of distributionNot Available
Protein bindingHighly bound (>99%) to albumin and alpha-1 acid glycoprotein
Metabolism

Lapatinib undergoes extensive metabolism, primarily by CYP3A4 and CYP3A5, with minor contributions from CYP2C19 and CYP2C8 to a variety of oxidated metabolites, none of which accounts for more than 14% of the dose recovered in the feces or 10% of lapatinib concentration in plasma.

Route of eliminationLapatinib undergoes extensive metabolism, primarily by CYP3A4 and CYP3A5, with minor contributions from CYP2C19 and CYP2C8 to a variety of oxidated metabolites, none of which accounts for more than 14% of the dose recovered in the feces or 10% of lapatinib concentration in plasma.
Half lifeSingle-dose terminal half life: 14.2 hours Effective multiple-dose half life: 24 hours
ClearanceNot Available
ToxicityThere has been a report of one patient who took 3,000 mg of lapatinib for 10 days. This patient had grade 3 diarrhea and vomiting on day 10.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Lapatinib can be increased when it is combined with Abiraterone.Approved
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Lapatinib.Approved
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Lapatinib.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Lapatinib.Approved
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Lapatinib.Approved, Vet Approved
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Lapatinib.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Lapatinib.Experimental
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Lapatinib.Approved, Investigational
AlmotriptanThe metabolism of Almotriptan can be decreased when combined with Lapatinib.Approved, Investigational
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Lapatinib.Approved, Investigational
AminophenazoneThe metabolism of Aminophenazone can be decreased when combined with Lapatinib.Approved, Withdrawn
AmiodaroneThe serum concentration of Lapatinib can be increased when it is combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Lapatinib.Approved
AmodiaquineThe metabolism of Amodiaquine can be decreased when combined with Lapatinib.Approved
AmprenavirThe metabolism of Amprenavir can be decreased when combined with Lapatinib.Approved
AnagrelideLapatinib may increase the QTc-prolonging activities of Anagrelide.Approved
AntipyrineThe metabolism of Antipyrine can be decreased when combined with Lapatinib.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Lapatinib.Investigational
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Lapatinib.Approved
AprepitantThe serum concentration of Lapatinib can be increased when it is combined with Aprepitant.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Lapatinib.Approved, Investigational
ArmodafinilThe metabolism of Lapatinib can be decreased when combined with Armodafinil.Approved, Investigational
Arsenic trioxideLapatinib may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherLapatinib may increase the QTc-prolonging activities of Artemether.Approved
AsenapineLapatinib may increase the QTc-prolonging activities of Asenapine.Approved
AtazanavirThe serum concentration of Lapatinib can be increased when it is combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Atenolol can be increased when it is combined with Lapatinib.Approved
AtomoxetineThe metabolism of Lapatinib can be decreased when combined with Atomoxetine.Approved
AtorvastatinThe metabolism of Atorvastatin can be decreased when combined with Lapatinib.Approved
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Lapatinib.Approved, Investigational
AzelastineThe metabolism of Azelastine can be decreased when combined with Lapatinib.Approved
AzithromycinLapatinib may increase the QTc-prolonging activities of Azithromycin.Approved
BedaquilineLapatinib may increase the QTc-prolonging activities of Bedaquiline.Approved
Benzyl alcoholThe metabolism of Benzyl alcohol can be decreased when combined with Lapatinib.Approved
BeraprostThe metabolism of Beraprost can be decreased when combined with Lapatinib.Investigational
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Lapatinib.Approved, Vet Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Lapatinib.Approved, Investigational
BexaroteneThe serum concentration of Lapatinib can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe serum concentration of Lapatinib can be increased when it is combined with Boceprevir.Approved
BortezomibThe metabolism of Lapatinib can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Lapatinib can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Lapatinib.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Lapatinib.Approved
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Lapatinib.Approved, Investigational
BrompheniramineThe metabolism of Brompheniramine can be decreased when combined with Lapatinib.Approved
BuprenorphineThe metabolism of Buprenorphine can be decreased when combined with Lapatinib.Approved, Illicit, Investigational, Vet Approved
BupropionThe metabolism of Bupropion can be decreased when combined with Lapatinib.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Lapatinib.Approved
CaffeineThe serum concentration of Caffeine can be increased when it is combined with Lapatinib.Approved
CamptothecinThe serum concentration of Camptothecin can be increased when it is combined with Lapatinib.Experimental
CanagliflozinThe serum concentration of Canagliflozin can be increased when it is combined with Lapatinib.Approved
CarbamazepineThe serum concentration of Lapatinib can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarbinoxamineThe metabolism of Carbinoxamine can be decreased when combined with Lapatinib.Approved
CarfilzomibThe serum concentration of Carfilzomib can be increased when it is combined with Lapatinib.Approved
CelecoxibThe metabolism of Lapatinib can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Lapatinib can be increased when it is combined with Ceritinib.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Lapatinib.Withdrawn
ChloramphenicolThe metabolism of Lapatinib can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChloroquineLapatinib may increase the QTc-prolonging activities of Chloroquine.Approved, Vet Approved
ChlorpromazineLapatinib may increase the QTc-prolonging activities of Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Lapatinib can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe serum concentration of Cimetidine can be increased when it is combined with Lapatinib.Approved
CiprofloxacinLapatinib may increase the QTc-prolonging activities of Ciprofloxacin.Approved, Investigational
CisaprideLapatinib may increase the QTc-prolonging activities of Cisapride.Approved, Investigational, Withdrawn
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with Lapatinib.Approved
CitalopramLapatinib may increase the QTc-prolonging activities of Citalopram.Approved
ClarithromycinThe serum concentration of Lapatinib can be increased when it is combined with Clarithromycin.Approved
ClemastineThe metabolism of Lapatinib can be decreased when combined with Clemastine.Approved
ClobazamThe serum concentration of Clobazam can be increased when it is combined with Lapatinib.Approved, Illicit
ClomifeneThe serum concentration of Clomifene can be increased when it is combined with Lapatinib.Approved, Investigational
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Lapatinib.Approved
ClopidogrelThe metabolism of Lapatinib can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe metabolism of Lapatinib can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineLapatinib may increase the QTc-prolonging activities of Clozapine.Approved
CobicistatThe serum concentration of Lapatinib can be increased when it is combined with Cobicistat.Approved
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Lapatinib.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Lapatinib.Approved
ConivaptanThe serum concentration of Lapatinib can be increased when it is combined with Conivaptan.Approved, Investigational
Conjugated Equine EstrogensThe serum concentration of Conjugated Equine Estrogens can be increased when it is combined with Lapatinib.Approved
CrizotinibLapatinib may increase the QTc-prolonging activities of Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Lapatinib.Approved, Investigational
CyclosporineThe metabolism of Lapatinib can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Lapatinib.Approved
DabrafenibThe serum concentration of Lapatinib can be decreased when it is combined with Dabrafenib.Approved
DactinomycinThe serum concentration of Dactinomycin can be increased when it is combined with Lapatinib.Approved
DapagliflozinThe serum concentration of Dapagliflozin can be increased when it is combined with Lapatinib.Approved
DapsoneThe metabolism of Dapsone can be decreased when combined with Lapatinib.Approved, Investigational
DarunavirThe serum concentration of Lapatinib can be increased when it is combined with Darunavir.Approved
DasabuvirThe metabolism of Dasabuvir can be decreased when combined with Lapatinib.Approved
DasatinibThe serum concentration of Lapatinib can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Daunorubicin can be increased when it is combined with Lapatinib.Approved
DebrisoquinThe serum concentration of Debrisoquin can be increased when it is combined with Lapatinib.Approved
DeferasiroxThe serum concentration of Lapatinib can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Lapatinib can be decreased when combined with Delavirdine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Lapatinib.Approved
DexamethasoneThe serum concentration of Lapatinib can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextromethorphanThe metabolism of Dextromethorphan can be decreased when combined with Lapatinib.Approved
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Lapatinib.Approved, Illicit, Vet Approved
DiclofenacThe metabolism of Diclofenac can be decreased when combined with Lapatinib.Approved, Vet Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be increased when it is combined with Lapatinib.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Lapatinib.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Lapatinib.Approved
DihydroergotamineThe metabolism of Lapatinib can be decreased when combined with Dihydroergotamine.Approved
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be increased when it is combined with Lapatinib.Illicit
DiltiazemThe metabolism of Lapatinib can be decreased when combined with Diltiazem.Approved
DipyridamoleThe serum concentration of Dipyridamole can be increased when it is combined with Lapatinib.Approved
DisopyramideLapatinib may increase the QTc-prolonging activities of Disopyramide.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Lapatinib.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Lapatinib.Approved
DolasetronLapatinib may increase the QTc-prolonging activities of Dolasetron.Approved
DomperidoneLapatinib may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Lapatinib.Approved, Investigational
DoxycyclineThe metabolism of Lapatinib can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneLapatinib may increase the QTc-prolonging activities of Dronedarone.Approved
DroperidolLapatinib may increase the QTc-prolonging activities of Droperidol.Approved, Vet Approved
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Lapatinib.Approved
EfavirenzThe serum concentration of Lapatinib can be decreased when it is combined with Efavirenz.Approved, Investigational
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Lapatinib.Approved, Investigational
EliglustatLapatinib may increase the QTc-prolonging activities of Eliglustat.Approved
EltrombopagThe metabolism of Eltrombopag can be decreased when combined with Lapatinib.Approved
EnzalutamideThe serum concentration of Lapatinib can be decreased when it is combined with Enzalutamide.Approved
EpinastineThe serum concentration of Epinastine can be increased when it is combined with Lapatinib.Approved, Investigational
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Lapatinib.Approved, Investigational
ErythromycinLapatinib may increase the QTc-prolonging activities of Erythromycin.Approved, Vet Approved
EscitalopramLapatinib may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
Eslicarbazepine acetateThe serum concentration of Lapatinib can be decreased when it is combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Lapatinib can be decreased when combined with Esomeprazole.Approved, Investigational
EstradiolThe serum concentration of Estradiol can be increased when it is combined with Lapatinib.Approved, Investigational, Vet Approved
EstriolThe serum concentration of Estriol can be increased when it is combined with Lapatinib.Approved, Vet Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Lapatinib.Approved
EszopicloneThe metabolism of Eszopiclone can be decreased when combined with Lapatinib.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Lapatinib.Approved
EtoposideThe serum concentration of Etoposide can be increased when it is combined with Lapatinib.Approved
EtravirineThe serum concentration of Lapatinib can be decreased when it is combined with Etravirine.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Lapatinib.Approved
EzetimibeThe serum concentration of Ezetimibe can be increased when it is combined with Lapatinib.Approved
FelodipineThe metabolism of Lapatinib can be decreased when combined with Felodipine.Approved, Investigational
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Lapatinib.Approved
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Lapatinib.Approved
FidaxomicinThe serum concentration of Fidaxomicin can be increased when it is combined with Lapatinib.Approved
FlecainideLapatinib may increase the QTc-prolonging activities of Flecainide.Approved, Withdrawn
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Lapatinib.Approved
FluconazoleThe metabolism of Lapatinib can be decreased when combined with Fluconazole.Approved
FluorouracilThe metabolism of Fluorouracil can be decreased when combined with Lapatinib.Approved
FluoxetineLapatinib may increase the QTc-prolonging activities of Fluoxetine.Approved, Vet Approved
FlupentixolLapatinib may increase the QTc-prolonging activities of Flupentixol.Approved, Withdrawn
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Lapatinib.Approved
FluvastatinThe metabolism of Fluvastatin can be decreased when combined with Lapatinib.Approved
FluvoxamineThe metabolism of Lapatinib can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Lapatinib can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Lapatinib can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of Lapatinib can be decreased when it is combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Lapatinib can be increased when it is combined with Fusidic Acid.Approved
Gadobenic acidLapatinib may increase the QTc-prolonging activities of Gadobenic acid.Approved
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Lapatinib.Approved, Investigational
GemcitabineThe serum concentration of Gemcitabine can be increased when it is combined with Lapatinib.Approved
GemfibrozilThe metabolism of Lapatinib can be decreased when combined with Gemfibrozil.Approved
GemifloxacinLapatinib may increase the QTc-prolonging activities of Gemifloxacin.Approved, Investigational
GoserelinLapatinib may increase the QTc-prolonging activities of Goserelin.Approved
GranisetronLapatinib may increase the QTc-prolonging activities of Granisetron.Approved, Investigational
GrazoprevirThe serum concentration of Grazoprevir can be increased when it is combined with Lapatinib.Approved
GrepafloxacinThe serum concentration of Grepafloxacin can be increased when it is combined with Lapatinib.Withdrawn
HalofantrineThe metabolism of Halofantrine can be decreased when combined with Lapatinib.Approved
HaloperidolLapatinib may increase the QTc-prolonging activities of Haloperidol.Approved
HydrocodoneThe serum concentration of Hydrocodone can be increased when it is combined with Lapatinib.Approved, Illicit
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Lapatinib.Approved, Vet Approved
IbuprofenThe serum concentration of Ibuprofen can be increased when it is combined with Lapatinib.Approved
IbutilideLapatinib may increase the QTc-prolonging activities of Ibutilide.Approved
IdelalisibThe serum concentration of Lapatinib can be increased when it is combined with Idelalisib.Approved
IfosfamideThe metabolism of Ifosfamide can be decreased when combined with Lapatinib.Approved
IloperidoneLapatinib may increase the QTc-prolonging activities of Iloperidone.Approved
ImatinibThe metabolism of Lapatinib can be decreased when combined with Imatinib.Approved
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Lapatinib.Approved
IndacaterolThe serum concentration of Indacaterol can be increased when it is combined with Lapatinib.Approved
IndinavirThe serum concentration of Lapatinib can be increased when it is combined with Indinavir.Approved
IndomethacinThe serum concentration of Indomethacin can be increased when it is combined with Lapatinib.Approved, Investigational
IrbesartanThe metabolism of Lapatinib can be decreased when combined with Irbesartan.Approved, Investigational
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Lapatinib.Approved, Investigational
IsavuconazoniumThe metabolism of Lapatinib can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Lapatinib can be decreased when combined with Isoniazid.Approved
IsradipineThe metabolism of Lapatinib can be decreased when combined with Isradipine.Approved
ItraconazoleThe serum concentration of Lapatinib can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Lapatinib can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Ivermectin can be increased when it is combined with Lapatinib.Approved, Vet Approved
IxazomibThe metabolism of Ixazomib can be decreased when combined with Lapatinib.Approved
KetamineThe metabolism of Ketamine can be decreased when combined with Lapatinib.Approved, Vet Approved
KetazolamThe serum concentration of Ketazolam can be increased when it is combined with Lapatinib.Approved
KetobemidoneThe metabolism of Ketobemidone can be decreased when combined with Lapatinib.Approved
KetoconazoleThe serum concentration of Lapatinib can be increased when it is combined with Ketoconazole.Approved, Investigational
LamivudineThe serum concentration of Lamivudine can be increased when it is combined with Lapatinib.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be increased when it is combined with Lapatinib.Approved, Investigational
LansoprazoleThe serum concentration of Lansoprazole can be increased when it is combined with Lapatinib.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Lapatinib.Approved
LenalidomideThe serum concentration of Lenalidomide can be increased when it is combined with Lapatinib.Approved
LenvatinibLapatinib may increase the QTc-prolonging activities of Lenvatinib.Approved
LeuprolideLapatinib may increase the QTc-prolonging activities of Leuprolide.Approved, Investigational
LevetiracetamThe serum concentration of Levetiracetam can be increased when it is combined with Lapatinib.Approved, Investigational
LevofloxacinLapatinib may increase the QTc-prolonging activities of Levofloxacin.Approved, Investigational
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Lapatinib.Approved
LicofeloneThe metabolism of Licofelone can be decreased when combined with Lapatinib.Investigational
LidocaineThe metabolism of Lidocaine can be decreased when combined with Lapatinib.Approved, Vet Approved
LinagliptinThe serum concentration of Linagliptin can be increased when it is combined with Lapatinib.Approved
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Lapatinib.Approved
LoperamideThe serum concentration of Loperamide can be increased when it is combined with Lapatinib.Approved
LopinavirThe serum concentration of Lapatinib can be increased when it is combined with Lopinavir.Approved
LoratadineThe metabolism of Loratadine can be decreased when combined with Lapatinib.Approved
LosartanThe serum concentration of Losartan can be increased when it is combined with Lapatinib.Approved
LovastatinThe metabolism of Lapatinib can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Lapatinib can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Lapatinib can be decreased when it is combined with Lumacaftor.Approved
LumefantrineLapatinib may increase the QTc-prolonging activities of Lumefantrine.Approved
MannitolThe serum concentration of Mannitol can be increased when it is combined with Lapatinib.Approved, Investigational
Mefenamic acidThe metabolism of Mefenamic acid can be decreased when combined with Lapatinib.Approved
MeloxicamThe metabolism of Meloxicam can be decreased when combined with Lapatinib.Approved, Vet Approved
MephenytoinThe metabolism of Mephenytoin can be decreased when combined with Lapatinib.Investigational, Withdrawn
MethadoneLapatinib may increase the QTc-prolonging activities of Methadone.Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Lapatinib.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Lapatinib.Approved, Vet Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Lapatinib.Approved, Investigational
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Lapatinib.Approved, Illicit
MifepristoneThe serum concentration of Lapatinib can be increased when it is combined with Mifepristone.Approved, Investigational
MirabegronThe serum concentration of Mirabegron can be increased when it is combined with Lapatinib.Approved
MirtazapineThe metabolism of Mirtazapine can be decreased when combined with Lapatinib.Approved
MitotaneThe serum concentration of Lapatinib can be decreased when it is combined with Mitotane.Approved
MitoxantroneThe serum concentration of Mitoxantrone can be increased when it is combined with Lapatinib.Approved, Investigational
MoclobemideThe metabolism of Lapatinib can be decreased when combined with Moclobemide.Approved
ModafinilThe serum concentration of Lapatinib can be decreased when it is combined with Modafinil.Approved, Investigational
MorphineThe serum concentration of Morphine can be increased when it is combined with Lapatinib.Approved, Investigational
MoxifloxacinLapatinib may increase the QTc-prolonging activities of Moxifloxacin.Approved, Investigational
muraglitazarThe metabolism of muraglitazar can be decreased when combined with Lapatinib.Investigational
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Lapatinib.Approved, Investigational
NadololThe serum concentration of Nadolol can be increased when it is combined with Lapatinib.Approved
NafcillinThe serum concentration of Lapatinib can be decreased when it is combined with Nafcillin.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Lapatinib.Approved
NaloxoneThe serum concentration of Naloxone can be increased when it is combined with Lapatinib.Approved, Vet Approved
NaproxenThe metabolism of Naproxen can be decreased when combined with Lapatinib.Approved, Vet Approved
NefazodoneThe serum concentration of Lapatinib can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Lapatinib can be increased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Lapatinib can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Lapatinib can be decreased when it is combined with Nevirapine.Approved
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Lapatinib.Approved
NicotineThe metabolism of Nicotine can be decreased when combined with Lapatinib.Approved
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Lapatinib.Approved
NilotinibLapatinib may increase the QTc-prolonging activities of Nilotinib.Approved, Investigational
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Lapatinib.Approved
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Lapatinib.Approved
NizatidineThe serum concentration of Nizatidine can be increased when it is combined with Lapatinib.Approved
OfloxacinLapatinib may increase the QTc-prolonging activities of Ofloxacin.Approved
OlanzapineThe serum concentration of Olanzapine can be increased when it is combined with Lapatinib.Approved, Investigational
OlaparibThe metabolism of Lapatinib can be decreased when combined with Olaparib.Approved
OlodaterolThe metabolism of Olodaterol can be decreased when combined with Lapatinib.Approved
OmbitasvirThe serum concentration of Ombitasvir can be increased when it is combined with Lapatinib.Approved
OmeprazoleThe metabolism of Lapatinib can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OndansetronLapatinib may increase the QTc-prolonging activities of Ondansetron.Approved
OsimertinibThe serum concentration of Lapatinib can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Lapatinib.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Lapatinib.Approved, Vet Approved
PalbociclibThe serum concentration of Lapatinib can be increased when it is combined with Palbociclib.Approved
PaliperidoneLapatinib may increase the QTc-prolonging activities of Paliperidone.Approved
PanobinostatLapatinib may increase the QTc-prolonging activities of Panobinostat.Approved, Investigational
PantoprazoleThe metabolism of Lapatinib can be decreased when combined with Pantoprazole.Approved
ParamethadioneThe metabolism of Paramethadione can be decreased when combined with Lapatinib.Approved
PazopanibLapatinib may increase the QTc-prolonging activities of Pazopanib.Approved
PentamidineLapatinib may increase the QTc-prolonging activities of Pentamidine.Approved
PentobarbitalThe serum concentration of Lapatinib can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
PerflutrenLapatinib may increase the QTc-prolonging activities of Perflutren.Approved
PerphenazineThe metabolism of Perphenazine can be decreased when combined with Lapatinib.Approved
PhenobarbitalThe serum concentration of Lapatinib can be decreased when it is combined with Phenobarbital.Approved
PhenprocoumonThe metabolism of Phenprocoumon can be decreased when combined with Lapatinib.Approved
PhenytoinThe serum concentration of Lapatinib can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PimozideThe serum concentration of Pimozide can be increased when it is combined with Lapatinib.Approved
PioglitazoneThe metabolism of Lapatinib can be decreased when combined with Pioglitazone.Approved, Investigational
PiroxicamThe metabolism of Piroxicam can be decreased when combined with Lapatinib.Approved, Investigational
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Lapatinib.Approved
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Lapatinib.Approved
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Lapatinib.Approved
PosaconazoleThe serum concentration of Lapatinib can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Lapatinib.Approved
PrazosinThe serum concentration of Prazosin can be increased when it is combined with Lapatinib.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Lapatinib.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Lapatinib.Approved, Vet Approved
PrimaquineLapatinib may increase the QTc-prolonging activities of Primaquine.Approved
PrimidoneThe serum concentration of Lapatinib can be decreased when it is combined with Primidone.Approved, Vet Approved
ProcainamideLapatinib may increase the QTc-prolonging activities of Procainamide.Approved
ProgesteroneThe serum concentration of Progesterone can be increased when it is combined with Lapatinib.Approved, Vet Approved
PromazineLapatinib may increase the QTc-prolonging activities of Promazine.Approved, Vet Approved
PropafenoneLapatinib may increase the QTc-prolonging activities of Propafenone.Approved
PropofolThe metabolism of Propofol can be decreased when combined with Lapatinib.Approved, Investigational, Vet Approved
PropranololThe serum concentration of Propranolol can be increased when it is combined with Lapatinib.Approved, Investigational
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Lapatinib.Approved
QuetiapineLapatinib may increase the QTc-prolonging activities of Quetiapine.Approved
QuinidineLapatinib may increase the QTc-prolonging activities of Quinidine.Approved
QuinineLapatinib may increase the QTc-prolonging activities of Quinine.Approved
RabeprazoleThe metabolism of Lapatinib can be decreased when combined with Rabeprazole.Approved, Investigational
RanitidineThe serum concentration of Ranitidine can be increased when it is combined with Lapatinib.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Lapatinib.Approved, Investigational
RepaglinideThe metabolism of Repaglinide can be decreased when combined with Lapatinib.Approved, Investigational
ReserpineThe serum concentration of Reserpine can be increased when it is combined with Lapatinib.Approved
RifabutinThe serum concentration of Lapatinib can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Lapatinib can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Lapatinib can be decreased when it is combined with Rifapentine.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Lapatinib.Approved, Investigational
RiociguatThe metabolism of Riociguat can be decreased when combined with Lapatinib.Approved
RisperidoneThe serum concentration of Risperidone can be increased when it is combined with Lapatinib.Approved, Investigational
RitonavirThe serum concentration of Lapatinib can be increased when it is combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Lapatinib.Approved
RofecoxibThe metabolism of Rofecoxib can be decreased when combined with Lapatinib.Investigational, Withdrawn
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Lapatinib.Approved, Investigational
RosiglitazoneThe metabolism of Lapatinib can be decreased when combined with Rosiglitazone.Approved, Investigational
Salicylic acidThe serum concentration of Salicylic acid can be increased when it is combined with Lapatinib.Approved, Vet Approved
SaquinavirThe serum concentration of Lapatinib can be increased when it is combined with Saquinavir.Approved, Investigational
SecobarbitalThe metabolism of Lapatinib can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineThe metabolism of Selegiline can be decreased when combined with Lapatinib.Approved, Investigational, Vet Approved
SelexipagThe serum concentration of Selexipag can be increased when it is combined with Lapatinib.Approved
SeratrodastThe metabolism of Seratrodast can be decreased when combined with Lapatinib.Approved, Investigational
SertralineThe metabolism of Lapatinib can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Lapatinib can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Lapatinib.Approved
SiltuximabThe serum concentration of Lapatinib can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Lapatinib can be increased when it is combined with Simeprevir.Approved
SimvastatinThe metabolism of Simvastatin can be decreased when combined with Lapatinib.Approved
SitagliptinThe serum concentration of Sitagliptin can be increased when it is combined with Lapatinib.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be increased when it is combined with Lapatinib.Approved
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Lapatinib.Approved, Investigational
SotalolLapatinib may increase the QTc-prolonging activities of Sotalol.Approved
SparfloxacinThe serum concentration of Sparfloxacin can be increased when it is combined with Lapatinib.Approved
SphingosineThe serum concentration of Sphingosine can be increased when it is combined with Lapatinib.Experimental
St. John's WortThe serum concentration of Lapatinib can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Lapatinib can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Sulfadiazine can be decreased when combined with Lapatinib.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Lapatinib can be decreased when combined with Sulfamethoxazole.Approved
SulfinpyrazoneThe metabolism of Sulfinpyrazone can be decreased when combined with Lapatinib.Approved
SulfisoxazoleLapatinib may increase the QTc-prolonging activities of Sulfisoxazole.Approved, Vet Approved
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Lapatinib.Approved, Investigational
TamoxifenThe serum concentration of Tamoxifen can be increased when it is combined with Lapatinib.Approved
Taurocholic AcidThe serum concentration of Taurocholic Acid can be increased when it is combined with Lapatinib.Experimental
TazaroteneThe metabolism of Tazarotene can be decreased when combined with Lapatinib.Approved, Investigational
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Lapatinib.Approved
TelaprevirThe serum concentration of Lapatinib can be increased when it is combined with Telaprevir.Approved
TelavancinLapatinib may increase the QTc-prolonging activities of Telavancin.Approved
TelithromycinThe serum concentration of Lapatinib can be increased when it is combined with Telithromycin.Approved
TemazepamThe metabolism of Temazepam can be decreased when combined with Lapatinib.Approved
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Lapatinib.Approved
TerbinafineThe metabolism of Terbinafine can be decreased when combined with Lapatinib.Approved, Investigational, Vet Approved
TeriflunomideThe metabolism of Lapatinib can be decreased when combined with Teriflunomide.Approved
TestosteroneThe metabolism of Testosterone can be decreased when combined with Lapatinib.Approved, Investigational
TetrabenazineLapatinib may increase the QTc-prolonging activities of Tetrabenazine.Approved
TheophyllineThe metabolism of Theophylline can be decreased when combined with Lapatinib.Approved
ThioridazineLapatinib may increase the QTc-prolonging activities of Thioridazine.Approved
TicagrelorThe serum concentration of Ticagrelor can be increased when it is combined with Lapatinib.Approved
TiclopidineThe metabolism of Lapatinib can be decreased when combined with Ticlopidine.Approved
TimololThe serum concentration of Timolol can be increased when it is combined with Lapatinib.Approved
TocilizumabThe serum concentration of Lapatinib can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Tolbutamide can be decreased when combined with Lapatinib.Approved
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Lapatinib.Approved
TopiramateThe metabolism of Lapatinib can be decreased when combined with Topiramate.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Lapatinib.Approved, Investigational
TorasemideThe metabolism of Torasemide can be decreased when combined with Lapatinib.Approved
ToremifeneLapatinib may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
TranylcypromineThe metabolism of Lapatinib can be decreased when combined with Tranylcypromine.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Lapatinib.Approved, Investigational
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be increased when it is combined with Lapatinib.Approved
TretinoinThe metabolism of Tretinoin can be decreased when combined with Lapatinib.Approved, Investigational, Nutraceutical
TrimethadioneThe metabolism of Trimethadione can be decreased when combined with Lapatinib.Approved
TrimethoprimThe metabolism of Lapatinib can be decreased when combined with Trimethoprim.Approved, Vet Approved
TroglitazoneThe metabolism of Troglitazone can be decreased when combined with Lapatinib.Withdrawn
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Lapatinib.Approved
UmeclidiniumThe serum concentration of Umeclidinium can be increased when it is combined with Lapatinib.Approved
VandetanibLapatinib may increase the QTc-prolonging activities of Vandetanib.Approved
VecuroniumThe serum concentration of Vecuronium can be increased when it is combined with Lapatinib.Approved
VemurafenibLapatinib may increase the QTc-prolonging activities of Vemurafenib.Approved
VenetoclaxThe serum concentration of Venetoclax can be increased when it is combined with Lapatinib.Approved
VenlafaxineThe metabolism of Lapatinib can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Lapatinib can be decreased when combined with Verapamil.Approved
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Lapatinib.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Lapatinib.Approved, Investigational
VismodegibThe serum concentration of Vismodegib can be increased when it is combined with Lapatinib.Approved
VoriconazoleThe serum concentration of Lapatinib can be increased when it is combined with Voriconazole.Approved, Investigational
VortioxetineThe metabolism of Vortioxetine can be decreased when combined with Lapatinib.Approved
WarfarinThe metabolism of Warfarin can be decreased when combined with Lapatinib.Approved
ZafirlukastThe metabolism of Zafirlukast can be decreased when combined with Lapatinib.Approved, Investigational
ZidovudineThe serum concentration of Zidovudine can be increased when it is combined with Lapatinib.Approved
ZiprasidoneLapatinib may increase the QTc-prolonging activities of Ziprasidone.Approved
ZopicloneThe metabolism of Zopiclone can be decreased when combined with Lapatinib.Approved
ZuclopenthixolLapatinib may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
Food InteractionsNot Available
References
Synthesis Reference

DrugSyn.org

US6727256
General References
  1. 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. [PubMed:16418322 ]
  2. 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. [PubMed:15163842 ]
  3. 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. [PubMed:15955900 ]
  4. 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. [PubMed:17192538 ]
  5. Johnston SR, Leary A: Lapatinib: a novel EGFR/HER2 tyrosine kinase inhibitor for cancer. Drugs Today (Barc). 2006 Jul;42(7):441-53. [PubMed:16894399 ]
  6. 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. [PubMed:20110044 ]
  7. 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. [PubMed:18803986 ]
External Links
ATC CodesL01XE07
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.6201
Caco-2 permeable-0.5858
P-glycoprotein substrateSubstrate0.7403
P-glycoprotein inhibitor IInhibitor0.5414
P-glycoprotein inhibitor IINon-inhibitor0.7799
Renal organic cation transporterNon-inhibitor0.7442
CYP450 2C9 substrateNon-substrate0.6688
CYP450 2D6 substrateNon-substrate0.7644
CYP450 3A4 substrateSubstrate0.6619
CYP450 1A2 substrateInhibitor0.5386
CYP450 2C9 inhibitorNon-inhibitor0.5544
CYP450 2D6 inhibitorNon-inhibitor0.7861
CYP450 2C19 inhibitorInhibitor0.5274
CYP450 3A4 inhibitorInhibitor0.8065
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9104
Ames testNon AMES toxic0.543
CarcinogenicityNon-carcinogens0.6788
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5867 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.537
hERG inhibition (predictor II)Inhibitor0.8417
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
TabletOral250 mg/1
TabletOral250 mg
Tablet, film coatedOral250 mg
Prices
Unit descriptionCostUnit
Tykerb 250 mg tablet28.4USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2317589 No2007-08-082019-01-08Canada
CA2413134 No2010-05-112021-06-28Canada
US6391874 No1997-07-112017-07-11Us
US6713485 No2000-09-292020-09-29Us
US6727256 No1999-01-082019-01-08Us
US6828320 No1997-07-112017-07-11Us
US7157466 No2001-11-192021-11-19Us
US8513262 No1999-01-082019-01-08Us
US8821927 No2009-09-182029-09-18Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP5.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0223 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity152.42 m3·mol-1ChemAxon
Polarizability61.19 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound 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
ClassNaphthyridines
Sub ClassQuinazolines
Direct ParentQuinazolinamines
Alternative Parents
Substituents
  • Quinazolinamine
  • 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
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Ubiquitin protein ligase binding
Specific Function:
Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses. Known ligands include EGF, TGFA/TGF-alpha, amphiregulin, epigen/EPGN, BTC/betacellulin, epiregulin/EREG and HBEGF/heparin-binding EGF. Ligand binding triggers receptor homo- and/or heterodimerization and autophosphorylation on ke...
Gene Name:
EGFR
Uniprot ID:
P00533
Molecular Weight:
134276.185 Da
References
  1. Xia W, Mullin RJ, Keith BR, Liu LH, Ma H, Rusnak DW, Owens G, Alligood KJ, Spector NL: Anti-tumor activity of GW572016: a dual tyrosine kinase inhibitor blocks EGF activation of EGFR/erbB2 and downstream Erk1/2 and AKT pathways. Oncogene. 2002 Sep 12;21(41):6255-63. [PubMed:12214266 ]
  2. Grana TM, Sartor CI, Cox AD: Epidermal growth factor receptor autocrine signaling in RIE-1 cells transformed by the Ras oncogene enhances radiation resistance. Cancer Res. 2003 Nov 15;63(22):7807-14. [PubMed:14633707 ]
  3. Xia W, Liu LH, Ho P, Spector NL: Truncated ErbB2 receptor (p95ErbB2) is regulated by heregulin through heterodimer formation with ErbB3 yet remains sensitive to the dual EGFR/ErbB2 kinase inhibitor GW572016. Oncogene. 2004 Jan 22;23(3):646-53. [PubMed:14737100 ]
  4. Zhou H, Kim YS, Peletier A, McCall W, Earp HS, Sartor CI: Effects of the EGFR/HER2 kinase inhibitor GW572016 on EGFR- and HER2-overexpressing breast cancer cell line proliferation, radiosensitization, and resistance. Int J Radiat Oncol Biol Phys. 2004 Feb 1;58(2):344-52. [PubMed:14751502 ]
  5. Langer CJ: Emerging role of epidermal growth factor receptor inhibition in therapy for advanced malignancy: focus on NSCLC. Int J Radiat Oncol Biol Phys. 2004 Mar 1;58(3):991-1002. [PubMed:14967461 ]
  6. 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. [PubMed:15163842 ]
  7. Wood ER, Truesdale AT, McDonald OB, Yuan D, Hassell A, Dickerson SH, Ellis B, Pennisi C, Horne E, Lackey K, Alligood KJ, Rusnak DW, Gilmer TM, Shewchuk L: A unique structure for epidermal growth factor receptor bound to GW572016 (Lapatinib): relationships among protein conformation, inhibitor off-rate, and receptor activity in tumor cells. Cancer Res. 2004 Sep 15;64(18):6652-9. [PubMed:15374980 ]
  8. Vazquez-Martin A, Oliveras-Ferraros C, Cufi S, Del Barco S, Martin-Castillo B, Menendez JA: Lapatinib, a dual HER1/HER2 tyrosine kinase inhibitor, augments basal cleavage of HER2 extracellular domain (ECD) to inhibit HER2-driven cancer cell growth. J Cell Physiol. 2011 Jan;226(1):52-7. doi: 10.1002/jcp.22333. [PubMed:20658522 ]
  9. Johnston SR, Leary A: Lapatinib: a novel EGFR/HER2 tyrosine kinase inhibitor for cancer. Drugs Today (Barc). 2006 Jul;42(7):441-53. [PubMed:16894399 ]
  10. 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. [PubMed:20110044 ]
  11. 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. [PubMed:18803986 ]
  12. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Transmembrane signaling receptor activity
Specific Function:
Protein tyrosine kinase that is part of several cell surface receptor complexes, but that apparently needs a coreceptor for ligand binding. Essential component of a neuregulin-receptor complex, although neuregulins do not interact with it alone. GP30 is a potential ligand for this receptor. Regulates outgrowth and stabilization of peripheral microtubules (MTs). Upon ERBB2 activation, the MEMO1-...
Gene Name:
ERBB2
Uniprot ID:
P04626
Molecular Weight:
137909.27 Da
References
  1. Xia W, Liu LH, Ho P, Spector NL: Truncated ErbB2 receptor (p95ErbB2) is regulated by heregulin through heterodimer formation with ErbB3 yet remains sensitive to the dual EGFR/ErbB2 kinase inhibitor GW572016. Oncogene. 2004 Jan 22;23(3):646-53. [PubMed:14737100 ]
  2. Zhou H, Kim YS, Peletier A, McCall W, Earp HS, Sartor CI: Effects of the EGFR/HER2 kinase inhibitor GW572016 on EGFR- and HER2-overexpressing breast cancer cell line proliferation, radiosensitization, and resistance. Int J Radiat Oncol Biol Phys. 2004 Feb 1;58(2):344-52. [PubMed:14751502 ]
  3. Langer CJ: Emerging role of epidermal growth factor receptor inhibition in therapy for advanced malignancy: focus on NSCLC. Int J Radiat Oncol Biol Phys. 2004 Mar 1;58(3):991-1002. [PubMed:14967461 ]
  4. 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. [PubMed:15163842 ]
  5. Wood ER, Truesdale AT, McDonald OB, Yuan D, Hassell A, Dickerson SH, Ellis B, Pennisi C, Horne E, Lackey K, Alligood KJ, Rusnak DW, Gilmer TM, Shewchuk L: A unique structure for epidermal growth factor receptor bound to GW572016 (Lapatinib): relationships among protein conformation, inhibitor off-rate, and receptor activity in tumor cells. Cancer Res. 2004 Sep 15;64(18):6652-9. [PubMed:15374980 ]
  6. Grana TM, Sartor CI, Cox AD: Epidermal growth factor receptor autocrine signaling in RIE-1 cells transformed by the Ras oncogene enhances radiation resistance. Cancer Res. 2003 Nov 15;63(22):7807-14. [PubMed:14633707 ]
  7. Xia W, Mullin RJ, Keith BR, Liu LH, Ma H, Rusnak DW, Owens G, Alligood KJ, Spector NL: Anti-tumor activity of GW572016: a dual tyrosine kinase inhibitor blocks EGF activation of EGFR/erbB2 and downstream Erk1/2 and AKT pathways. Oncogene. 2002 Sep 12;21(41):6255-63. [PubMed:12214266 ]
  8. Vazquez-Martin A, Oliveras-Ferraros C, Cufi S, Del Barco S, Martin-Castillo B, Menendez JA: Lapatinib, a dual HER1/HER2 tyrosine kinase inhibitor, augments basal cleavage of HER2 extracellular domain (ECD) to inhibit HER2-driven cancer cell growth. J Cell Physiol. 2011 Jan;226(1):52-7. doi: 10.1002/jcp.22333. [PubMed:20658522 ]
  9. Johnston SR, Leary A: Lapatinib: a novel EGFR/HER2 tyrosine kinase inhibitor for cancer. Drugs Today (Barc). 2006 Jul;42(7):441-53. [PubMed:16894399 ]
  10. 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. [PubMed:20110044 ]
  11. 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. [PubMed:18803986 ]
  12. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. 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. [PubMed:18803986 ]
  2. van Erp NP, Gelderblom H, Guchelaar HJ: Clinical pharmacokinetics of tyrosine kinase inhibitors. Cancer Treat Rev. 2009 Dec;35(8):692-706. doi: 10.1016/j.ctrv.2009.08.004. Epub 2009 Sep 5. [PubMed:19733976 ]
  3. Teng WC, Oh JW, New LS, Wahlin MD, Nelson SD, Ho HK, Chan EC: Mechanism-based inactivation of cytochrome P450 3A4 by lapatinib. Mol Pharmacol. 2010 Oct;78(4):693-703. doi: 10.1124/mol.110.065839. Epub 2010 Jul 12. [PubMed:20624855 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. 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. [PubMed:18803986 ]
  2. van Erp NP, Gelderblom H, Guchelaar HJ: Clinical pharmacokinetics of tyrosine kinase inhibitors. Cancer Treat Rev. 2009 Dec;35(8):692-706. doi: 10.1016/j.ctrv.2009.08.004. Epub 2009 Sep 5. [PubMed:19733976 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. 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. [PubMed:18803986 ]
  2. van Erp NP, Gelderblom H, Guchelaar HJ: Clinical pharmacokinetics of tyrosine kinase inhibitors. Cancer Treat Rev. 2009 Dec;35(8):692-706. doi: 10.1016/j.ctrv.2009.08.004. Epub 2009 Sep 5. [PubMed:19733976 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. 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. [PubMed:18803986 ]
  2. van Erp NP, Gelderblom H, Guchelaar HJ: Clinical pharmacokinetics of tyrosine kinase inhibitors. Cancer Treat Rev. 2009 Dec;35(8):692-706. doi: 10.1016/j.ctrv.2009.08.004. Epub 2009 Sep 5. [PubMed:19733976 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Dai CL, Tiwari AK, Wu CP, Su XD, Wang SR, Liu DG, Ashby CR Jr, Huang Y, Robey RW, Liang YJ, Chen LM, Shi CJ, Ambudkar SV, Chen ZS, Fu LW: Lapatinib (Tykerb, GW572016) reverses multidrug resistance in cancer cells by inhibiting the activity of ATP-binding cassette subfamily B member 1 and G member 2. Cancer Res. 2008 Oct 1;68(19):7905-14. doi: 10.1158/0008-5472.CAN-08-0499. [PubMed:18829547 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Tap2 binding
Specific Function:
Involved in the transport of antigens from the cytoplasm to the endoplasmic reticulum for association with MHC class I molecules. Also acts as a molecular scaffold for the final stage of MHC class I folding, namely the binding of peptide. Nascent MHC class I molecules associate with TAP via tapasin. Inhibited by the covalent attachment of herpes simplex virus ICP47 protein, which blocks the pep...
Gene Name:
TAP1
Uniprot ID:
Q03518
Molecular Weight:
87216.855 Da
References
  1. Dai CL, Tiwari AK, Wu CP, Su XD, Wang SR, Liu DG, Ashby CR Jr, Huang Y, Robey RW, Liang YJ, Chen LM, Shi CJ, Ambudkar SV, Chen ZS, Fu LW: Lapatinib (Tykerb, GW572016) reverses multidrug resistance in cancer cells by inhibiting the activity of ATP-binding cassette subfamily B member 1 and G member 2. Cancer Res. 2008 Oct 1;68(19):7905-14. doi: 10.1158/0008-5472.CAN-08-0499. [PubMed:18829547 ]
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Drug created on May 16, 2007 11:27 / Updated on December 07, 2016 02:37