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Details

Stereochemistry ACHIRAL
Molecular Formula C29H26ClFN4O4S
Molecular Weight 581.058
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LAPATINIB

SMILES

CS(=O)(=O)CCNCC1=CC=C(O1)C2=CC=C3N=CN=C(NC4=CC=C(OCC5=CC=CC(F)=C5)C(Cl)=C4)C3=C2

InChI

InChIKey=BCFGMOOMADDAQU-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Molecular Formula C29H26ClFN4O4S
Molecular Weight 581.058
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

Unknown
123738
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:24:33 UTC 2023
Edited
by admin
on Fri Dec 15 16:24:33 UTC 2023
Record UNII
0VUA21238F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LAPATINIB
EMA EPAR   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
LAPATINIB [EMA EPAR]
Common Name English
lapatinib [INN]
Common Name English
GSK-572016
Code English
GW-572016X
Code English
LAPATINIB [MI]
Common Name English
GW572016
Code English
LAPATINIB [VANDF]
Common Name English
GW-572016
Code English
Lapatinib [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175605
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
NDF-RT N0000175076
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
WHO-VATC QL01XE07
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
NCI_THESAURUS C155764
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
LIVERTOX NBK547971
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
NCI_THESAURUS C2167
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
NCI_THESAURUS C129825
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
FDA ORPHAN DRUG 284209
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
WHO-ATC L01XE07
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
Code System Code Type Description
SMS_ID
100000089379
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL554
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
RXCUI
480167
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY RxNorm
LACTMED
Lapatinib
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
DRUG CENTRAL
1548
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
MESH
C490728
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
NSC
727989
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
PUBCHEM
208908
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
NCI_THESAURUS
C26653
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
DAILYMED
0VUA21238F
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
EVMPD
SUB25379
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
IUPHAR
5692
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
HSDB
8209
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID7046675
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
MERCK INDEX
m6688
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY Merck Index
INN
8378
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
WIKIPEDIA
LAPATINIB
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
CAS
231277-92-2
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
DRUG BANK
DB01259
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
FDA UNII
0VUA21238F
Created by admin on Fri Dec 15 16:24:33 UTC 2023 , Edited by admin on Fri Dec 15 16:24:33 UTC 2023
PRIMARY
Related Record Type Details
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
Lapatinib is a mechanism-based inactivator of CYP3A4, most likely via the formation and further oxidation of its O-dealkylated metabolite to a quinoneimine that covalently modifies the CYP3A4 apoprotein and/or heme moiety.
TIME-DEPENDENT INHIBITION
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
EPIDERMAL GROWTH FACTOR RECEPTOR
TARGET -> INHIBITOR
Structure of LAPATINIB DITOSYLATE
SALT/SOLVATE -> PARENT
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
Structure of LAPATINIB
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
Related Record Type Details
Structure of 2-FURANCARBOXYLIC ACID, 5-(4-((3-CHLORO-4-((3-FLUOROPHENYL)METHOXY)PHENYL)AMINO)-6-QUINAZOLINYL)-
METABOLITE -> PARENT
Structure of O-DEALKYLATED LAPATINIB
METABOLITE TOXIC -> PARENT
Specifically, the structure of O-dealkylated lapatinib has the potential to generate a reactive quinoneimine similar to the model hepatotoxin acetaminophen. lapatinib is a mechanism-based inactivator of CYP3A4, most likely via the formation and further oxidation of its O-dealkylated metabolite to a quinoneimine that covalently modifies the CYP3A4 apoprotein and/or heme moiety.
MAJOR
Structure of 4-QUINAZOLINAMINE, N-(3-CHLORO-4-((3-FLUOROPHENYL)METHOXY)PHENYL)-6-(5-(((2-(METHYLSULFONYL)ETHYL)OXIDOIMINO)METHYL)-2-FURANYL)-
METABOLITE -> PARENT
Structure of 2(1H)-QUINAZOLINONE, 4-((3-CHLORO-4-HYDROXYPHENYL)AMINO)-6-(5-(((2-(METHYLSULFONYL)ETHYL)AMINO)METHYL)-2-FURANYL)-
METABOLITE -> PARENT
Structure of 4-QUINAZOLINAMINE, N-(3-CHLORO-4-((3-FLUOROPHENYL)METHOXY)PHENYL)-6-(5-((HYDROXY(2-(METHYLSULFONYL)ETHYL)AMINO)METHYL)-2-FURANYL)-
METABOLITE -> PARENT
Structure of 6-(4-(3-CHLORO-4-((3-FLUOROPHENYL)METHOXY)ANILINO)QUINAZOLIN-6-YL)-1-(2-METHYLSULFONYLETHYL)PYRIDIN-1-IUM-3-OL
METABOLITE -> PARENT
Structure of (5-(4-(4-((3-FLUOROBENZYL)OXY)-3-CHLOROANILINO)-6-QUINAZOLINYL)-2-FURANCARBOXALDEHYDE
METABOLITE -> PARENT
Structure of N-DEALKYLATED LAPATINIB
METABOLITE -> PARENT
MAJOR
FECAL
Structure of 4-QUINAZOLINAMINE, N-(3-CHLORO-4-((3-FLUOROPHENYL)METHOXY)PHENYL)-6-(5-(((2-(METHYLSULFONYL)ETHYLIDENE)OXIDOAMINO)METHYL)-2-FURANYL)-
METABOLITE -> PARENT
Structure of N-DEALKYLATED LAPATINIB
METABOLITE -> PARENT
MAJOR
Related Record Type Details
Structure of LAPATINIB
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC
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