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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL554
CHEMBL554
Compound Name LAPATINIB
ChEMBL Synonyms GW-572016 | GW-2016 | Lapatinib | TYKERB | Lapatinib ditosylate monohydrate | LAPATINIB DITOSYLATE | LAPATINIB | GW572016F
Max Phase 4 (Approved)
Trade Names TYKERB
Molecular Formula C29H26ClFN4O4S

Additional synonyms for CHEMBL554 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CS(=O)(=O)CCNCc1oc(cc1)c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl) ...
Download SMILES
Standard InChI InChI=1S/C29H26ClFN4O4S/c1-40(36,37)12-11-32-16-23-7-10-27(3 ...
Download InChI
Standard InChI Key BCFGMOOMADDAQU-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Curated Drug Metabolism Pathways
  • HeCaToS Compounds
  • Orange Book
  • PubChem BioAssays
  • Sanger Institute Genomics of Drug Sensitivity in Cancer
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL554

Molecule Features

CHEMBL554 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Epidermal growth factor receptor erbB1 inhibitor Epidermal growth factor receptor erbB1 DailyMed
Receptor protein-tyrosine kinase erbB-2 inhibitor Receptor protein-tyrosine kinase erbB-2 DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
MELANOMAD008545EFO:0000756MELANOMA2ClinicalTrials
RENAL INSUFFICIENCY, CHRONICD051436EFO:0003884CHRONIC KIDNEY DISEASE1ClinicalTrials
BREAST NEOPLASMS, MALED018567EFO:0006861MALE BREAST CARCINOMA2ClinicalTrials
BREAST NEOPLASMSD001943EFO:0000305BREAST CARCINOMA4ClinicalTrials
DailyMed
ClinicalTrials
CARCINOMA, SQUAMOUS CELLD002294EFO:0000181HEAD AND NECK SQUAMOUS CELL CARCINOMA2ClinicalTrials
PROSTATIC NEOPLASMSD011471EFO:0001663PROSTATE CARCINOMA2ClinicalTrials
STOMACH NEOPLASMSD013274EFO:0000178GASTRIC CARCINOMA2ClinicalTrials
ESOPHAGEAL NEOPLASMSD004938EFO:0002916ESOPHAGEAL CARCINOMA2ClinicalTrials
NEOPLASMSD009369EFO:0000616NEOPLASM4ATC
CARCINOMA, SQUAMOUS CELLD002294EFO:0000707SQUAMOUS CELL CARCINOMA2ClinicalTrials
URINARY BLADDER NEOPLASMSD001749EFO:0000292BLADDER CARCINOMA2ClinicalTrials
ClinicalTrials
BREAST NEOPLASMSD001943EFO:0003869BREAST NEOPLASM4ClinicalTrials
ClinicalTrials
CARCINOMA, NON-SMALL-CELL LUNGD002289EFO:0003060NON-SMALL CELL LUNG CARCINOMA2ClinicalTrials
NEOPLASMSD009369EFO:0000311CANCER4ClinicalTrials

Clinical Data

ClinicalTrials.gov LAPATINIB
The Cochrane Collaboration LAPATINIB

Metabolites for CHEMBL554

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL554. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1824 Receptor protein-tyrosine kinase erbB-2 Homo sapiens 1.000
CHEMBL203 Epidermal growth factor receptor erbB1 Homo sapiens 1.000
CHEMBL3009 Receptor protein-tyrosine kinase erbB-4 Homo sapiens 1.000
CHEMBL4203 Dual specificity protein kinase CLK4 Homo sapiens 1.000
CHEMBL3356 Cytochrome P450 1A2 Homo sapiens 0.998
CHEMBL4224 Dual specificty protein kinase CLK1 Homo sapiens 0.993
CHEMBL2292 Dual-specificity tyrosine-phosphorylation regulated kinase 1A Homo sapiens 0.985
CHEMBL4225 Dual specificity protein kinase CLK2 Homo sapiens 0.705
CHEMBL3397 Cytochrome P450 2C9 Homo sapiens 0.486
CHEMBL5543 Dual specificity tyrosine-phosphorylation-regulated kinase 1B Homo sapiens 0.446



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1824 Receptor protein-tyrosine kinase erbB-2 Homo sapiens 1.000
CHEMBL203 Epidermal growth factor receptor erbB1 Homo sapiens 1.000
CHEMBL3009 Receptor protein-tyrosine kinase erbB-4 Homo sapiens 1.000
CHEMBL4203 Dual specificity protein kinase CLK4 Homo sapiens 1.000
CHEMBL4224 Dual specificty protein kinase CLK1 Homo sapiens 1.000
CHEMBL4225 Dual specificity protein kinase CLK2 Homo sapiens 1.000
CHEMBL5543 Dual specificity tyrosine-phosphorylation-regulated kinase 1B Homo sapiens 0.999
CHEMBL4948 Dual specificity mitogen-activated protein kinase kinase 5 Homo sapiens 0.998
CHEMBL2292 Dual-specificity tyrosine-phosphorylation regulated kinase 1A Homo sapiens 0.991
CHEMBL5014 Serine/threonine-protein kinase RIPK2 Homo sapiens 0.977
CHEMBL3981 Serine/threonine-protein kinase 10 Homo sapiens 0.906
CHEMBL1913 Platelet-derived growth factor receptor beta Homo sapiens 0.888
CHEMBL3356 Cytochrome P450 1A2 Homo sapiens 0.666
CHEMBL4202 Serine/threonine-protein kinase 2 Homo sapiens 0.446
CHEMBL4660 Lymphocyte differentiation antigen CD38 Homo sapiens 0.344
CHEMBL6166 Mitogen-activated protein kinase kinase kinase kinase 4 Homo sapiens 0.302

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
581.1 580.1347 6.04 11 114.72 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
7 2 2 8 2 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 6.34 6.3 6.26 5 40 0.18

Structural Alerts

There are 1 structural alerts for CHEMBL554. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01X - OTHER ANTINEOPLASTIC AGENTS
L01XE - Protein kinase inhibitors
L01XE07 - lapatinib

ChemSpider ChemSpider:BCFGMOOMADDAQU-UHFFFAOYSA-N
DailyMed lapatinib ditosylate
PubChem SID: 103905567 SID: 103905568 SID: 144206058 SID: 170465125 SID: 50100107
Wikipedia Lapatinib

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL554



ACToR 231277-92-2
Atlas lapatinib
BindingDB 5445
ChEBI 49603
DrugBank DB01259
DrugCentral 1548
eMolecules 6757269
EPA CompTox Dashboard DTXSID7046675
FDA SRS 0VUA21238F
Guide to Pharmacology 5692
Human Metabolome Database HMDB0015388
IBM Patent System 462D7D175FC760B785437626B712459C
LINCS LSM-1051
MolPort MolPort-006-069-221
Nikkaji J1.859.987B
PDBe FMM
PharmGKB PA152241907
PubChem 208908
PubChem: Thomson Pharma 14911387
Selleck lapatinib
SureChEMBL SCHEMBL8100
ZINC ZINC000001550477

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/BCFGMOOMADDAQU-UHFFFAOYSA-N spacer
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