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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL554
CHEMBL554
Compound Name LAPATINIB
ChEMBL Synonyms Lapatinib ditosylate monohydrate | GW-2016 | TYVERB | TYKERB | GW572016F | Lapatinib | GW-572016 | LAPATINIB DITOSYLATE
Max Phase 4 (Approved)
Trade Names TYKERB | TYVERB
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
  • Patent Bioactivity Data
  • 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
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma1ClinicalTrials
Stomach NeoplasmsD013274EFO:0000178gastric carcinoma2ClinicalTrials
ClinicalTrials
GliosarcomaD018316EFO:1001465gliosarcoma2ClinicalTrials
Endometrial NeoplasmsD016889EFO:1001512endometrial carcinoma2ClinicalTrials
Thyroid NeoplasmsD013964EFO:0002892thyroid carcinoma1ClinicalTrials
AdenocarcinomaD000230EFO:0000228adenocarcinoma2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma4ClinicalTrials
FDA
ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000181head and neck squamous cell carcinoma2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
ClinicalTrials
Breast NeoplasmsD001943EFO:0003869breast neoplasm4ClinicalTrials
ClinicalTrials
Colorectal NeoplasmsD015179EFO:0000365colorectal adenocarcinoma2ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma2ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme2ClinicalTrials
MelanomaD008545EFO:0000756melanoma2ClinicalTrials
NeuroblastomaD009447EFO:0000621neuroblastoma2ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma2ClinicalTrials
ClinicalTrials
Uterine NeoplasmsD014594EFO:0003859uterine neoplasm2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma1ClinicalTrials
Endometrial NeoplasmsD016889EFO:0004230endometrial neoplasm1ClinicalTrials
Pituitary NeoplasmsD010911EFO:1000478Pituitary Gland Adenoma2ClinicalTrials
Renal Insufficiency, ChronicD051436EFO:0003884chronic kidney disease1ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000292bladder carcinoma2ClinicalTrials
ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma2ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer2ClinicalTrials
ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials
ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001061cervical carcinoma2ClinicalTrials
Breast Neoplasms, MaleD018567EFO:0006861male breast carcinoma3ClinicalTrials
Stomach NeoplasmsD013274EFO:0000503gastric adenocarcinoma2ClinicalTrials
Brain DiseasesD001927EFO:0005774brain disease3ClinicalTrials
LymphomaD008223EFO:0000574lymphoma1ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000707squamous cell carcinoma2ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma2ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0006859head and neck malignant neoplasia1ClinicalTrials

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
CHEMBL203 Epidermal growth factor receptor erbB1 Homo sapiens 1.000
CHEMBL1824 Receptor protein-tyrosine kinase erbB-2 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 0.999
CHEMBL4224 Dual specificty protein kinase CLK1 Homo sapiens 0.766
CHEMBL3397 Cytochrome P450 2C9 Homo sapiens 0.753



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL203 Epidermal growth factor receptor erbB1 Homo sapiens 1.000
CHEMBL1824 Receptor protein-tyrosine kinase erbB-2 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
CHEMBL5014 Serine/threonine-protein kinase RIPK2 Homo sapiens 1.000
CHEMBL4224 Dual specificty protein kinase CLK1 Homo sapiens 1.000
CHEMBL4225 Dual specificity protein kinase CLK2 Homo sapiens 0.999
CHEMBL4948 Dual specificity mitogen-activated protein kinase kinase 5 Homo sapiens 0.999
CHEMBL4202 Serine/threonine-protein kinase 2 Homo sapiens 0.968
CHEMBL5543 Dual specificity tyrosine-phosphorylation-regulated kinase 1B Homo sapiens 0.963
CHEMBL1913 Platelet-derived growth factor receptor beta Homo sapiens 0.955
CHEMBL3981 Serine/threonine-protein kinase 10 Homo sapiens 0.928
CHEMBL3356 Cytochrome P450 1A2 Homo sapiens 0.802
CHEMBL4660 Lymphocyte differentiation antigen CD38 Homo sapiens 0.485
CHEMBL6166 Mitogen-activated protein kinase kinase kinase kinase 4 Homo sapiens 0.354

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
581.1 580.1347 6.14 11 106.35 NEUTRAL


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


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
ChemicalBook CB8855402
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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