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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1173655
CHEMBL1173655
Compound Name AFATINIB
ChEMBL Synonyms BIBW-2992 | AFATINIB | AFATINIB DIMALEATE | BIBW2992 MA2 | BIBW2992
Max Phase 4 (Approved)
Trade Names
Molecular Formula C24H25ClFN5O3

Additional synonyms for CHEMBL1173655 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN(C)C\C=C\C(=O)Nc1cc2c(Nc3ccc(F)c(Cl)c3)ncnc2cc1O[C@H]4CCOC ...
Download SMILES
Standard InChI InChI=1S/C24H25ClFN5O3/c1-31(2)8-3-4-23(32)30-21-11-17-20(12 ...
Download InChI
Standard InChI Key ULXXDDBFHOBEHA-CWDCEQMOSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Manually Added Drugs
  • Orange Book
  • 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


CHEMBL1173655

Molecule Features

CHEMBL1173655 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N 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
Receptor protein-tyrosine kinase erbB-4 inhibitor Receptor protein-tyrosine kinase erbB-4 DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
CARCINOMA, SQUAMOUS CELLD002294EFO:0000707SQUAMOUS CELL CARCINOMA3ClinicalTrials
RHABDOMYOSARCOMAD012208EFO:0002918RHABDOMYOSARCOMA1ClinicalTrials
CARCINOMA, SQUAMOUS CELLD002294EFO:0000181HEAD AND NECK SQUAMOUS CELL CARCINOMA3ClinicalTrials
LUNG NEOPLASMSD008175EFO:0001071LUNG CARCINOMA2ClinicalTrials
PROSTATIC NEOPLASMSD011471EFO:0000673PROSTATE ADENOCARCINOMA2ClinicalTrials
RENAL INSUFFICIENCYD051437HP:0000083RENAL INSUFFICIENCY1ClinicalTrials
CARCINOMA, NON-SMALL-CELL LUNGD002289EFO:0003060NON-SMALL CELL LUNG CARCINOMA4DailyMed
ClinicalTrials
ClinicalTrials
HEAD AND NECK NEOPLASMSD006258EFO:0004284UPPER AERODIGESTIVE TRACT NEOPLASM3ClinicalTrials
GLIOMAD005910EFO:0000326CENTRAL NERVOUS SYSTEM CANCER2ClinicalTrials
LIVER DISEASESD008107EFO:0001421LIVER DISEASE1ClinicalTrials
NEOPLASMSD009369EFO:0000616NEOPLASM4ClinicalTrials
ATC
BREAST NEOPLASMSD001943EFO:0000305BREAST CARCINOMA2ClinicalTrials
BRAIN NEOPLASMSD001932EFO:0003833BRAIN NEOPLASM1ClinicalTrials
BREAST NEOPLASMSD001943EFO:0003869BREAST NEOPLASM2ClinicalTrials
GLIOBLASTOMAD005909EFO:0000519GLIOBLASTOMA MULTIFORME1ClinicalTrials
LYMPHOMAD008223EFO:0000574LYMPHOMA2ClinicalTrials

Clinical Data

ClinicalTrials.gov AFATINIB
The Cochrane Collaboration AFATINIB

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 CHEMBL1173655. 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
CHEMBL3009 Receptor protein-tyrosine kinase erbB-4 Homo sapiens 1.000
CHEMBL1824 Receptor protein-tyrosine kinase erbB-2 Homo sapiens 1.000
CHEMBL203 Epidermal growth factor receptor erbB1 Homo sapiens 1.000
CHEMBL4355 Serine/threonine-protein kinase GAK Homo sapiens 1.000
CHEMBL279 Vascular endothelial growth factor receptor 2 Homo sapiens 1.000
CHEMBL3981 Serine/threonine-protein kinase 10 Homo sapiens 1.000
CHEMBL3905 Tyrosine-protein kinase Lyn Homo sapiens 1.000
CHEMBL4937 Casein kinase I epsilon Homo sapiens 1.000
CHEMBL2250 Tyrosine-protein kinase BLK Homo sapiens 1.000
CHEMBL4948 Dual specificity mitogen-activated protein kinase kinase 5 Homo sapiens 1.000
CHEMBL258 Tyrosine-protein kinase LCK Homo sapiens 0.998
CHEMBL6191 SPS1/STE20-related protein kinase YSK4 Homo sapiens 0.997
CHEMBL3357 Interleukin-1 receptor-associated kinase 1 Homo sapiens 0.996
CHEMBL267 Tyrosine-protein kinase SRC Homo sapiens 0.986
CHEMBL4202 Serine/threonine-protein kinase 2 Homo sapiens 0.979
CHEMBL2041 Tyrosine-protein kinase receptor RET Homo sapiens 0.809
CHEMBL2007 Platelet-derived growth factor receptor alpha Homo sapiens 0.565
CHEMBL4224 Dual specificty protein kinase CLK1 Homo sapiens 0.562
CHEMBL4223 Tyrosine-protein kinase FRK Homo sapiens 0.520
CHEMBL2964 Dual specificity mitogen-activated protein kinase kinase 2 Homo sapiens 0.320



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
CHEMBL3981 Serine/threonine-protein kinase 10 Homo sapiens 1.000
CHEMBL4948 Dual specificity mitogen-activated protein kinase kinase 5 Homo sapiens 1.000
CHEMBL4937 Casein kinase I epsilon Homo sapiens 1.000
CHEMBL4367 Tyrosine-protein kinase TXK Homo sapiens 1.000
CHEMBL4355 Serine/threonine-protein kinase GAK Homo sapiens 1.000
CHEMBL5836 Ephrin type-B receptor 6 Homo sapiens 1.000
CHEMBL5579 Citron Rho-interacting kinase Homo sapiens 1.000
CHEMBL279 Vascular endothelial growth factor receptor 2 Homo sapiens 1.000
CHEMBL4526 Ephrin type-A receptor 6 Homo sapiens 1.000
CHEMBL3905 Tyrosine-protein kinase Lyn Homo sapiens 1.000
CHEMBL5014 Serine/threonine-protein kinase RIPK2 Homo sapiens 1.000
CHEMBL2634 Tyrosine-protein kinase CSK Homo sapiens 1.000
CHEMBL4718 MAP kinase-interacting serine/threonine-protein kinase MNK1 Homo sapiens 1.000
CHEMBL5699 Serine/threonine-protein kinase SIK2 Homo sapiens 1.000
CHEMBL2250 Tyrosine-protein kinase BLK Homo sapiens 1.000
CHEMBL4454 Tyrosine-protein kinase FGR Homo sapiens 1.000
CHEMBL258 Tyrosine-protein kinase LCK Homo sapiens 1.000

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
485.9 485.163 3.92 8 88.61 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
7 2 0 8 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
11.79 8.01 1.57 1.02 3 34 0.47

Structural Alerts

There are 4 structural alerts for CHEMBL1173655. 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
L01XE13 - afatinib

ChemSpider ChemSpider:ULXXDDBFHOBEHA-CWDCEQMOSA-N
DailyMed afatinib dimaleate
Wikipedia Afatinib

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1173655



ACToR 439081-18-2
BindingDB 50322823
ChEBI 61390
DrugBank DB08916
DrugCentral 4318
FDA SRS 41UD74L59M
Guide to Pharmacology 5667
LINCS LSM-43226
MolPort MolPort-009-679-394
Nikkaji J2.685.397D J3.363.130H
PDBe 0WM
PharmGKB PA165981154
PubChem 10184653
PubChem: Drugs of the Future 57304398
PubChem: Thomson Pharma 15180141
Selleck BIBW2992
SureChEMBL SCHEMBL185621
ZINC ZINC000003976838

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