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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL939
CHEMBL939
Compound Name GEFITINIB
ChEMBL Synonyms ZD1839 | GEFITINIB | IRESSA
Max Phase 4 (Approved)
Trade Names IRESSA
Molecular Formula C22H24ClFN4O3

Additional synonyms for CHEMBL939 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1cc2ncnc(Nc3ccc(F)c(Cl)c3)c2cc1OCCCN4CCOCC4
Standard InChI InChI=1S/C22H24ClFN4O3/c1-29-20-13-19-16(12-21(20)31-8-2-5-2 ...
Download InChI
Standard InChI Key XGALLCVXEZPNRQ-UHFFFAOYSA-N

Sources

  • BindingDB Database
  • British National Formulary
  • DrugMatrix
  • Open TG-GATEs
  • Orange Book
  • Patent Bioactivity Data
  • PubChem BioAssays
  • Sanger Institute Genomics of Drug Sensitivity in Cancer
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL939

Molecule Features

CHEMBL939 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule 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

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
GliosarcomaD018316EFO:1001465gliosarcoma2ClinicalTrials
MesotheliomaD008654EFO:0000588mesothelioma2ClinicalTrials
SarcomaD012509EFO:0000691sarcoma2ClinicalTrials
Skin NeoplasmsD012878EFO:0004198skin neoplasm2ClinicalTrials
Small Cell Lung CarcinomaD055752EFO:0000702small cell lung carcinoma2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma3ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000707squamous cell carcinoma3ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme2ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer2ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0004284upper aerodigestive tract neoplasm3ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials
Breast Neoplasms, MaleD018567EFO:0006861male breast carcinoma2ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma2ClinicalTrials
NeuroblastomaD009447EFO:0000621neuroblastoma2ClinicalTrials
Stomach NeoplasmsD013274EFO:0000178gastric carcinoma2ClinicalTrials
Breast NeoplasmsD001943EFO:0003869breast neoplasm3ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000181head and neck squamous cell carcinoma3ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma2ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000196metastatic prostate cancer2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0002890renal carcinoma2ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0006859head and neck malignant neoplasia3ClinicalTrials
Nasopharyngeal NeoplasmsD009303EFO:0004252nasopharyngeal neoplasm1ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
Urethral NeoplasmsD014523EFO:0003846urethral neoplasm2ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000708squamous cell lung carcinoma3ClinicalTrials
Neoplasms, Germ Cell and EmbryonalD009373EFO:0000514germ cell tumor2ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma1ClinicalTrials
Salivary Gland NeoplasmsD012468EFO:0003826salivary gland neoplasm2ClinicalTrials
Stomach NeoplasmsD013274EFO:0003897stomach neoplasm2ClinicalTrials
Uterine NeoplasmsD014594EFO:0003859uterine neoplasm2ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma2ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000292bladder carcinoma3ClinicalTrials

Clinical Data

ClinicalTrials.gov GEFITINIB
The Cochrane Collaboration GEFITINIB

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 CHEMBL939. 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
CHEMBL5147 Ephrin type-B receptor 4 Homo sapiens 1.000
CHEMBL2068 Ephrin type-A receptor 2 Homo sapiens 1.000
CHEMBL2041 Tyrosine-protein kinase receptor RET Homo sapiens 1.000
CHEMBL267 Tyrosine-protein kinase SRC Homo sapiens 1.000
CHEMBL1868 Vascular endothelial growth factor receptor 1 Homo sapiens 1.000
CHEMBL279 Vascular endothelial growth factor receptor 2 Homo sapiens 1.000
CHEMBL1913 Platelet-derived growth factor receptor beta Homo sapiens 1.000
CHEMBL4722 Serine/threonine-protein kinase Aurora-A Homo sapiens 1.000
CHEMBL4718 MAP kinase-interacting serine/threonine-protein kinase MNK1 Homo sapiens 1.000
CHEMBL4355 Serine/threonine-protein kinase GAK Homo sapiens 1.000
CHEMBL2185 Serine/threonine-protein kinase Aurora-B Homo sapiens 1.000
CHEMBL4202 Serine/threonine-protein kinase 2 Homo sapiens 1.000
CHEMBL3981 Serine/threonine-protein kinase 10 Homo sapiens 1.000
CHEMBL1955 Vascular endothelial growth factor receptor 3 Homo sapiens 1.000
CHEMBL4948 Dual specificity mitogen-activated protein kinase kinase 5 Homo sapiens 0.995
CHEMBL6191 SPS1/STE20-related protein kinase YSK4 Homo sapiens 0.990
CHEMBL2250 Tyrosine-protein kinase BLK Homo sapiens 0.981



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
CHEMBL5147 Ephrin type-B receptor 4 Homo sapiens 1.000
CHEMBL2068 Ephrin type-A receptor 2 Homo sapiens 1.000
CHEMBL279 Vascular endothelial growth factor receptor 2 Homo sapiens 1.000
CHEMBL2041 Tyrosine-protein kinase receptor RET Homo sapiens 1.000
CHEMBL1913 Platelet-derived growth factor receptor beta Homo sapiens 1.000
CHEMBL1868 Vascular endothelial growth factor receptor 1 Homo sapiens 1.000
CHEMBL267 Tyrosine-protein kinase SRC Homo sapiens 1.000
CHEMBL1955 Vascular endothelial growth factor receptor 3 Homo sapiens 1.000
CHEMBL3981 Serine/threonine-protein kinase 10 Homo sapiens 1.000
CHEMBL4722 Serine/threonine-protein kinase Aurora-A Homo sapiens 1.000
CHEMBL4202 Serine/threonine-protein kinase 2 Homo sapiens 1.000
CHEMBL4948 Dual specificity mitogen-activated protein kinase kinase 5 Homo sapiens 1.000
CHEMBL4355 Serine/threonine-protein kinase GAK Homo sapiens 1.000
CHEMBL2185 Serine/threonine-protein kinase Aurora-B Homo sapiens 1.000
CHEMBL4718 MAP kinase-interacting serine/threonine-protein kinase MNK1 Homo sapiens 1.000
CHEMBL5014 Serine/threonine-protein kinase RIPK2 Homo sapiens 1.000
CHEMBL5836 Ephrin type-B receptor 6 Homo sapiens 1.000

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
446.9 446.1521 4.28 8 68.74 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
7 1 0 7 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 7 2.7 2.56 3 31 0.52

Structural Alerts

There are 1 structural alerts for CHEMBL939. 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
L01XE02 - gefitinib

ChemSpider ChemSpider:XGALLCVXEZPNRQ-UHFFFAOYSA-N
DailyMed gefitinib
PubChem SID: 103905343 SID: 103905344 SID: 124892204 SID: 124892206 SID: 137275808 SID: 144205236 SID: 170464828 SID: 29215403 SID: 50100103
Wikipedia Gefitinib

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL939



ACToR 184475-35-2
Atlas gefitinib
BindingDB 5447
Brenda 21851 57709 17786
ChEBI 49668
ChemicalBook CB8120056
DrugBank DB00317
DrugCentral 1282
eMolecules 876432
EPA CompTox Dashboard DTXSID8041034
FDA SRS S65743JHBS
Guide to Pharmacology 4941
Human Metabolome Database HMDB0014462
IBM Patent System E570B600693D061902A57F63A8DC4571
LINCS LSM-1098
Mcule MCULE-6951584187
MolPort MolPort-000-883-335
Nikkaji J1.437.124I
PDBe IRE
PharmGKB PA131301952
PubChem 123631
PubChem: Drugs of the Future 12015033
PubChem: Thomson Pharma 14833109
Selleck Gefitinib
SureChEMBL SCHEMBL7866
ZINC ZINC000019632614

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