Gefitinib (CED0001399)

Record Information
Version1.0
Creation Date2016-05-22 04:30:16 UTC
Update Date2026-08-21 22:10:52 UTC
Accession NumberCHEM017631
Identification
Common NameGefitinib
ClassSmall Molecule
Description
Gefitinib is an organic compound with the formula C22H24ClFN4O3 and an average molecular weight of 446.90 g/mol. Gefitinib belongs to the benzodiazines, a subclass of diazanaphthalenes within the organic compounds. It functions as a biological inhibitor (PMC12533758) and a biological drug (PMC10559678). The compound acts as an antagonist of the epidermal growth factor receptor (EGFR). Gefitinib is utilized as a treatment for cancer (PMC9607420), specifically lung cancer (PMC4512945, PMC7170478), esophageal cancer (PMC12723240), and breast cancer (PMC7226512). It is noted to have a therapeutic effect on lung cancer (PMC12067445), although it is associated with rash (PMC13084601). The compound is found in or released from six recorded sources, including antineoplastic agents within healthcare, pharmaceuticals, and veterinary products. Other recorded sources include household cleaning and consumer products such as soap dispensers and non-electric simulated smoking devices, electrical and electronic equipment including television systems and electric hearing aids, and the preparation of malt in food, food processing, and cookware. The recorded exposure route for this compound is oral.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-(3'-Chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazolineChEBI
GefitinibumChEBI
IressaChEBI
IrressatChEBI
N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-4-quinazolinamineChEBI
ZD 1839ChEBI
ZD-1839ChEBI
ZD1839ChEBI
N-(3-Chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-4-quinazolinamideHMDB
Chemical FormulaC22H24ClFN4O3
Average Molecular Mass446.902 g/mol
Monoisotopic Mass446.152 g/mol
CAS Registry Number184475-35-2
IUPAC NameN-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(morpholin-4-yl)propoxy]quinazolin-4-amine
Traditional Namegefitinib
SMILESCOC1=C(OCCCN2CCOCC2)C=C2C(NC3=CC(Cl)=C(F)C=C3)=NC=NC2=C1
InChI IdentifierInChI=1S/C22H24ClFN4O3/c1-29-20-13-19-16(12-21(20)31-8-2-5-28-6-9-30-10-7-28)22(26-14-25-19)27-15-3-4-18(24)17(23)11-15/h3-4,11-14H,2,5-10H2,1H3,(H,25,26,27)
InChI KeyXGALLCVXEZPNRQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentQuinazolinamines
Alternative Parents
Substituents
  • Quinazolinamine
  • Anisole
  • Aniline or substituted anilines
  • Alkyl aryl ether
  • Aminopyrimidine
  • Chlorobenzene
  • Fluorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Morpholine
  • Oxazinane
  • Pyrimidine
  • Benzenoid
  • Imidolactam
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary amine
  • Azacycle
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Organofluoride
  • Organochloride
  • Organopnictogen compound
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.027 g/LALOGPS
logP4.02ALOGPS
logP3.75ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)16.11ChemAxon
pKa (Strongest Basic)6.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.74 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity117.51 m³·mol⁻¹ChemAxon
Polarizability46.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0uxr-9424700000-182dba69c82bee61cbe2Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-1511900000-d0570bedf59699989575Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0193000000-38bb088cc8af6a0e12a4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-1511900000-d0570bedf59699989575Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0201900000-dafa6866c6b59a71a89eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-2904200000-011d82a75223a5017b87Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-009l-9402000000-d87048e0478c6d231bfeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0004900000-bb4c9a2e360df1c7e52eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014s-3019400000-c4f741a0f46f6e8edd9fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uy0-3279000000-593bcb0bda5ac3068617Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0000900000-f5b40d44879371ef81fbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6t-0005900000-a102859e7a71e3a4e883Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1029000000-4b9f808b7f687fe38a43Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0000900000-fc203d826511c11b8cd1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fba-1901400000-c8c0d48bbd64a7e7fa9aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uk9-9515200000-6abbaa993868c8b744f4Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1068.0Log mg/kg[600:1900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
lung canceris_treatment_forNot AvailablePMC4512945 , PMC7170478
lung cancerhas_therapeutic_effect_onNot AvailablePMC12067445
canceris_treatment_forNot AvailablePMC9607420
breast canceris_treatment_forNot AvailablePMC7226512
rashassociated_withNot AvailablePMC13084601
esophageal canceris_treatment_forNot AvailablePMC12723240
Exposure Sources
Source IDSourceSectorReference
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
602MolluscicidesAgriculture & land managementNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Gefitinib Action Pathway
Gefitinib Action Pathway
Gefitinib Drug Metabolism Action Pathway
Gefitinib Drug Metabolism Action Pathway
Gefitinib Predicted Metabolism Pathway
Gefitinib Predicted Metabolism Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)1.55698
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)1.86838
Receptor tyrosine-protein kinase erbB-2 structureClick to view 3D structureReceptor tyrosine-protein kinase erbB-2P04626HumansPredicted (SEA)0.778492
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)3.03612
Aurora kinase A structureClick to view 3D structureAurora kinase AO14965HumansPredicted (SEA)1.86838
Platelet-derived growth factor receptor beta structureClick to view 3D structurePlatelet-derived growth factor receptor betaP09619HumansPredicted (SEA)0.934191
Aurora kinase B structureClick to view 3D structureAurora kinase BQ96GD4HumansPredicted (SEA)1.86838
Ephrin type-B receptor 4 structureClick to view 3D structureEphrin type-B receptor 4P54760HumansPredicted (SEA)0.544945
Receptor tyrosine-protein kinase erbB-4 structureClick to view 3D structureReceptor tyrosine-protein kinase erbB-4Q15303HumansPredicted (SEA)1.79053
Angiopoietin-1 receptor structureClick to view 3D structureAngiopoietin-1 receptorQ02763HumansPredicted (SEA)0.467095
Vascular endothelial growth factor receptor 3 structureClick to view 3D structureVascular endothelial growth factor receptor 3P35916HumansPredicted (SEA)1.63483
Mast/stem cell growth factor receptor Kit structureClick to view 3D structureMast/stem cell growth factor receptor KitP10721HumansPredicted (SEA)4.12601
Receptor tyrosine-protein kinase erbB-3 structureClick to view 3D structureReceptor tyrosine-protein kinase erbB-3P21860HumansPredicted (SEA)0.0778492
Proto-oncogene tyrosine-protein kinase receptor Ret structureClick to view 3D structureProto-oncogene tyrosine-protein kinase receptor RetP07949HumansPredicted (SEA)2.25763
Mitogen-activated protein kinase 14 structureClick to view 3D structureMitogen-activated protein kinase 14Q16539HumansPredicted (SEA)2.88042
Insulin-like growth factor 1 receptor structureClick to view 3D structureInsulin-like growth factor 1 receptorP08069HumansPredicted (SEA)4.28171
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)5.76084
Dual specificity mitogen-activated protein kinase kinase 1 structureClick to view 3D structureDual specificity mitogen-activated protein kinase kinase 1Q02750HumansPredicted (SEA)0.778492
Mitogen-activated protein kinase 8 structureClick to view 3D structureMitogen-activated protein kinase 8P45983HumansPredicted (SEA)2.80257
Tyrosine-protein kinase JAK3 structureClick to view 3D structureTyrosine-protein kinase JAK3P52333HumansPredicted (SEA)3.19182
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)3.03612
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)2.25763
Rho-associated protein kinase 2 structureClick to view 3D structureRho-associated protein kinase 2O75116HumansPredicted (SEA)2.41333
Serine/threonine-protein kinase Chk1 structureClick to view 3D structureSerine/threonine-protein kinase Chk1O14757HumansPredicted (SEA)2.02408
Serine/threonine-protein kinase Nek2 structureClick to view 3D structureSerine/threonine-protein kinase Nek2P51955HumansPredicted (SEA)1.79053
Concentrations
Not Available
External Links
DrugBank IDDB00317
HMDB IDHMDB0014462
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGefitinib
Chemspider ID110217
ChEBI ID49668
PubChem Compound ID123631
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sordella R, Bell DW, Haber DA, Settleman J: Gefitinib-sensitizing EGFR mutations in lung cancer activate anti-apoptotic pathways. Science. 2004 Aug 20;305(5687):1163-7. Epub 2004 Jul 29.
2. Pao W, Miller V, Zakowski M, Doherty J, Politi K, Sarkaria I, Singh B, Heelan R, Rusch V, Fulton L, Mardis E, Kupfer D, Wilson R, Kris M, Varmus H: EGF receptor gene mutations are common in lung cancers from "never smokers" and are associated with sensitivity of tumors to gefitinib and erlotinib. Proc Natl Acad Sci U S A. 2004 Sep 7;101(36):13306-11. Epub 2004 Aug 25.
3. FDA label
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=14981586
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15068398
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20573926
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20949670
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=27396387
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=28968167
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=29332330
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=29493460
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=29579334
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=29668619
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=30068310
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=30069771
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=30214852