Gefitinib (CHEM017631)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:30:16 UTC
Update Date2016-11-09 01:15:38 UTC
Accession NumberCHEM017631
Identification
Common NameGefitinib
ClassSmall Molecule
DescriptionGefitinib (originally coded ZD1839) is a drug used in the treatment of certain types of cancer. Acting in a similar manner to erlotinib (marketed as Tarceva), gefitinib selectively targets the mutant proteins in malignant cells. It is marketed by AstraZeneca under the trade name Iressa.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxr-9424700000-182dba69c82bee61cbe2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-1511900000-d0570bedf59699989575Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0193000000-38bb088cc8af6a0e12a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-1511900000-d0570bedf59699989575Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0201900000-dafa6866c6b59a71a89eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2904200000-011d82a75223a5017b87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-009l-9402000000-d87048e0478c6d231bfeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0004900000-bb4c9a2e360df1c7e52eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014s-3019400000-c4f741a0f46f6e8edd9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uy0-3279000000-593bcb0bda5ac3068617Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-f5b40d44879371ef81fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0005900000-a102859e7a71e3a4e883Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1029000000-4b9f808b7f687fe38a43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000900000-fc203d826511c11b8cd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fba-1901400000-c8c0d48bbd64a7e7fa9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9515200000-6abbaa993868c8b744f4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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