IRE

Gefitinib

Created: 2006-05-25
Last modified:  2024-03-19

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Chemical Details

Formal Charge0
Atom Count55
Chiral Atom Count0
Bond Count58
Aromatic Bond Count17
2D diagram of IRE
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Chemical Component Summary

NameGefitinib
Systematic Name (OpenEye OEToolkits)~{N}-(3-chloranyl-4-fluoranyl-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine
FormulaC22 H24 Cl F N4 O3
Molecular Weight446.902
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01Fc1ccc(cc1Cl)Nc1ncnc2cc(OC)c(cc12)OCCCN1CCOCC1
SMILESCACTVS3.385COc1cc2ncnc(Nc3ccc(F)c(Cl)c3)c2cc1OCCCN4CCOCC4
SMILESOpenEye OEToolkits2.0.7COc1cc2c(cc1OCCCN3CCOCC3)c(ncn2)Nc4ccc(c(c4)Cl)F
Canonical SMILESCACTVS3.385 COc1cc2ncnc(Nc3ccc(F)c(Cl)c3)c2cc1OCCCN4CCOCC4
Canonical SMILESOpenEye OEToolkits2.0.7 COc1cc2c(cc1OCCCN3CCOCC3)c(ncn2)Nc4ccc(c(c4)Cl)F
InChIInChI1.06 InChI=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)
InChIKeyInChI1.06 XGALLCVXEZPNRQ-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00317 
NameGefitinib
Groups
  • approved
  • investigational
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.
Synonyms
  • N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-morpholinyl)propoxy)-4-quinazolinamine
  • 4-(3'-chloro-4'-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline
  • Gefitinib
Brand Names
  • Gefitinib
  • Jamp Gefitinib
  • Apo-gefitinib
  • Auro-gefitinib
  • Gefitinib Mylan
IndicationFor the continued treatment of patients with locally advanced or metastatic non-small cell lung cancer after failure of either platinum-based or docetaxel chemotherapies.
Categories
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • BCRP/ABCG2 Inhibitors
  • BCRP/ABCG2 Substrates
  • Cytochrome P-450 CYP2C19 Inhibitors
ATC-CodeL01EB01
CAS number184475-35-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Epidermal growth factor receptorMRPSGTAGAALLALLAALCPASRALEEKKVCQGTSNKLTQLGTFEDHFLS...unknownantagonist
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknownsubstrate
Cytochrome P450 1A1MLFPISMSATEFLLASVIFCLVFWVIRASRPQVPKGLKNPPGPWGWPLIG...unknownsubstrate,inhibitor
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknowninhibitor
Cytochrome P450 2C19MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL939
PubChem 123631
ChEMBL CHEMBL939
ChEBI CHEBI:49668
CCDC/CSD JUYTUU, FARRUM02, FARRUM03, FARRUM04, FARRUM01, IRIZAL, FARRUM, VUSJOL, NANBIR, PEDMUK, PEDGUE
COD 7217661, 7217662