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Gefitinib information


Gefitinib
Clinical data
Pronunciation/ɡɛˈfɪtɪnɪb/
Trade namesIressa, others
Other namesZD1839
AHFS/Drugs.comMonograph
MedlinePlusa607002
License data
  • US DailyMed: Gefitinib
Pregnancy
category
  • AU: C
Routes of
administration
By mouth
ATC code
  • L01EB01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[1]
  • CA: ℞-only[2]
  • UK: POM (Prescription only)
  • US: ℞-only[3]
  • EU: Rx-only[4]
Pharmacokinetic data
Bioavailability59% (oral)
Protein binding90%
MetabolismLiver (mainly CYP3A4)
Elimination half-life6–49 hours
ExcretionFeces
Identifiers
IUPAC name
  • N-(3-chloro-4-fluoro-phenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine
CAS Number
  • 184475-35-2 checkY
PubChem CID
  • 123631
IUPHAR/BPS
  • 4941
DrugBank
  • DB00317 checkY
ChemSpider
  • 110217 checkY
UNII
  • S65743JHBS
KEGG
  • D01977 checkY
ChEBI
  • CHEBI:49668 checkY
ChEMBL
  • ChEMBL939 checkY
CompTox Dashboard (EPA)
  • DTXSID8041034 Edit this at Wikidata
ECHA InfoCard100.171.043 Edit this at Wikidata
Chemical and physical data
FormulaC22H24ClFN4O3
Molar mass446.91 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • C1COCCN1CCCOc2c(OC)cc3ncnc(c3c2)Nc4cc(Cl)c(F)cc4
InChI
  • 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) checkY
  • Key:XGALLCVXEZPNRQ-UHFFFAOYSA-N checkY
  (verify)

Gefitinib, sold under the brand name Iressa, is a medication used for certain breast, lung and other cancers. Gefitinib is an EGFR inhibitor, like erlotinib, which interrupts signaling through the epidermal growth factor receptor (EGFR) in target cells. Therefore, it is only effective in cancers with mutated and overactive EGFR, but resistances to gefitinib can arise through other mutations. It is marketed by AstraZeneca and Teva.

It is on the World Health Organization's List of Essential Medicines.[5] It is available as a generic medication.[6]

  1. ^ https://www.tga.gov.au/resources/auspar/auspar-gefitinib
  2. ^ "Iressa Product information". Health Canada. 17 December 2003. Retrieved 31 March 2024.
  3. ^ "Iressa- gefitinib tablet, coated". DailyMed. 28 February 2023. Retrieved 31 March 2024.
  4. ^ "Iressa EPAR". European Medicines Agency (EMA). 24 June 2009. Retrieved 31 March 2024.
  5. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  6. ^ "First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). 17 October 2022. Retrieved 28 November 2022.

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