Structure via PubChem · Public domain (PubChem)
gefitinib
Sign in to saveAlso known as ZD 1839, ZD1839, 4-(3′-chloro-4′-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline, N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(4-morpholinyl)propoxy]-4-quinazolinamine
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.
Chemical data
- Formula
- C22H24ClFN4O3
- Molecular weight
- 446.9 g/mol
- IUPAC name
- N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine
- SMILES
- COC1=C(C=C2C(=C1)N=CN=C2NC3=CC(=C(C=C3)F)Cl)OCCCN4CCOCC4
- InChIKey
- XGALLCVXEZPNRQ-UHFFFAOYSA-N
- XLogP
- 4.1
- Polar surface area
- 68.7 Ų
- H-bond donors
- 1
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Research
9,418 papers- Gefitinib.Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer · 2018
- Gefitinib.Profiles of drug substances, excipients, and related methodology · 2014
- Gefitinib Alone Versus Gefitinib Plus Chemotherapy for Non-Small-Cell Lung Cancer With Mutated Epidermal Growth Factor Receptor: NEJ009 Study.Journal of clinical oncology : official journal of the American Society of Clinical Oncology · 2020
- FGL1 regulates acquired resistance to Gefitinib by inhibiting apoptosis in non-small cell lung cancer.Respiratory research · 2020
- Gefitinib: An Updated Review of its Role in the Cancer Management, its Nanotechnological Interventions, Recent Patents and Clinical Trials.Recent patents on anti-cancer drug discovery · 2023
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 446.152
- Has use
- medication
Show 8 more facts
- chemical formula
- C₂₂H₂₄ClFN₄O₃
- found in taxon
- Streptomyces
- World Health Organisation international non-proprietary name
- gefitinib
- Commons category
- Gefitinib
- canonical SMILES
- COC1=C(C=C2C(=C1)N=CN=C2NC3=CC(=C(C=C3)F)Cl)OCCCN4CCOCC4
- subject has role
- tyrosine-kinase inhibitor
- physically interacts with
- epidermal growth factor receptor
- isomeric SMILES
- COc1cc2c(cc1OCCCN3CCOCC3)/C(=N/c4ccc(c(c4)Cl)F)/N=CN2
via Wikidata · CC0
~8 min read
Encyclopedic overview
9 sectionsContents
- Mechanism of action
- Clinical uses
- Experimental uses
- Studies
- EGFR diagnostic tests
- Adverse effects
- Resistance
- References
- External links
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.
Gefitinib is a therapeutic alternative on the World Health Organization's List of Essential Medicines. It is available as a generic medication.
Excerpted from Wikipedia’s “gefitinib” article, available under the CC BY-SA 4.0 licence.