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gefitinib   Click here for help

GtoPdb Ligand ID: 4941

Synonyms: Iressa® | ZD 1839 | ZD1839
Approved drug PDB Ligand
gefitinib is an approved drug (FDA (2003), EMA (2009))
Compound class: Synthetic organic
Comment: Gefitinib is an orally active Type-1 kinase inhibitor and was first approved by the US FDA in 2003. Gefitinib has selectivity for the EGFR [6].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: gefitinib

gefitinib is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 68.74
Molecular weight 446.15
XLogP 3.18
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COc1cc2ncnc(c2cc1OCCCN1CCOCC1)Nc1ccc(c(c1)Cl)F
Isomeric SMILES COc1cc2ncnc(c2cc1OCCCN1CCOCC1)Nc1ccc(c(c1)Cl)F
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)
InChI Key XGALLCVXEZPNRQ-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (2003)  |  EU EMA (2009)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
N-(3-chloro-4-fluorophenyl)-7-methoxy-6-[3-(morpholin-4-yl)propoxy]quinazolin-4-amine
International Nonproprietary Names Click here for help
INN number INN
8204 gefitinib
Synonyms Click here for help
Iressa® | ZD 1839 | ZD1839
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-1169429
Reactome Reaction Reactome logo R-HSA-9665121, R-HSA-1220610
Other databases
CAS Registry No. 184475-35-2
ChEBI CHEBI:49668
ChEMBL Ligand CHEMBL939
DrugBank Ligand DB00317
DrugCentral Ligand 1282
GtoPdb PubChem SID 178101639
PubChem CID 123631
RCSB PDB Ligand IRE
Search Google for chemical match using the InChIKey XGALLCVXEZPNRQ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XGALLCVXEZPNRQ
Search PubMed clinical trials gefitinib
Search PubMed titles gefitinib
Search PubMed titles/abstracts gefitinib
SynPHARM 78743 (in complex with epidermal growth factor receptor)
81180 (in complex with epidermal growth factor receptor)
UniChem Compound Search for chemical match using the InChIKey XGALLCVXEZPNRQ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XGALLCVXEZPNRQ-UHFFFAOYSA-N
Wikipedia Gefitinib

Product suppliers

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Sponsored products disclaimer

Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

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MedChemExpress
Gefitinib (links to external site)
Cat. No. HY-50895
Gefitinib (Standard) (links to external site)
Cat. No. HY-50895R