afatinib   Click here for help

GtoPdb Ligand ID: 5667

Synonyms: BIBW2992 | Gilotrif®
Approved drug PDB Ligand
afatinib is an approved drug (EMA & FDA (2013))
Compound class: Synthetic organic
Comment: Afatinib is a second-generation, irreversible, covalently-bound EGFR tyrosine kinase inhibitor. It potently and selectively inhibits EGFR and Erbb2 [3,5,7]. Although afatinib demonstrates improved activity against the gatekeeper EGFR T790M resistance mutation, it is equally potent against the wild-type receptor, leading to dose-limiting toxicities and a narrow safety window [8]. Third generation, wild-type sparing inhibitors such as nazartinib are in development to circumvent this problem [4].
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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: afatinib

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 CDK toolkit. 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 7
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 88.61
Molecular weight 485.16
XLogP 3.1
No. Lipinski's rules broken 0
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.

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Canonical SMILES CN(CC=CC(=O)Nc1cc2c(ncnc2cc1OC1COCC1)Nc1ccc(c(c1)Cl)F)C
Isomeric SMILES CN(C/C=C/C(=O)Nc1cc2c(ncnc2cc1O[C@@H]1COCC1)Nc1ccc(c(c1)Cl)F)C
InChI InChI=1S/C24H25ClFN5O3/c1-31(2)8-3-4-23(32)30-21-11-17-20(12-22(21)34-16-7-9-33-13-16)27-14-28-24(17)29-15-5-6-19(26)18(25)10-15/h3-6,10-12,14,16H,7-9,13H2,1-2H3,(H,30,32)(H,27,28,29)/b4-3+/t16-/m0/s1
InChI Key ULXXDDBFHOBEHA-CWDCEQMOSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA & FDA (2013))
IUPAC Name Click here for help
(2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[(3S)-oxolan-3-yloxy]quinazolin-6-yl}-4-(dimethylamino)but-2-enamide
International Nonproprietary Names Click here for help
INN number INN
9230 afatinib
Synonyms Click here for help
BIBW2992 | Gilotrif®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-1220577
Reactome Reaction Reactome logo R-HSA-1225978, R-HSA-9652264, R-HSA-9665412, R-HSA-9665311, R-HSA-9665702, R-HSA-9665121, R-HSA-1220611
Other databases
CAS Registry No. 850140-72-6
ChEMBL Ligand CHEMBL1173655
DrugBank Ligand DB08916
DrugCentral Ligand 4318
GtoPdb PubChem SID 178102295
PubChem CID 10184653
RCSB PDB Ligand 0WM
Search Google for chemical match using the InChIKey ULXXDDBFHOBEHA-CWDCEQMOSA-N
Search Google for chemicals with the same backbone ULXXDDBFHOBEHA
Search PubMed clinical trials afatinib
Search PubMed titles afatinib
Search PubMed titles/abstracts afatinib
SynPHARM 79548 (in complex with epidermal growth factor receptor)
UniChem Compound Search for chemical match using the InChIKey ULXXDDBFHOBEHA-CWDCEQMOSA-N
UniChem Connectivity Search for chemical match using the InChIKey ULXXDDBFHOBEHA-CWDCEQMOSA-N
Wikipedia Afatinib