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].
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: afatinib

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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-1220611, R-HSA-1225978, R-HSA-9652264, R-HSA-9665121, R-HSA-9665311, R-HSA-9665702, R-HSA-9665412
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
Search UniChem for chemical match using the InChIKey ULXXDDBFHOBEHA-CWDCEQMOSA-N
Search UniChem for chemicals with the same backbone ULXXDDBFHOBEHA
SynPHARM 79548 (in complex with epidermal growth factor receptor)
Wikipedia Afatinib