afatinib

Ligand id: 5667

Name: afatinib

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 88.61
Molecular weight 485.16
XLogP 3.06
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (source: EMA & FDA (2013))
IUPAC Name
(2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[(3S)-oxolan-3-yloxy]quinazolin-6-yl}-4-(dimethylamino)but-2-enamide
International Nonproprietary Names
INN number INN
9230 afatinib
Synonyms
BIBW2992
Gilotrif®
Database Links
CAS Registry No. 850140-72-6
ChEMBL Ligand CHEMBL1173655
DrugBank Ligand DB08916
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
Wikipedia Afatinib
Comments
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].