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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2D Structure
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Physico-chemical Properties
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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
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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
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Molecular structure representations generated using Open Babel