nazartinib   Click here for help

GtoPdb Ligand ID: 9204

Synonyms: compound 47 [PMID: 27433829] | EGF-816 | EGF816
Compound class: Synthetic organic
Comment: EGF816 is an irreversible and selective inhibitor of EGFRs harbouring gatekeeper T790M, and sensitising L858R mutations, whilst sparing the wild-type receptor (such compounds are termed third generation EGFR tyrosine kinase inhibitors) [3]. It has been developed to overcome acquired resistance to, and side-effect liabilities of first and second generation EGFR inhibitors in non-small-cell lung cancer (NSCLC). Small-molecule EGFR T790M inhibitors and the development of novel compounds in the discovery pipeline are reviewed by Song et al. (2016) [5].
EGF816 is claimed in Novartis' patent WO2015085482 [4], where it is named (R,E)-N-(7-chloro-l-(l-(4-(dimethylamino)but-2-enoyl)azepan-3-yl)-lH-benzo[d]imidazol-2-yl)-2-methylisonicotinamide, which resolves to the IUPAC name presented here.
Preclinical characterisation is reported in [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 83.36
Molecular weight 494.22
XLogP 3.44
No. Lipinski's rules broken 0
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Canonical SMILES CN(CC=CC(=O)N1CCCCC(C1)n1c(NC(=O)c2ccnc(c2)C)nc2c1c(Cl)ccc2)C
Isomeric SMILES CN(C/C=C/C(=O)N1CCCC[C@H](C1)n1c(NC(=O)c2ccnc(c2)C)nc2c1c(Cl)ccc2)C
InChI InChI=1S/C26H31ClN6O2/c1-18-16-19(12-13-28-18)25(35)30-26-29-22-10-6-9-21(27)24(22)33(26)20-8-4-5-15-32(17-20)23(34)11-7-14-31(2)3/h6-7,9-13,16,20H,4-5,8,14-15,17H2,1-3H3,(H,29,30,35)/b11-7+/t20-/m1/s1
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
10259 nazartinib
Synonyms Click here for help
compound 47 [PMID: 27433829] | EGF-816 | EGF816
Database Links Click here for help
GtoPdb PubChem SID 315661280
PubChem CID 72703790
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