imatinib   Click here for help

GtoPdb Ligand ID: 5687

Synonyms: CGP 57148 | Gleevec® | Glivec® | STI571
Approved drug PDB Ligand Immunopharmacology Ligand
imatinib is an approved drug (FDA & EMA (2001))
Compound class: Synthetic organic
Comment: Imatinib is a Type-2 kinase inhibitor. Its main inhibitory activity is against ABL kinase, but it has significant action at secondary targets including platelet-derived growth factor receptor (PDGFR) and stem cell growth factor receptor (KIT).

Coronavirus: imatinib is reported to block Spike protein-induced SARS-CoV and MERS-CoV fusion in vitro [8], potentially by blocking Abl2 at the endosomal membrane and disrupting the actin dynamics that are required for virus-host fusion [2]. It will be informative to determine if this holds true for SARS-CoV-2, and whether re-purposing of imatinib and/or newer Abl kinase inhibitors (dasatinib, bosutinib, ponatinib, nilotinib) could be a viable strategy against COVID-19. This approach would likely to be most effective during the early stage of infection.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 86.28
Molecular weight 493.26
XLogP 3.04
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CN1CCN(CC1)Cc1ccc(cc1)C(=O)Nc1ccc(c(c1)Nc1nccc(n1)c1cccnc1)C
Isomeric SMILES CN1CCN(CC1)Cc1ccc(cc1)C(=O)Nc1ccc(c(c1)Nc1nccc(n1)c1cccnc1)C
InChI InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)
InChI Key KTUFNOKKBVMGRW-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA & EMA (2001))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)-4-[(4-methylpiperazin-1-yl)methyl]benzamide
International Nonproprietary Names Click here for help
INN number INN
8031 imatinib
Synonyms Click here for help
CGP 57148 | Gleevec® | Glivec® | STI571
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9659761
Reactome Reaction Reactome logo R-HSA-9669854, R-HSA-9669900, R-HSA-9674430, R-HSA-9674095, R-HSA-9669859, R-HSA-9674397
Other databases
CAS Registry No. 152459-95-5
ChEBI CHEBI:45783
ChEMBL Ligand CHEMBL941
DrugBank Ligand DB00619
DrugCentral Ligand 1423
GtoPdb PubChem SID 178102314
PubChem CID 5291
RCSB PDB Ligand STI
Search Google for chemical match using the InChIKey KTUFNOKKBVMGRW-UHFFFAOYSA-N
Search Google for chemicals with the same backbone KTUFNOKKBVMGRW
Search PubMed clinical trials imatinib
Search PubMed titles imatinib
Search PubMed titles/abstracts imatinib
SynPHARM 78741 (in complex with ABL proto-oncogene 1, non-receptor tyrosine kinase)
UniChem Compound Search for chemical match using the InChIKey KTUFNOKKBVMGRW-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey KTUFNOKKBVMGRW-UHFFFAOYSA-N
Wikipedia Imatinib