CHEBI:45783 - imatinib

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ChEBI Name imatinib
ChEBI ID CHEBI:45783
Definition A benzamide obtained by formal condensation of the carboxy group of 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid with the primary aromatic amino group of 4-methyl-N3-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,3-diamine. Used (as its mesylate salt) for treatment of chronic myelogenous leukemia and gastrointestinal stromal tumours.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:305376, CHEBI:38918, CHEBI:45781
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Formula C29H31N7O
Net Charge 0
Average Mass 493.60270
Monoisotopic Mass 493.259
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)
InChIKey KTUFNOKKBVMGRW-UHFFFAOYSA-N
SMILES CN1CCN(Cc2ccc(cc2)C(=O)Nc2ccc(C)c(Nc3nccc(n3)-c3cccnc3)c2)CC1
Roles Classification
Biological Role(s): apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
tyrosine kinase inhibitor
Any protein kinase inhibitor that interferes with the action of tyrosine kinase.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing imatinib (CHEBI:45783) has functional parent benzamide (CHEBI:28179)
imatinib (CHEBI:45783) has role antineoplastic agent (CHEBI:35610)
imatinib (CHEBI:45783) has role apoptosis inducer (CHEBI:68495)
imatinib (CHEBI:45783) has role tyrosine kinase inhibitor (CHEBI:38637)
imatinib (CHEBI:45783) is a N-methylpiperazine (CHEBI:46920)
imatinib (CHEBI:45783) is a aromatic amine (CHEBI:33860)
imatinib (CHEBI:45783) is a benzamides (CHEBI:22702)
imatinib (CHEBI:45783) is a pyridines (CHEBI:26421)
imatinib (CHEBI:45783) is a pyrimidines (CHEBI:39447)
Incoming linkable imatinib analogue (CHEBI:39083) has functional parent imatinib (CHEBI:45783)
imatinib methanesulfonate (CHEBI:31690) has part imatinib (CHEBI:45783)
IUPAC Name
4-[(4-methylpiperazin-1-yl)methyl]-N-{4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl}benzamide
INN Source
imatinib ChemIDplus
Synonyms Sources
4-(4-METHYL-PIPERAZIN-1-YLMETHYL)-N-[4-METHYL-3-(4-PYRIDIN-3-YL-PYRIMIDIN-2-YLAMINO)-PHENYL]-BENZAMIDE PDBeChem
α-(4-methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-toluidide ChemIDplus
STI 571 ChemIDplus
Database Links Databases
D08066 KEGG DRUG
DB00619 DrugBank
EP564409 Patent
HMDB14757 HMDB
Imatinib Wikipedia
LSM-1023 LINCS
STI PDBeChem
US5521184 Patent
View more database links
Registry Numbers Types Sources
152459-95-5 CAS Registry Number ChemIDplus
7671333 Beilstein Registry Number Beilstein
7671333 Reaxys Registry Number Reaxys
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Last Modified
24 February 2016
General Comment
2007-08-17 See: Zimmermann, J., Buchdunger, E., Mett, H., Meyer, T. and Lydon, N.B. (1997) Potent and selective inhibitors of the Abl-kinase: phenylamino-pyrimidine (PAP) derivatives. Bioorg. Med. Chem. Lett. 7, 187-192. [DOI:10.1016/S0960-894X(96)00601-4]