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imatinib (CHEBI:45783)

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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:45781, CHEBI:38918, CHEBI:305376
Supplier Information
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Formula Source
C29H31N7O ChEBI
Net Charge 0
Average Mass 493.60270
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
Chemical Role(s): tyrosine kinase inhibitor
Any protein kinase inhibitor that interferes with the action of tyrosine kinase.
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.
View more on the ChEBI Ontology
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
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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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]
 
Last Modified
16 June 2014

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