imatinib (CHEBI:45783)

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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

Supplier Information	ChemicalBook:CB22464309, Selleckchem:ly-411575, ZINC000028824948

Download	Molfile XML SDF

more structures >>

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M END): 24 ms

reading 68 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

68 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Jmol script terminated

Molfile expand

Wikipedia	License
Ecdysone is a prohormone of the major insect molting hormone 20-hydroxyecdysone, secreted from the prothoracic glands. It is of steroidal structure. Insect molting hormones (ecdysone and its homologues) are generally called ecdysteroids. Ecdysteroids act as moulting hormones of arthropods but also occur in other related phyla where they can play different roles. In Drosophila melanogaster, an increase in ecdysone concentration induces the expression of genes coding for proteins that the larva requires. It causes chromosome puffs (sites of high expression) to form in polytene chromosomes. Recent findings in the laboratory of Chris Q. Doe have found a novel role of this hormone in regulating temporal gene transitions within neural stem cells of the fruit fly. Ecdysone and other ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects. These phytoecdysteroids have been reputed to have medicinal value. They are part of herbal adaptogenic remedies like Cordyceps, yet an ecdysteroid precursor in plants has been shown to have cytotoxic properties as well as antioxidant properties on lipid peroxidation. Tebufenozide, sold under the Bayer trademark MIMIC, has ecdysteroid activity although its chemical structure has little resemblance to the ecdysteroids.
Read full article at Wikipedia

Formula

C29H31N7O

Net Charge

Average Mass

493.60270

Monoisotopic Mass

493.25901

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):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

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 via 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

Manual Xrefs	Databases
1423	DrugCentral
D08066	KEGG DRUG
DB00619	DrugBank
EP564409	Patent
HMDB0014757	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

Citations

Last Modified

22 February 2017

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]

CHEBI:45783 - imatinib

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