Imatinib (CED0001322)

Record Information
Version1.0
Creation Date2016-05-25 18:21:38 UTC
Update Date2026-08-22 08:59:28 UTC
Accession NumberCHEM022147
Identification
Common NameImatinib
ClassSmall Molecule
Description
Imatinib is an organic compound with the formula C29H31N7O and an average molecular weight of 493.60 g/mol. Imatinib belongs to the anilides, a subclass of benzene and substituted derivatives within the organic compounds. This compound acts as an antagonist, inhibitor, or unknown modulator for ten recorded protein targets, including Tyrosine-protein kinase ABL1, Platelet-derived growth factor receptor beta (PDGFRB), Proto-oncogene tyrosine-protein kinase receptor Ret (RET), and Mast/stem cell growth factor receptor Kit (KIT). In clinical applications, imatinib is used as a treatment for leukemia (PMC9565840), cancer (PMC6052860, PMC7609673), and glioblastoma (PMC7226512). Specifically, it is used to treat acute lymphoblastic leukemia (PMC4012724) and chronic myeloid leukemia (PMC4243416, PMC4512945, PMC7527863), with the latter also being associated with the compound (PMC8487861) and showing a therapeutic effect (PMC9368267). Additionally, it has a therapeutic effect on pancreatic cancer (PMC8122931). Imatinib has been found in or released from 28 recorded sources. These include aquatic systems and sediments such as seawater, freshwater, groundwater, and surface water; drinking water and water supply sources including bottled, tap, desalinated, and drinking water; and wastewater, sanitation, and biosolids, including industrial wastewater, mine wastewater, wastewater treatment effluent, and unspecified wastewater. It is also found in appliances, HVAC, and refrigerants such as water heaters and water coolers; household cleaning and consumer products including tobacco pipes, tobacco smoke filters, and non-electric simulated smoking devices; and electrical and electronic equipment, including electrodes, fixed capacitors and their manufacture, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials, as well as 6 more sectors. Recorded exposure routes include touch, oral, and inhalation.
Contaminant Type
  • PMT
Chemical Structure
Synonyms
ValueSource
4-(4-METHYL-piperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamideChEBI
alpha-(4-Methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-toluidideChEBI
STI 571ChEBI
GlamoxKegg
a-(4-Methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-toluidideGenerator
Α-(4-methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-toluidideGenerator
Imatinib methansulfonateHMDB
STI-571HMDB
GlivecHMDB
Methanesulfonate, imatinibHMDB
Imatinib methanesulfonateHMDB
Imatinib mesylateHMDB
GleevecHMDB
Mesylate, imatinibHMDB
alpha-(4-Methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-tolu-p-toluidideHMDB
Chemical FormulaC29H31N7O
Average Molecular Mass493.603 g/mol
Monoisotopic Mass493.259 g/mol
CAS Registry Number152459-95-5
IUPAC NameN-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)-4-[(4-methylpiperazin-1-yl)methyl]benzamide
Traditional Nameimatinib
SMILESCN1CCN(CC2=CC=C(C=C2)C(=O)NC2=CC(NC3=NC=CC(=N3)C3=CN=CC=C3)=C(C)C=C2)CC1
InChI IdentifierInChI=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 KeyKTUFNOKKBVMGRW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxazolidinediones. Oxazolidinediones are compounds containing an oxazolidine ring which bears two ketones.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassOxazolidines
Direct ParentOxazolidinediones
Alternative Parents
Substituents
  • Oxazolidinedione
  • Dicarboximide
  • Carbamic acid ester
  • Carbonic acid derivative
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP3.47ALOGPS
logP4.38ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)8.27ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.28 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity148.93 m³·mol⁻¹ChemAxon
Polarizability55.54 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-01bd-9863300000-bf69c843c9ad9179bcdbNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0036900000-e06abe669a9b1b57e2c3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0000900000-3974d719909aa7a75039Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0000900000-dd386ae17930da36c11fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f6x-0159500000-576f293e026deaa1ec7fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ik9-0495000000-06102c4afd3c2e88cf87Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03ka-0971000000-b487f693e17cba198e37Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05fs-0930000000-9319811c561fd5cc8f2fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0159-4910000000-25480eb9451aee843c26Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9000000000-0638bee21655c0e0ca00Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9000000000-76f9b62b017fe8241e67Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0000900000-9825e12c65f9bf36d72fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-1029200000-acd76280414e767f0280Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-2269000000-f55e5c707c9de5ba2d0fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ba-3494000000-19e7d8361f050ec8b637Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ba-3693000000-c1e011113081e3341bbaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0596-5981000000-a0f689cd067d45644bcdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f9f-5930000000-71f05e812cf29e11cc69Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ku-5910000000-3f91ea6a6f7402767a78Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-029i-7900000000-507c771376ea4b799b6dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0191000000-fb24a3158c9475186c82Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0036900000-e06abe669a9b1b57e2c3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-3379600000-f122458b106bcf2c8b8eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-2269000000-5f7e9af0d9c9de6feb49Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ba-3494000000-d9e8bb9ec5fbc205011dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-1029200000-43996111f43301404fc5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0000900000-65b7037c703bd3c241aaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-3269700000-8eec56a5a4bb77f1b128Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0000900000-3974d719909aa7a75039Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f6x-0159500000-f0cc13bf8cf30039ba42Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0000900000-0500d51bcaafb965101aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0029500000-e167f1a0cef2a4f188b3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0029000000-a41da1f0dcbe55203ab0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0097-0198000000-65ebb8699c243213792eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0000900000-45964b01e9deaf4c93e5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0001900000-6b67e224bf0dee869ce0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0000900000-418060192cf47ec8c870Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0049700000-48b39fb21d042f6f9ea8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ik9-0495000000-7a5a72b785a749af3a4aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0144900000-2c1268fe741d4e07f7a4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-0698300000-b23d90ff38472b542f79Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02tc-3911000000-88d44a81ccb6cf024cbcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1110900000-e7ed25c6dc02f44eff1eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002g-7534900000-56f8e35b9d7416fcc95fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9610100000-772d808632d87b2ad3e5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0001900000-a99288610636d0dfa341Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-0319200000-fa01307dc8a37103d1ceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-2902300000-500fd23bf53833b6d895Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0000900000-2594568be09b0be69e31Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0002900000-6c2516b6d44b11d2a96eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0209-0131900000-9cfd6cd2504e399080f9Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1174.0Log mg/kg[660:2100]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
canceris_treatment_forNot AvailablePMC6052860 , PMC7609673
leukemiais_treatment_forNot AvailablePMC9565840
glioblastomais_treatment_forNot AvailablePMC7226512
chronic myeloid leukemiais_treatment_forNot AvailablePMC4243416 , PMC4512945 , PMC7527863
chronic myeloid leukemiaassociated_withNot AvailablePMC8487861
chronic myeloid leukemiahas_therapeutic_effect_onNot AvailablePMC9368267
acute lymphoblastic leukemiais_treatment_forNot AvailablePMC4012724
pancreatic cancerhas_therapeutic_effect_onNot AvailablePMC8122931
vitiligoassociated_withNot AvailablePMC11204138 , PMC11204138
chronic eosinophilic leukemiais_treatment_forNot AvailablePMC10580003
Exposure Sources
Source IDSourceSectorReference
3Irrigation waterAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
27Water CoolersAppliances, HVAC & refrigerantsNot Available
43Water heatersAppliances, HVAC & refrigerantsNot Available
50GroundwaterAquatic systems & sedimentsNot Available
51Surface waterAquatic systems & sedimentsNot Available
52SeawaterAquatic systems & sedimentsNot Available
53FreshwaterAquatic systems & sedimentsNot Available
70Stormwater runoffAutomotive & urban infrastructureNot Available
88Waterproofing spraysBuilding & ConstructionNot Available
115Drinking waterDrinking water & water supplyNot Available
116Tap waterDrinking water & water supplyNot Available
117Bottled waterDrinking water & water supplyNot Available
118Desalinated waterDrinking water & water supplyNot Available
181Ballast waterMarine, shipping & aquacultureNot Available
182Bilge waterMarine, shipping & aquacultureNot Available
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
468Industrial wastewaterWastewater, sanitation & biosolidsNot Available
470Wastewater treatment effluentWastewater, sanitation & biosolidsNot Available
475Mine wastewaterWastewater, sanitation & biosolidsNot Available
477Wastewater, unspecifiedWastewater, sanitation & biosolidsNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Tyrosine-protein kinase ABL1 structureClick to view 3D structureTyrosine-protein kinase ABL1P00519HumansPredicted (SEA)0.389246
Mast/stem cell growth factor receptor Kit structureClick to view 3D structureMast/stem cell growth factor receptor KitP10721HumansPredicted (SEA)0.934191
Platelet-derived growth factor receptor beta structureClick to view 3D structurePlatelet-derived growth factor receptor betaP09619HumansPredicted (SEA)0.934191
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)2.95827
Breakpoint cluster region protein structureClick to view 3D structureBreakpoint cluster region proteinP11274HumansPredicted (SEA)0.0778492
Tyrosine-protein kinase ABL2 structureClick to view 3D structureTyrosine-protein kinase ABL2P42684HumansPredicted (SEA)0.0778492
Tyrosine-protein kinase Lyn structureClick to view 3D structureTyrosine-protein kinase LynP07948HumansPredicted (SEA)2.02408
Tyrosine-protein kinase SYK structureClick to view 3D structureTyrosine-protein kinase SYKP43405HumansPredicted (SEA)2.41333
Platelet-derived growth factor receptor alpha structureClick to view 3D structurePlatelet-derived growth factor receptor alphaP16234HumansPredicted (SEA)1.08989
Epithelial discoidin domain-containing receptor 1 structureClick to view 3D structureEpithelial discoidin domain-containing receptor 1Q08345HumansPredicted (SEA)0.0778492
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)5.44945
Mitogen-activated protein kinase 14 structureClick to view 3D structureMitogen-activated protein kinase 14Q16539HumansPredicted (SEA)3.19182
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)9.6533
Discoidin domain-containing receptor 2 structureClick to view 3D structureDiscoidin domain-containing receptor 2Q16832HumansPredicted (SEA)0.155698
Receptor-type tyrosine-protein kinase FLT3 structureClick to view 3D structureReceptor-type tyrosine-protein kinase FLT3P36888HumansPredicted (SEA)8.79696
Macrophage colony-stimulating factor 1 receptor structureClick to view 3D structureMacrophage colony-stimulating factor 1 receptorP07333HumansPredicted (SEA)3.65891
Serine/threonine-protein kinase B-raf structureClick to view 3D structureSerine/threonine-protein kinase B-rafP15056HumansPredicted (SEA)1.79053
Interleukin-1 receptor-associated kinase 1 structureClick to view 3D structureInterleukin-1 receptor-associated kinase 1P51617HumansPredicted (SEA)1.63483
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)11.8331
Receptor tyrosine-protein kinase erbB-4 structureClick to view 3D structureReceptor tyrosine-protein kinase erbB-4Q15303HumansPredicted (SEA)4.5931
Tyrosine-protein kinase Fyn structureClick to view 3D structureTyrosine-protein kinase FynP06241HumansPredicted (SEA)5.2159
Proto-oncogene tyrosine-protein kinase receptor Ret structureClick to view 3D structureProto-oncogene tyrosine-protein kinase receptor RetP07949HumansPredicted (SEA)3.81461
Click to view 3D structureTyrosine-protein kinase FRKP42685HumansPredicted (SEA)3.19182
MAP kinase-activated protein kinase 2 structureClick to view 3D structureMAP kinase-activated protein kinase 2P49137HumansPredicted (SEA)2.80257
Ephrin type-A receptor 2 structureClick to view 3D structureEphrin type-A receptor 2P29317HumansPredicted (SEA)2.33548
Concentrations
Not Available
External Links
DrugBank IDDB00619
HMDB IDHMDB0014757
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDSTI
Wikipedia LinkImatinib
Chemspider ID5101
ChEBI ID45783
PubChem Compound ID5291
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
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