Imatinib (CHEM022147)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:21:38 UTC
Update Date2016-11-09 01:17:26 UTC
Accession NumberCHEM022147
Identification
Common NameImatinib
ClassSmall Molecule
DescriptionA 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-N(3)-[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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01bd-9863300000-bf69c843c9ad9179bcdbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0000900000-3974d719909aa7a75039Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0000900000-dd386ae17930da36c11fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0f6x-0159500000-576f293e026deaa1ec7fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0ik9-0495000000-06102c4afd3c2e88cf87Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03ka-0971000000-b487f693e17cba198e37Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-05fs-0930000000-9319811c561fd5cc8f2fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0159-4910000000-25480eb9451aee843c26Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-9000000000-0638bee21655c0e0ca00Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-9000000000-76f9b62b017fe8241e67Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0006-0000900000-3974d719909aa7a75039Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0f6x-0159500000-f0cc13bf8cf30039ba42Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-0000900000-0500d51bcaafb965101aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-0000900000-418060192cf47ec8c870Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0ik9-0495000000-7a5a72b785a749af3a4aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-0036900000-e06abe669a9b1b57e2c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0000900000-9825e12c65f9bf36d72fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-1029200000-acd76280414e767f0280Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-2269000000-f55e5c707c9de5ba2d0fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00ba-3494000000-19e7d8361f050ec8b637Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00ba-3693000000-c1e011113081e3341bbaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0596-5981000000-a0f689cd067d45644bcdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0f9f-5930000000-71f05e812cf29e11cc69Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00ku-5910000000-3f91ea6a6f7402767a78Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-029i-7900000000-507c771376ea4b799b6dSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0191000000-fb24a3158c9475186c82Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14660054
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14715630
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15073101
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15170967
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15722647
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15794712
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15966213
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16122278
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16826359
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16983347
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17190842
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=17410337
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=17457302
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=17717205
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=18193246
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=18216472
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=18337118
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=18344535
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=18376233
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=18407734
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=18420270
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=18423008
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=18548219
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=18623899
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=18780518
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=18809244
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=19020005
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=19052981
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=19077095
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=19097599
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=19182535
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=19242505
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=19415889
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=19527930
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=19591692
36. https://www.ncbi.nlm.nih.gov/pubmed/?term=19693287
37. https://www.ncbi.nlm.nih.gov/pubmed/?term=19749465
38. https://www.ncbi.nlm.nih.gov/pubmed/?term=19810774
39. https://www.ncbi.nlm.nih.gov/pubmed/?term=19853594
40. https://www.ncbi.nlm.nih.gov/pubmed/?term=19920908
41. https://www.ncbi.nlm.nih.gov/pubmed/?term=22891806
42. https://www.ncbi.nlm.nih.gov/pubmed/?term=23075630
43. https://www.ncbi.nlm.nih.gov/pubmed/?term=23183914
44. https://www.ncbi.nlm.nih.gov/pubmed/?term=23313020
45. https://www.ncbi.nlm.nih.gov/pubmed/?term=23394269
46. https://www.ncbi.nlm.nih.gov/pubmed/?term=23480638
47. https://www.ncbi.nlm.nih.gov/pubmed/?term=23503753
48. https://www.ncbi.nlm.nih.gov/pubmed/?term=23536338
49. https://www.ncbi.nlm.nih.gov/pubmed/?term=23574742
50. https://www.ncbi.nlm.nih.gov/pubmed/?term=23580311
51. https://www.ncbi.nlm.nih.gov/pubmed/?term=23587588
52. Vigneri P, Wang JY: Induction of apoptosis in chronic myelogenous leukemia cells through nuclear entrapment of BCR-ABL tyrosine kinase. Nat Med. 2001 Feb;7(2):228-34.
53. Deininger MW, Druker BJ: Specific targeted therapy of chronic myelogenous leukemia with imatinib. Pharmacol Rev. 2003 Sep;55(3):401-23. Epub 2003 Jul 17.
54. Lassila M, Allen TJ, Cao Z, Thallas V, Jandeleit-Dahm KA, Candido R, Cooper ME: Imatinib attenuates diabetes-associated atherosclerosis. Arterioscler Thromb Vasc Biol. 2004 May;24(5):935-42. Epub 2004 Feb 26.
55. Reeves PM, Bommarius B, Lebeis S, McNulty S, Christensen J, Swimm A, Chahroudi A, Chavan R, Feinberg MB, Veach D, Bornmann W, Sherman M, Kalman D: Disabling poxvirus pathogenesis by inhibition of Abl-family tyrosine kinases. Nat Med. 2005 Jul;11(7):731-9. Epub 2005 Jun 26.
56. Droogendijk HJ, Kluin-Nelemans HJ, van Doormaal JJ, Oranje AP, van de Loosdrecht AA, van Daele PL: Imatinib mesylate in the treatment of systemic mastocytosis: a phase II trial. Cancer. 2006 Jul 15;107(2):345-51.