You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:17 UTC
Secondary Accession Numbers
  • HMDB14757
Metabolite Identification
Common NameImatinib
DescriptionImatinib, also known as STI 571 or glamox, belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene. Imatinib is a drug which is used for the treatment of philadelphia chromosome positive chronic myeloid leukemia (ph+ cml), ph+ acute lymphoblastic leukaemia, myelodysplastic/myeloproliferative diseases, aggressive systemic mastocytosis, hypereosinophilic syndrome and/or chronic eosinophilic leukemia (cel), dermatofibrosarcoma protuberans, and malignant gastrointestinal stromal tumors (gist). Imatinib is a very strong basic compound (based on its pKa). It is currently marketed by Novartis as Imatinib (USA) or Imatinib (Europe/Australia) as its mesylate salt, imatinib mesilate (INN). Within humans, imatinib participates in a number of enzymatic reactions. In particular, imatinib can be converted into imatinib through the action of the enzyme solute carrier family 22 member 1. In addition, imatinib can be converted into imatinib; which is mediated by the enzyme multidrug resistance protein 1. In humans, imatinib is involved in imatinib inhibition of bcr-abl. BCR-ABL generates a fusion protein that acts as a constitutively active tyrosine kinase and imatinib works to inhibit this constitutive enzymatic activity. This metabolite is similar in potency to the parent compound. It is used in treating chronic myelogenous leukemia (CML), gastrointestinal stromal tumors (GISTs) and a number of other malignancies.
Imatinib methansulfonateHMDB
Methanesulfonate, imatinibHMDB
Imatinib methanesulfonateHMDB
Imatinib mesylateHMDB
Mesylate, imatinibHMDB
Chemical FormulaC29H31N7O
Average Molecular Weight493.6027
Monoisotopic Molecular Weight493.259008649
IUPAC NameN-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)-4-[(4-methylpiperazin-1-yl)methyl]benzamide
Traditional Nameimatinib
CAS Registry Number152459-95-5
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentBenzanilides
Alternative Parents
  • Benzanilide
  • Pyridinylpyrimidine
  • Benzamide
  • Benzoic acid or derivatives
  • Diaminotoluene
  • Phenylmethylamine
  • Benzoyl
  • Benzylamine
  • Aniline or substituted anilines
  • Aminopyrimidine
  • Aralkylamine
  • Toluene
  • N-alkylpiperazine
  • N-methylpiperazine
  • 1,4-diazinane
  • Pyridine
  • Piperazine
  • Pyrimidine
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxamide group
  • Amino acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Secondary amine
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Biological location:


Naturally occurring process:


Industrial application:

Physical Properties
Experimental Properties
Melting Point226 °C (mesylate salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility0.015 g/LNot Available
LogP3Not Available
Predicted Properties
Water Solubility0.015 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01bd-9863300000-bf69c843c9ad9179bcdbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-0036900000-e06abe669a9b1b57e2c3Spectrum
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 - 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0144900000-2c1268fe741d4e07f7a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-0698300000-b23d90ff38472b542f79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02tc-3911000000-88d44a81ccb6cf024cbcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1110900000-e7ed25c6dc02f44eff1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002g-7534900000-56f8e35b9d7416fcc95fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9610100000-772d808632d87b2ad3e5Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00619 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00619 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00619
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5101
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkImatinib
METLIN IDNot Available
PubChem Compound5291
ChEBI ID45783
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:11175855 ]
  2. 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. [PubMed:12869662 ]
  3. 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. [PubMed:14988091 ]
  4. 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. [PubMed:15980865 ]
  5. 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. [PubMed:16779792 ]