STI

4-(4-METHYL-PIPERAZIN-1-YLMETHYL)-N-[4-METHYL-3-(4-PYRIDIN-3-YL-PYRIMIDIN-2-YLAMINO)-PHENYL]-BENZAMIDE

Created:2001-04-11
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count68
Chiral Atom Count0
Bond Count72
Aromatic Bond Count25
2D diagram of STI

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Chemical Component Summary

Name4-(4-METHYL-PIPERAZIN-1-YLMETHYL)-N-[4-METHYL-3-(4-PYRIDIN-3-YL-PYRIMIDIN-2-YLAMINO)-PHENYL]-BENZAMIDE
SynonymsSTI-571; IMATINIB
Systematic Name (OpenEye OEToolkits)4-[(4-methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide
FormulaC29 H31 N7 O
Molecular Weight493.603
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs10.04O=C(Nc3ccc(c(Nc2nc(c1cccnc1)ccn2)c3)C)c4ccc(cc4)CN5CCN(CC5)C
SMILESCACTVS3.341CN1CCN(CC1)Cc2ccc(cc2)C(=O)Nc3ccc(C)c(Nc4nccc(n4)c5cccnc5)c3
SMILESOpenEye OEToolkits1.5.0Cc1ccc(cc1Nc2nccc(n2)c3cccnc3)NC(=O)c4ccc(cc4)CN5CCN(CC5)C
Canonical SMILESCACTVS3.341 CN1CCN(CC1)Cc2ccc(cc2)C(=O)Nc3ccc(C)c(Nc4nccc(n4)c5cccnc5)c3
Canonical SMILESOpenEye OEToolkits1.5.0 Cc1ccc(cc1Nc2nccc(n2)c3cccnc3)NC(=O)c4ccc(cc4)CN5CCN(CC5)C
InChIInChI1.03 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)
InChIKeyInChI1.03 KTUFNOKKBVMGRW-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB00619 
NameImatinib
Groups approved
DescriptionImatinib is a small molecule kinase inhibitor that revolutionized the treatment of cancer, particularly chronic myeloid leukemia, in 2001.[A249305] It was deemed a "miracle drug" due to its clinical success, as oncologist Dr. Brian noted that "complete hematologic responses were observed in 53 of 54 patients with CML treated with a daily dosage of 300 mg or more and typically occurred in the first four weeks of therapy".[A249315]. The discovery of imatinib also established a new group of therapy called "targeted therapy", since treatment can be tailored specifically to the unique cancer genetics of each patient.[L42220] Imatinib was approved on February 1st ,2001 by the FDA and November 7th, 2001 by the EMA; however, its European approval has been withdrawn in October 2023.[A263036,L49746,L49751]
Synonyms
  • Imatinib
  • Imatinibum
  • Imatinib mesylate
  • α-(4-methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-toluidide
Brand Names
  • Imatinib Koanaa
  • Imatinib Teva
  • Glivec
  • Ach-imatinib
  • Imatinib mesylate
IndicationImatinib is indicated for the treatment of adult and pediatric chronic myeloid leukemia with Philadelphia chromosome mutation (Ph+) in blast crisis, accelerated phase, or chronic phase after IFN-alpha therapy failure.[L42080] Additionally, imatinib is also indicated to treat adult and pediatric Ph+ acute lymphoblastic leukemia, adult myelodysplastic/myeloproliferative diseases, adult aggressive systemic mastocytosis, adult hypereosinophilic syndrome and/or chronic eosinophilic leukemia (CEL), adult dermatofibrosarcoma protuberans, and malignant gastrointestinal stromal tumors (GIST).[L42080]
Categories
  • Amides
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • Bcr-Abl Tyrosine Kinase Inhibitors
  • BCRP/ABCG2 Inhibitors
ATC-CodeL01EA01
CAS number152459-95-5

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Breakpoint cluster region proteinMVDPVGFAEAWKAQFPDSEPPRMELRSVGDIEQELERCKASIRRLEQEVN...unknowninhibitor
Induced myeloid leukemia cell differentiation protein Mcl-1MFGLKRNAVIGLNLYCGGAGLGAGSGGATRPGGRLLATEKEASARREIGG...unknownother/unknown
Mast/stem cell growth factor receptor KitMRGARGAWDFLCVLLLLLRVQTGSSQPSVSPGEPSPPSIHPGKSDLIVRV...unknownantagonist
Proto-oncogene tyrosine-protein kinase receptor RetMAKATSGAAGLRLLLLLLLPLLGKVALGLYFSRDAYWEKLYVDQAAGTPL...unknowninhibitor
Platelet-derived growth factor receptor alphaMGTSHPAFLVLGCLLTGLSLILCQLSLPSILPNENEKVVQLNSSFSLRCF...unknownantagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL941
PubChem 5291
ChEMBL CHEMBL941
ChEBI CHEBI:45783
CCDC/CSD XAVTOF02, XAVTOF03, XEJLUW, XAVTOF, DUNTIQ, XAVTOF04, CAPVAU, CAPVEY, CAPVOI