1N1

N-(2-CHLORO-6-METHYLPHENYL)-2-({6-[4-(2-HYDROXYETHYL)PIPERAZIN-1-YL]-2-METHYLPYRIMIDIN-4-YL}AMINO)-1,3-THIAZOLE-5-CARBOXAMIDE

Created: 2006-04-24
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count59
Chiral Atom Count0
Bond Count62
Aromatic Bond Count17
2D diagram of 1N1
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Chemical Component Summary

NameN-(2-CHLORO-6-METHYLPHENYL)-2-({6-[4-(2-HYDROXYETHYL)PIPERAZIN-1-YL]-2-METHYLPYRIMIDIN-4-YL}AMINO)-1,3-THIAZOLE-5-CARBOXAMIDE
SynonymsDasatinib
Systematic Name (OpenEye OEToolkits)N-(2-chloranyl-6-methyl-phenyl)-2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methyl-pyrimidin-4-yl]amino]-1,3-thiazole-5-carboxamide
FormulaC22 H26 Cl N7 O2 S
Molecular Weight488.006
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01Clc1cccc(c1NC(=O)c2sc(nc2)Nc4nc(nc(N3CCN(CCO)CC3)c4)C)C
SMILESCACTVS3.370Cc1nc(Nc2sc(cn2)C(=O)Nc3c(C)cccc3Cl)cc(n1)N4CCN(CCO)CC4
SMILESOpenEye OEToolkits1.7.2Cc1cccc(c1NC(=O)c2cnc(s2)Nc3cc(nc(n3)C)N4CCN(CC4)CCO)Cl
Canonical SMILESCACTVS3.370 Cc1nc(Nc2sc(cn2)C(=O)Nc3c(C)cccc3Cl)cc(n1)N4CCN(CCO)CC4
Canonical SMILESOpenEye OEToolkits1.7.2 Cc1cccc(c1NC(=O)c2cnc(s2)Nc3cc(nc(n3)C)N4CCN(CC4)CCO)Cl
InChIInChI1.03 InChI=1S/C22H26ClN7O2S/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27)
InChIKeyInChI1.03 ZBNZXTGUTAYRHI-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB01254 
NameDasatinib
Groups
  • approved
  • investigational
DescriptionDasatinib is an orally available multikinase inhibitor indicated for the treatment of Philadelphia chromosome (Ph)-positive leukemias.[A2224,L45171] Ph is a chromosomal abnormality found in patients with chronic myelogenous leukemia (CML) and acute lymphocytic leukemia (ALL), where the ABL tyrosine kinase and the breakpoint cluster region (BCR) gene transcribe the chimeric protein BCR-ABL. BCR-ABL is associated with the uncontrolled activity of the ABL tyrosine kinase and is involved in the pathogenesis of CML and 15-30% of ALL cases.[A11377,A33432] Dasatinib also inhibits a spectrum of kinases involved in cancer, including several SRC-family kinases.[A11377] Unlike [imatinib], another tyrosine kinase used for the treatment of CML and Ph-positive ALL, dasatinib inhibits the active and inactive conformations of the ABL kinase domain.[A2226,A11377] Also, mutations in the kinase domain of BCR-ABL may lead to relapse during imatinib treatment. Since dasatinib does not interact with some of the residues involved in those mutations, the use of this drug represents a therapeutic alternative for patients with cancers that have developed imatinib-resistance.[A2226] The use of dasatinib was first approved by the FDA in 2006.[L45171,L45186]
Synonyms
  • Dasatinib (anh.)
  • N-(2-CHLORO-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide
  • Dasatinib monohydrate
  • Dasatinib anhydrous
  • Dasatinib monolauryl sulfate
Brand Names
  • Dasatinib Accordpharma
  • Reddy-dasatinib
  • Taro-dasatinib
  • Apo-dasatinib
  • Teva-dasatinib
IndicationDasatinib is indicated for the treatment of newly diagnosed adults with Philadelphia chromosome-positive (Ph+) chronic myeloid leukemia (CML) in chronic phase, as well as adults with chronic, accelerated, or myeloid or lymphoid blast phase Ph+ CML with resistance or intolerance to prior therapy including imatinib, and adults with Philadelphia chromosome-positive acute lymphoblastic leukemia (Ph+ ALL) with resistance or intolerance to prior therapy. Dasatinib is also indicated for the treatment of pediatric patients 1 year of age and older with Ph+ CML in chronic phase or newly diagnosed Ph+ ALL in combination with chemotherapy.[L45171]
Categories
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • Bcr-Abl Tyrosine Kinase Inhibitors
  • BCRP/ABCG2 Inhibitors
  • BCRP/ABCG2 Substrates
ATC-CodeL01EA02
CAS number302962-49-8

Drug Targets

NameTarget SequencePharmacological ActionActions
Tyrosine-protein kinase ABL1MLEICLKLVGCKSKKGLSSSSSCYLEEALQRPVASDFEPQGLSEAARWNS...unknowninhibitor,multitarget
Proto-oncogene tyrosine-protein kinase SrcMGSNKSKPKDASQRRRSLEPAENVHGAGGGAFPASQTPSKPASADGHRGP...unknowninhibitor,multitarget
Ephrin type-A receptor 2MELQAARACFALLWGCALAAAAAAQGKEVVLLDFAAAGGELGWLTHPYGK...unknownantagonist
Tyrosine-protein kinase LckMGCGCSSHPEDDWMENIDVCENCHYPIVPLDGKGTLLIRNGSEVRDPLVT...unknowninhibitor,multitarget
Tyrosine-protein kinase YesMGCIKSKENKSPAIKYRPENTPEPVSTSVSHYGAEPTTVSPCPSSSAKGT...unknowninhibitor
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 CHEMBL1421
PubChem 3062316
ChEMBL CHEMBL1421
ChEBI CHEBI:49375
CCDC/CSD VECYUB