Chemical Component Summary

Name3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)pyridin-2-amine
SynonymsCRIZOTINIB
Identifiers3-[(1R)-1-(2,6-dichloro-3-fluoro-phenyl)ethoxy]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine
FormulaC21 H22 Cl2 F N5 O
Molecular Weight450.337
TypeNON-POLYMER
Isomeric SMILESC[C@H](c1c(ccc(c1Cl)F)Cl)Oc2cc(cnc2N)c3cnn(c3)C4CCNCC4
InChIInChI=1S/C21H22Cl2FN5O/c1-12(19-16(22)2-3-17(24)20(19)23)30-18-8-13(9-27-21(18)25)14-10-28-29(11-14)15-4-6-26-7-5-15/h2-3,8-12,15,26H,4-7H2,1H3,(H2,25,27)/t12-/m1/s1
InChIKeyKTEIFNKAUNYNJU-GFCCVEGCSA-N

Chemical Details

Formal Charge0
Atom Count52
Chiral Atom Count1
Bond Count55
Aromatic Bond Count18

Drug Info: DrugBank

DrugBank IDDB08865 
NameCrizotinib
Groups
  • investigational
  • approved
DescriptionCrizotinib is a tyrosine kinase receptor inhibitor used for the treatment of anaplastic lymphoma kinase (ALK) or ROS1-positive non-small cell lung cancer (NSCLC) tumors, as well as ALK-positive anaplastic large cell lymphoma (ALCL) and inflammatory myofibroblastic tumor (IMT).[L42460] By targeting the echinoderm microtubule-associated protein-like 4 (EML4)-ALK fusion protein, crizotinib offers robust effectiveness in treating NSCLC in patients with this type of rearrangement.[A250785] Crizotinib was the first-in-class drug used to treat ALK-positive tumors. Second- and third-generation ALK-tyrosine kinase-inhibitors have overcome many of the pharmacodynamic and genetic resistance mechanisms crizotinib is prone to.[A250785] Crizotinib was approved by the FDA in 2011, and its use is accompanied by FDA-approved tests used to detect ALK and ROS1 rearrangements.[L42460]
Synonyms
  • Crizotinibum
  • (R)-crizotinib
  • Crizotinib
Brand NamesXalkori
IndicationCrizotinib is a kinase inhibitor indicated for the treatment of patients with metastatic non-small cell lung cancer (NSCLC) whose tumors are anaplastic lymphoma kinase (ALK) or ROS1-positive as detected by an FDA-approved test.[L42460] Crizotinib is also indicated for the treatment of relapsed or refractory, systemic anaplastic large cell lymphoma (ALCL) that is ALK-positive in pediatric patients 1 year of age and older and young adults. The safety and efficacy of crizotinib have not been established in older adults with relapsed or refractory, systemic ALK-positive ALCL.[L42460] Additionally, crizotinib is indicated for the treatment of adult and pediatric patients 1 year of age and older with unresectable, recurrent, or refractory inflammatory myofibroblastic tumor (IMT) that is ALK-positive.[L42460]
Categories
  • Aminopyridines
  • Anaplastic lymphoma kinase (ALK) inhibitors
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • Bradycardia-Causing Agents
ATC-CodeL01ED01
CAS number877399-52-5

Drug Targets

NameTarget SequencePharmacological ActionActions
ALK tyrosine kinase receptorMGAIGLLWLLPLLLSTAAVGSGMGTGQRAGSPAAGPPLQPREPLSYSRLQ...unknowninhibitor
Hepatocyte growth factor receptorMKAPAVLAPGILVLLFTLVQRSNGECKEALAKSEMNVNMKYQLPNFTAET...unknowninhibitor
Proto-oncogene tyrosine-protein kinase ROSMKNIYCLIPKLVNFATLGCLWISVVQCTVLNSCLKSCVTNLGQQLDLGTP...unknowninhibitor
Macrophage-stimulating protein receptorMELLPPLPQSFLLLLLLPAKPAAGEDWQCPRTPYAASRDFDVKYVVPSFS...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor
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 CHEMBL601719
PubChem 11626560
ChEMBL CHEMBL601719
ChEBI CHEBI:64310
CCDC/CSD JURZOO, JURZOO01