crizotinib (CED0002295)

Record Information
Version1.0
Creation Date2016-06-03 13:34:03 UTC
Update Date2026-05-14 19:00:15 UTC
Accession NumberCHEM045666
Identification
Common Namecrizotinib
ClassSmall Molecule
Description
Crizotinib is an organic compound with the formula C21H22Cl2FN5O and an average molecular weight of 450.34 g/mol. It is found in or released from healthcare, pharmaceuticals, and veterinary products, specifically as an antineoplastic agent, and is administered via the oral exposure route. crizotinib belongs to the pyrazolylpyridines, a subclass of pyridines and derivatives within the organic compounds. The compound functions as an inhibitor for four recorded protein targets: the ALK tyrosine kinase receptor, the Hepatocyte growth factor receptor (MET), the Proto-oncogene tyrosine-protein kinase ROS (ROS1), and the Macrophage-stimulating protein receptor (MST1R). It is classified within the superclass of organoheterocyclic compounds.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC21H22Cl2FN5O
Average Molecular Mass450.340 g/mol
Monoisotopic Mass449.119 g/mol
CAS Registry Number877399-52-5
IUPAC Name3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]pyridin-2-amine
Traditional Namecrizotinib
SMILESCC(OC1=C(N)N=CC(=C1)C1=CN(N=C1)C1CCNCC1)C1=C(Cl)C=CC(F)=C1Cl
InChI IdentifierInChI=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)
InChI KeyKTEIFNKAUNYNJU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrazolylpyridines. Pyrazolylpyridines are compounds containing a pyrazolylpyridine skeleton, which consists of a pyrazole linked (not fused) to a pyridine by a bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyrazolylpyridines
Direct ParentPyrazolylpyridines
Alternative Parents
Substituents
  • 3-pyrazolylpyridine
  • 1,3-dichlorobenzene
  • Alkyl aryl ether
  • Aminopyridine
  • Halobenzene
  • Fluorobenzene
  • Chlorobenzene
  • Aryl chloride
  • Aryl fluoride
  • Aryl halide
  • Imidolactam
  • Benzenoid
  • Monocyclic benzene moiety
  • Piperidine
  • Pyrazole
  • Azole
  • Heteroaromatic compound
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Ether
  • Organonitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Primary amine
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0061 g/LALOGPS
logP3.82ALOGPS
logP3.57ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)10.12ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area77.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity128.43 m³·mol⁻¹ChemAxon
Polarizability45.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001l-9420400000-925f9b3f3f45b0666591Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0020900000-233d907756fe4fceba4bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001u-1829000000-69f94a73792ae670873fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-6930000000-f08ea5767833ddc989ecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0120900000-dc95a63fa4e5933c0768Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052p-4168900000-d58ab2d73cfa3fdf140bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0597-3920000000-2aa2aa0675ab29af33cbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0000900000-a816d72754f8aab59a21Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0122900000-27e6152c0c91564dcebaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bvi-2942300000-1fe5a4ae12c4ea54a22fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0040900000-19bba22e0933ec4fe10cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-2491100000-c19536c52dbb054bbd8cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001l-9654400000-635215d033083c726602Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
990.0Log mg/kg[560:1800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
1 pathway
Crizotinib Drug Metabolism Action Pathway
Crizotinib Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureAngiopoietin-1 receptorQ02858Mus musculusPredicted (SEA)0.0778492
Hepatocyte growth factor receptor structureClick to view 3D structureHepatocyte growth factor receptorP08581HumansPredicted (SEA)0.0778492
ALK tyrosine kinase receptor structureClick to view 3D structureALK tyrosine kinase receptorQ9UM73HumansPredicted (SEA)0.155698
Tyrosine-protein kinase JAK2 structureClick to view 3D structureTyrosine-protein kinase JAK2O60674HumansPredicted (SEA)0.233548
Tyrosine-protein kinase receptor UFO structureClick to view 3D structureTyrosine-protein kinase receptor UFOP30530HumansPredicted (SEA)0.311397
Macrophage-stimulating protein receptor structureClick to view 3D structureMacrophage-stimulating protein receptorQ04912HumansPredicted (SEA)0.311397
Tyrosine-protein kinase ABL1 structureClick to view 3D structureTyrosine-protein kinase ABL1P00519HumansPredicted (SEA)1.94623
Ephrin type-A receptor 2 structureClick to view 3D structureEphrin type-A receptor 2P29317HumansPredicted (SEA)0.856341
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)2.56902
Mitogen-activated protein kinase kinase kinase kinase 3 structureClick to view 3D structureMitogen-activated protein kinase kinase kinase kinase 3Q8IVH8HumansPredicted (SEA)0.0778492
Fibroblast growth factor receptor 1 structureClick to view 3D structureFibroblast growth factor receptor 1P11362HumansPredicted (SEA)2.49118
Vascular endothelial growth factor receptor 1 structureClick to view 3D structureVascular endothelial growth factor receptor 1P17948HumansPredicted (SEA)1.32344
Proto-oncogene tyrosine-protein kinase receptor Ret structureClick to view 3D structureProto-oncogene tyrosine-protein kinase receptor RetP07949HumansPredicted (SEA)1.40129
Tyrosine-protein kinase receptor TYRO3 structureClick to view 3D structureTyrosine-protein kinase receptor TYRO3Q06418HumansPredicted (SEA)1.24559
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)3.26967
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)9.809
Platelet-derived growth factor receptor alpha structureClick to view 3D structurePlatelet-derived growth factor receptor alphaP16234HumansPredicted (SEA)2.80257
Mast/stem cell growth factor receptor Kit structureClick to view 3D structureMast/stem cell growth factor receptor KitP10721HumansPredicted (SEA)6.07224
Platelet-derived growth factor receptor beta structureClick to view 3D structurePlatelet-derived growth factor receptor betaP09619HumansPredicted (SEA)3.81461
Receptor-type tyrosine-protein kinase FLT3 structureClick to view 3D structureReceptor-type tyrosine-protein kinase FLT3P36888HumansPredicted (SEA)16.1926
Receptor tyrosine-protein kinase erbB-2 structureClick to view 3D structureReceptor tyrosine-protein kinase erbB-2P04626HumansPredicted (SEA)7.31783
Aurora kinase A structureClick to view 3D structureAurora kinase AO14965HumansPredicted (SEA)9.41976
3-phosphoinositide-dependent protein kinase 1 structureClick to view 3D structure3-phosphoinositide-dependent protein kinase 1O15530HumansPredicted (SEA)4.12601
Aurora kinase B structureClick to view 3D structureAurora kinase BQ96GD4HumansPredicted (SEA)11.5995
Leukocyte tyrosine kinase receptor structureClick to view 3D structureLeukocyte tyrosine kinase receptorP29376HumansPredicted (SEA)2.02408
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0250539
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID9772331
ChEBI ID77562
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References