Pazopanib (CED0002505)

Record Information
Version1.0
Creation Date2016-05-22 06:39:23 UTC
Update Date2026-08-21 18:55:53 UTC
Accession NumberCHEM019958
Identification
Common NamePazopanib
ClassSmall Molecule
Description
Pazopanib is an organic compound with the chemical formula C21H23N7O2S and an average molecular weight of 437.52 g/mol. Pazopanib belongs to the amines, a subclass of organonitrogen compounds within the organic compounds. This compound is recorded as being found in or released from three sources: electrical and electronic equipment, specifically antennas and electric hearing aids, as well as healthcare, pharmaceuticals, and veterinary products, where it is used as an antineoplastic agent. The recorded route of exposure for this substance is oral. In terms of biological activity, pazopanib acts on ten recorded protein targets. It functions as an inhibitor of Vascular endothelial growth factor receptor 1 (FLT1), Vascular endothelial growth factor receptor 2 (KDR), and Vascular endothelial growth factor receptor 3 (FLT4). Additionally, it inhibits Platelet-derived growth factor receptor alpha (PDGFRA) and six other proteins.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GW 78603ChEBI
GW786034ChEBI
PazopanibumChEBI
VotrientMeSH
Chemical FormulaC21H23N7O2S
Average Molecular Mass437.518 g/mol
Monoisotopic Mass437.163 g/mol
CAS Registry Number444731-52-6
IUPAC Name5-({4-[(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]pyrimidin-2-yl}amino)-2-methylbenzene-1-sulfonamide
Traditional Namepazopanib
SMILESCN(C1=CC2=NN(C)C(C)=C2C=C1)C1=CC=NC(NC2=CC=C(C)C(=C2)S(N)(=O)=O)=N1
InChI IdentifierInChI=1S/C21H23N7O2S/c1-13-5-6-15(11-19(13)31(22,29)30)24-21-23-10-9-20(25-21)27(3)16-7-8-17-14(2)28(4)26-18(17)12-16/h5-12H,1-4H3,(H2,22,29,30)(H,23,24,25)
InChI KeyCUIHSIWYWATEQL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAlkyldiarylamines
Alternative Parents
Substituents
  • Alkyldiarylamine
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Benzopyrazole
  • Indazole
  • Aniline or substituted anilines
  • Aminopyrimidine
  • Toluene
  • Monocyclic benzene moiety
  • Pyrimidine
  • Organosulfonic acid amide
  • Imidolactam
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • Pyrazole
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.043 g/LALOGPS
logP3.59ALOGPS
logP3.55ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)10.41ChemAxon
pKa (Strongest Basic)5.07ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.03 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity132.18 m³·mol⁻¹ChemAxon
Polarizability45.41 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-05fr-0902400000-3fb1fcfef2c003c0c9f9Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-0118900000-097bcfa914e959e3d51aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0910000000-fd84ad14c383d8fa623fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0001900000-601cc6acb40869cc82cdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0427900000-a50efbdd2b0e187398b9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-1943000000-f5acfb37eb7f20e99c33Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0000900000-fb6bc5d28ebdaa8645d3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-2342900000-92122fcd8c8d3adbd58aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9320000000-350f27636b7d840c92c6Not 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
2602.0Log mg/kg[1500:4600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
Pathways
2 pathways
Pazopanib Action Pathway
Pazopanib Action Pathway
Pazopanib Drug Metabolism Action Pathway
Pazopanib Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)3.34752
Vascular endothelial growth factor receptor 1 structureClick to view 3D structureVascular endothelial growth factor receptor 1P17948HumansPredicted (SEA)2.56902
Vascular endothelial growth factor receptor 3 structureClick to view 3D structureVascular endothelial growth factor receptor 3P35916HumansPredicted (SEA)3.11397
Macrophage colony-stimulating factor 1 receptor structureClick to view 3D structureMacrophage colony-stimulating factor 1 receptorP07333HumansPredicted (SEA)6.77288
Fibroblast growth factor receptor 1 structureClick to view 3D structureFibroblast growth factor receptor 1P11362HumansPredicted (SEA)19.3066
Platelet-derived growth factor receptor beta structureClick to view 3D structurePlatelet-derived growth factor receptor betaP09619HumansPredicted (SEA)17.7496
Mast/stem cell growth factor receptor Kit structureClick to view 3D structureMast/stem cell growth factor receptor KitP10721HumansPredicted (SEA)30.8283
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)19.5402
Click to view 3D structureSerine/threonine-protein kinase TAO2Q9UL54HumansPredicted (SEA)2.25763
Serine/threonine-protein kinase 16 structureClick to view 3D structureSerine/threonine-protein kinase 16O75716HumansPredicted (SEA)4.98235
Mitogen-activated protein kinase kinase kinase 11 structureClick to view 3D structureMitogen-activated protein kinase kinase kinase 11Q16584HumansPredicted (SEA)7.94062
Ephrin type-B receptor 4 structureClick to view 3D structureEphrin type-B receptor 4P54760HumansPredicted (SEA)24.0554
Receptor-interacting serine/threonine-protein kinase 1 structureClick to view 3D structureReceptor-interacting serine/threonine-protein kinase 1Q13546HumansPredicted (SEA)5.68299
Receptor-interacting serine/threonine-protein kinase 3 structureClick to view 3D structureReceptor-interacting serine/threonine-protein kinase 3Q9Y572HumansPredicted (SEA)8.17417
Tyrosine-protein kinase SYK structureClick to view 3D structureTyrosine-protein kinase SYKP43405HumansPredicted (SEA)56.2071
Tyrosine-protein kinase Lyn structureClick to view 3D structureTyrosine-protein kinase LynP07948HumansPredicted (SEA)73.0226
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)84.155
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)79.2505
Tyrosine-protein kinase TXK structureClick to view 3D structureTyrosine-protein kinase TXKP42681HumansPredicted (SEA)25.301
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)37.2898
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)133.122
Aurora kinase B structureClick to view 3D structureAurora kinase BQ96GD4HumansPredicted (SEA)101.515
Aurora kinase A structureClick to view 3D structureAurora kinase AO14965HumansPredicted (SEA)110.935
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)164.573
Tyrosine-protein kinase CSK structureClick to view 3D structureTyrosine-protein kinase CSKP41240HumansPredicted (SEA)33.0081
Concentrations
Not Available
External Links
DrugBank IDDB06589
HMDB IDHMDB0256144
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPazopanib
Chemspider ID8289501
ChEBI ID71219
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21394443
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21766486
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21811833
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22112314
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22190407
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22233389
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22341567
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22359392
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22595799
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22679111
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22688250
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22716487
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22733110
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22733795
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22759480
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22766517
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22830347
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22861374
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=22917595
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=22984765
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23054212
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23064954
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=23072642
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=23088634
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=23135778