Sunitinib (CED0001500)

Record Information
Version1.0
Creation Date2016-05-25 18:26:27 UTC
Update Date2026-08-21 22:32:34 UTC
Accession NumberCHEM022273
Identification
Common NameSunitinib
ClassSmall Molecule
Description
Sunitinib is an organic compound with the formula C22H27FN4O2 and an average molecular weight of 398.47 g/mol. Sunitinib belongs to the indolines, a subclass of indoles and derivatives within the organic compounds. This compound is recorded as being found in or released from seven sources, including antineoplastic agents within healthcare, pharmaceuticals and veterinary products; preparation of malt within food, food processing and cookware; non electric simulated smoking devices and pipe accessories within household cleaning and consumer products; and antennas, electric hearing aids and line transmission systems within electrical and electronic equipment. The recorded exposure route for this substance is oral. At the molecular level, sunitinib acts as an inhibitor for nine protein targets, including vascular endothelial growth factor receptor 1 (FLT1), vascular endothelial growth factor receptor 2 (KDR), vascular endothelial growth factor receptor 3 (FLT4), and platelet-derived growth factor receptor beta (PDGFRB), as well as five other proteins. In clinical applications, sunitinib is used as a treatment for cancer (PMC12022389, PMC12663558), renal cell carcinoma (PMC10173257), and diabetic retinopathy (PMC4949763). Additionally, it has a therapeutic effect on angiosarcoma (PMC5102718). The use of this compound is associated with rash (PMC13084601).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SU-11248ChEBI
SunitinibumChEBI
SutentChEBI
SU11248HMDB
Sunitinib malateHMDB
5-(5-Fluoro-2-oxo-1,2-dihydroindolylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amideHMDB
Chemical FormulaC22H27FN4O2
Average Molecular Mass398.474 g/mol
Monoisotopic Mass398.212 g/mol
CAS Registry Number557795-19-4
IUPAC NameN-[2-(diethylamino)ethyl]-5-{[(3Z)-5-fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene]methyl}-2,4-dimethyl-1H-pyrrole-3-carboxamide
Traditional Namesunitinib
SMILESCCN(CC)CCNC(=O)C1=C(C)NC(\C=C2/C(=O)NC3=C2C=C(F)C=C3)=C1C
InChI IdentifierInChI=1S/C22H27FN4O2/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28)/b17-12-
InChI KeyWINHZLLDWRZWRT-ATVHPVEESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolines
Direct ParentIndolines
Alternative Parents
Substituents
  • Dihydroindole
  • Pyrrole-3-carboxamide
  • Pyrrole-3-carboxylic acid or derivatives
  • Aryl fluoride
  • Aryl halide
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary amine
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Tertiary aliphatic amine
  • Carboxamide group
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Amine
  • Organofluoride
  • Organohalogen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • 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 Solubility0.031 g/LALOGPS
logP3.24ALOGPS
logP2.93ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)11.46ChemAxon
pKa (Strongest Basic)9.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.23 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity116.27 m³·mol⁻¹ChemAxon
Polarizability44.32 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001r-9043000000-f9288d8cb7c447b10d86Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0419000000-d91569989d4c1e438a58Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-1039-4964000000-32cdbd9b3679f4b806d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9740000000-14530852543a6132d98bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0019000000-716107e6148bcb3af14cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052b-5398000000-e20fbe1cd3f11ad37acbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9230000000-0d8caf257003c837c3d6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0009000000-c7521df282758983a81bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-003r-0197000000-fc31f5a3f60673e3fb48Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0293000000-c9aae10759016725c932Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0009000000-f6f1dd2f48935333770cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-2049000000-fe9e71e910a9eddb2023Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052g-6194000000-ce0d447fabdb293e1813Not 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
1659.0Log mg/kg[930:3000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
canceris_treatment_forNot AvailablePMC12022389 , PMC12663558
angiosarcomahas_therapeutic_effect_onNot AvailablePMC5102718
rashassociated_withNot AvailablePMC13084601
renal cell carcinomais_treatment_forNot AvailablePMC10173257
diabetic retinopathyis_treatment_forNot AvailablePMC4949763
gastrointestinal stromal tumoris_treatment_forNot AvailablePMC3756423
mucositisassociated_withNot AvailablePMC10169589
cholangiocarcinomais_treatment_forNot AvailablePMC6394015
chronic eosinophilic leukemiais_treatment_forNot AvailablePMC10580003
Exposure Sources
Source IDSourceSectorReference
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
Pathways
2 pathways
Sunitinib Action Pathway
Sunitinib Action Pathway
Sunitinib Drug Metabolism Action Pathway
Sunitinib Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
5'-AMP-activated protein kinase catalytic subunit alpha-1 structureClick to view 3D structure5'-AMP-activated protein kinase catalytic subunit alpha-1Q13131HumansPredicted (SEA)0.155698
Fibroblast growth factor receptor 1 structureClick to view 3D structureFibroblast growth factor receptor 1P11362HumansPredicted (SEA)0.155698
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)0.0778492
Macrophage colony-stimulating factor 1 receptor structureClick to view 3D structureMacrophage colony-stimulating factor 1 receptorP07333HumansPredicted (SEA)0.155698
Mast/stem cell growth factor receptor Kit structureClick to view 3D structureMast/stem cell growth factor receptor KitP10721HumansPredicted (SEA)0.155698
5'-AMP-activated protein kinase catalytic subunit alpha-2 structureClick to view 3D structure5'-AMP-activated protein kinase catalytic subunit alpha-2P54646HumansPredicted (SEA)0.0778492
Receptor-type tyrosine-protein kinase FLT3 structureClick to view 3D structureReceptor-type tyrosine-protein kinase FLT3P36888HumansPredicted (SEA)0.311397
Maternal embryonic leucine zipper kinase structureClick to view 3D structureMaternal embryonic leucine zipper kinaseQ14680HumansPredicted (SEA)0.544945
Serine/threonine-protein kinase Nek2 structureClick to view 3D structureSerine/threonine-protein kinase Nek2P51955HumansPredicted (SEA)0.389246
Platelet-derived growth factor receptor alpha structureClick to view 3D structurePlatelet-derived growth factor receptor alphaP16234HumansPredicted (SEA)0.233548
Vascular endothelial growth factor receptor 1 structureClick to view 3D structureVascular endothelial growth factor receptor 1P17948HumansPredicted (SEA)0.856341
Proto-oncogene tyrosine-protein kinase receptor Ret structureClick to view 3D structureProto-oncogene tyrosine-protein kinase receptor RetP07949HumansPredicted (SEA)0.544945
Vascular endothelial growth factor receptor 3 structureClick to view 3D structureVascular endothelial growth factor receptor 3P35916HumansPredicted (SEA)0.311397
Serine/threonine-protein kinase tousled-like 2 structureClick to view 3D structureSerine/threonine-protein kinase tousled-like 2Q86UE8HumansPredicted (SEA)0.0778492
ALK tyrosine kinase receptor structureClick to view 3D structureALK tyrosine kinase receptorQ9UM73HumansPredicted (SEA)1.32344
Tyrosine-protein kinase Lck structureClick to view 3D structureTyrosine-protein kinase LckP06239HumansPredicted (SEA)3.26967
Focal adhesion kinase 1 structureClick to view 3D structureFocal adhesion kinase 1Q05397HumansPredicted (SEA)1.63483
Tyrosine-protein kinase ABL1 structureClick to view 3D structureTyrosine-protein kinase ABL1P00519HumansPredicted (SEA)2.72472
Tyrosine-protein kinase Fyn structureClick to view 3D structureTyrosine-protein kinase FynP06241HumansPredicted (SEA)2.33548
Serine/threonine-protein kinase Chk1 structureClick to view 3D structureSerine/threonine-protein kinase Chk1O14757HumansPredicted (SEA)1.16774
Phosphorylase b kinase gamma catalytic chain, liver/testis isoform structureClick to view 3D structurePhosphorylase b kinase gamma catalytic chain, liver/testis isoformP15735HumansPredicted (SEA)0.778492
Fibroblast growth factor receptor 3 structureClick to view 3D structureFibroblast growth factor receptor 3P22607HumansPredicted (SEA)1.40129
Tyrosine-protein kinase receptor UFO structureClick to view 3D structureTyrosine-protein kinase receptor UFOP30530HumansPredicted (SEA)0.934191
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)0.0778492
Platelet-derived growth factor receptor beta structureClick to view 3D structurePlatelet-derived growth factor receptor betaP09619HumansPredicted (SEA)0.0778492
Concentrations
Not Available
External Links
DrugBank IDDB01268
HMDB IDHMDB0015397
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDB49
Wikipedia LinkSunitinib
Chemspider ID4486264
ChEBI ID38940
PubChem Compound ID5329102
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Demetri GD, van Oosterom AT, Garrett CR, Blackstein ME, Shah MH, Verweij J, McArthur G, Judson IR, Heinrich MC, Morgan JA, Desai J, Fletcher CD, George S, Bello CL, Huang X, Baum CM, Casali PG: Efficacy and safety of sunitinib in patients with advanced gastrointestinal stromal tumour after failure of imatinib: a randomised controlled trial. Lancet. 2006 Oct 14;368(9544):1329-38.
2. Motzer RJ, Hutson TE, Tomczak P, Michaelson MD, Bukowski RM, Rixe O, Oudard S, Negrier S, Szczylik C, Kim ST, Chen I, Bycott PW, Baum CM, Figlin RA: Sunitinib versus interferon alfa in metastatic renal-cell carcinoma. N Engl J Med. 2007 Jan 11;356(2):115-24.
3. FDA label
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12531805
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16845442
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16916320
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=17327610
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=17962201
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=18971320
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=19830602
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=20406969
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21792888
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24188025
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24393200
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24402960
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24403097
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=24521256