B49

N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carbo xamide



Chemical Component Summary

NameN-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carbo xamide
SynonymsSUNITINIB
IdentifiersN-(2-diethylaminoethyl)-5-[(Z)-(5-fluoranyl-2-oxidanylidene-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide
FormulaC22 H27 F N4 O2
Molecular Weight398.474
TypeNON-POLYMER
Isomeric SMILESCCN(CC)CCNC(=O)c1c(c([nH]c1C)/C=C\2/c3cc(ccc3NC2=O)F)C
InChIInChI=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-
InChIKeyWINHZLLDWRZWRT-ATVHPVEESA-N

Chemical Details

Formal Charge0
Atom Count56
Chiral Atom Count0
Bond Count58
Aromatic Bond Count11

Drug Info: DrugBank

DrugBank IDDB01268 
NameSunitinib
Groups
  • approved
  • investigational
DescriptionSunitinib is a small-molecule multi-targeted receptor tyrosine kinase (RTK) inhibitor. On January 26, 2006, the agent was formally approved by the US FDA for the indications of treating renal cell carcinoma (RCC) and imatinib-resistant gastrointestinal stromal tumor (GIST). For these purposes, sunitinib is generally available as an orally administered formulation. Sunitinib inhibits cellular signaling by targeting multiple RTKs. These include all platelet-derived growth factor receptors (PDGF-R) and vascular endothelial growth factor receptors (VEGF-R). Sunitinib also inhibits KIT (CD117), the RTK that drives the majority of GISTs. In addition, sunitinib inhibits other RTKs including RET, CSF-1R, and flt3.
Synonyms
  • Sunitinibum
  • Sunitinib malate
  • Sunitinib
Brand Names
  • Sunitinib Accord
  • Teva-sunitinib
  • Sunitinib Malate
  • Sutent
  • Nat-sunitinib
IndicationSunitinib is indicated for the following conditions:[L4135] - Treatment of adult patients with gastrointestinal stromal tumor (GIST) following disease progression on (or intolerance to) [imatinib] mesylate - Treatment of adult patients with advanced renal cell carcinoma (RCC) - Adjuvant treatment of adult patients at high risk of recurrent RCC following nephrectomy - Treatment of progressive, well-differentiated pancreatic neuroendocrine tumors (pNET) in adult patients with unresectable locally advanced or metastatic disease
Categories
  • Angiogenesis Inhibitors
  • Angiogenesis Modulating Agents
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • BCRP/ABCG2 Inhibitors
ATC-CodeL01EX01
CAS number557795-19-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Platelet-derived growth factor receptor betaMRLPGAMPALALKGELLLLSLLLLLEPQISQGLVVTPPGPELVLNVSSTF...unknowninhibitor
Vascular endothelial growth factor receptor 1MVSYWDTGVLLCALLSCLLLTGSSSGSKLKDPELSLKGTQHIMQAGQTLH...unknowninhibitor
Mast/stem cell growth factor receptor KitMRGARGAWDFLCVLLLLLRVQTGSSQPSVSPGEPSPPSIHPGKSDLIVRV...unknowninhibitor
Vascular endothelial growth factor receptor 2MQSKVLLAVALWLCVETRAASVGLPSVSLDLPRLSIQKDILTIKANTTLQ...unknowninhibitor
Vascular endothelial growth factor receptor 3MQRGAALCLRLWLCLGLLDGLVSGYSMTPPTLNITEESHVIDTGDSLSIS...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 CHEMBL535
PubChem 5329102
ChEMBL CHEMBL535
ChEBI CHEBI:38940, CHEBI:91430
CCDC/CSD PICVUU01, PICVUU