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

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is present as a standalone ligand in 14 entries

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Chemical Component Summary
Name	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
Synonyms	SUNITINIB
Identifiers	N-(2-diethylaminoethyl)-5-[(Z)-(5-fluoranyl-2-oxidanylidene-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide
Formula	C₂₂ H₂₇ F N₄ O₂
Molecular Weight	398.474
Type	NON-POLYMER
Isomeric SMILES	CCN(CC)CCNC(=O)c1c(c([nH]c1C)/C=C\2/c3cc(ccc3NC2=O)F)C
InChI	InChI=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-
InChIKey	WINHZLLDWRZWRT-ATVHPVEESA-N

Chemical Details
Formal Charge	0
Atom Count	56
Chiral Atom Count	0
Bond Count	58
Aromatic Bond Count	11

Drug Info: DrugBank

DrugBank ID	DB01268
Name	Sunitinib
Groups	approved investigational
Description	Sunitinib 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	Sunitinib malate Sunitinib Sunitinibum
Brand Names	Taro-sunitinib Sunitinib Accord Auro-sunitinib Sunitinib malate Nat-sunitinib Teva-sunitinib Sandoz Sunitinib Sutent Sunitinib Malate
Indication	Sunitinib 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 Blood Glucose Lowering Agents Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A5 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 CYP3A7 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Enzyme Inhibitors Growth Inhibitors Growth Substances Hepatotoxic Agents Heterocyclic Compounds, Fused-Ring Hypoglycemia-Associated Agents Immunosuppressive Agents Indoles Kinase Inhibitor Narrow Therapeutic Index Drugs P-glycoprotein inhibitors P-glycoprotein substrates Potential QTc-Prolonging Agents Protein Kinase Inhibitors QTc Prolonging Agents Tyrosine Kinase Inhibitors
ATC-Code	L01EX01
CAS number	557795-19-4

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Platelet-derived growth factor receptor beta	MRLPGAMPALALKGELLLLSLLLLLEPQISQGLVVTPPGPELVLNVSSTF...	unknown	inhibitor
Vascular endothelial growth factor receptor 1	MVSYWDTGVLLCALLSCLLLTGSSSGSKLKDPELSLKGTQHIMQAGQTLH...	unknown	inhibitor
Mast/stem cell growth factor receptor Kit	MRGARGAWDFLCVLLLLLRVQTGSSQPSVSPGEPSPPSIHPGKSDLIVRV...	unknown	inhibitor
Vascular endothelial growth factor receptor 2	MQSKVLLAVALWLCVETRAASVGLPSVSLDLPRLSIQKDILTIKANTTLQ...	unknown	inhibitor
Vascular endothelial growth factor receptor 3	MQRGAALCLRLWLCLGLLDGLVSGYSMTPPTLNITEESHVIDTGDSLSIS...	unknown	inhibitor
Receptor-type tyrosine-protein kinase FLT3	MPALARDGGQLPLLVVFSAMIFGTITNQDLPVIKCVLINHKNNDSSVGKS...	unknown	inhibitor
Macrophage colony-stimulating factor 1 receptor	MGPGVLLLLLVATAWHGQGIPVIEPSVPELVVKPGATVTLRCVGNGSVEW...	unknown	inhibitor
Platelet-derived growth factor receptor alpha	MGTSHPAFLVLGCLLTGLSLILCQLSLPSILPNENEKVVQLNSSFSLRCF...	unknown	inhibitor
Hepatocyte growth factor receptor	MKAPAVLAPGILVLLFTLVQRSNGECKEALAKSEMNVNMKYQLPNFTAET...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate
Cytochrome P450 3A7	MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...	unknown	substrate
Multidrug resistance-associated protein 4	MLPVYQEVKPNPLQDANLCSRVFFWWLNPLFKIGHKRRLEEDDMYSVLPE...	unknown	inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inhibitor
Canalicular multispecific organic anion transporter 1	MLEKFCNSTFWNSSFLDSPEADLPLCFEQTVLVWIPLGYLWLLAPWQLLH...	unknown	inhibitor
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	inhibitor
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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