XIN

methyl (3Z)-3-{[(4-{methyl[(4-methylpiperazin-1-yl)acetyl]amino}phenyl)amino](phenyl)methylidene}-2-oxo-2,3-dihydro-1H-indole-6-carboxylate

Created: 2008-02-20
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count73
Chiral Atom Count0
Bond Count77
Aromatic Bond Count18
2D diagram of XIN
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Chemical Component Summary

Namemethyl (3Z)-3-{[(4-{methyl[(4-methylpiperazin-1-yl)acetyl]amino}phenyl)amino](phenyl)methylidene}-2-oxo-2,3-dihydro-1H-indole-6-carboxylate
Systematic Name (OpenEye OEToolkits)methyl (3Z)-3-[[[4-[methyl-[2-(4-methylpiperazin-1-yl)ethanoyl]amino]phenyl]amino]-phenyl-methylidene]-2-oxo-1H-indole-6-carboxylate
FormulaC31 H33 N5 O4
Molecular Weight539.625
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(OC)c1cc2c(cc1)/C(C(=O)N2)=C(\c3ccccc3)Nc4ccc(cc4)N(C(=O)CN5CCN(C)CC5)C
SMILESCACTVS3.341COC(=O)c1ccc2c(NC(=O)C2=C(Nc3ccc(cc3)N(C)C(=O)CN4CCN(C)CC4)c5ccccc5)c1
SMILESOpenEye OEToolkits1.5.0CN1CCN(CC1)CC(=O)N(C)c2ccc(cc2)NC(=C3c4ccc(cc4NC3=O)C(=O)OC)c5ccccc5
Canonical SMILESCACTVS3.341 COC(=O)c1ccc\2c(NC(=O)C\2=C(Nc3ccc(cc3)N(C)C(=O)CN4CCN(C)CC4)/c5ccccc5)c1
Canonical SMILESOpenEye OEToolkits1.5.0 CN1CCN(CC1)CC(=O)N(C)c2ccc(cc2)N/C(=C\3/c4ccc(cc4NC3=O)C(=O)OC)/c5ccccc5
InChIInChI1.03 InChI=1S/C31H33N5O4/c1-34-15-17-36(18-16-34)20-27(37)35(2)24-12-10-23(11-13-24)32-29(21-7-5-4-6-8-21)28-25-14-9-22(31(39)40-3)19-26(25)33-30(28)38/h4-14,19,32H,15-18,20H2,1-3H3,(H,33,38)/b29-28-
InChIKeyInChI1.03 XZXHXSATPCNXJR-ZIADKAODSA-N

Drug Info: DrugBank

DrugBank IDDB09079 
NameNintedanib
Groups approved
DescriptionNintedanib is a small molecule kinase inhibitor used in the treatment of pulmonary fibrosis, systemic sclerosis-associated interstitial lung disease, and non-small cell lung cancer (NSCLC).[L8453,L8459] It was first approved for use in the United States in 2014.[L8453] Within the spectrum of idiopathic pulmonary fibrosis treatment options, nintedanib is currently one of only two disease-modifying therapies available and indicated for the condition (the other being [Pirfenidone]) and as such is used as a first-line treatment following diagnosis to slow down the progressive loss of lung function.[A185237] As a chemotherapeutic agent for NSCLC, nintedanib, in combination with [Docetaxel], is reserved for patients who have tried and failed first-line chemotherapeutic options.[L8459]
Synonyms
  • Nintedanib
  • methyl (3Z)-3-[(4-{methyl[(4-methylpiperazin-1-yl)acetyl]amino}anilino)(phenyl)methylidene]-2-oxo-2,3-dihydro-1H-indole-6-carboxylate
  • Nintedanib esylate
Brand Names
  • Jamp Nintedanib
  • Vargatef
  • Ofev
  • Auro-nintedanib
IndicationNintedanib is indicated for the treatment of idiopathic pulmonary fibrosis (IPF)[L8453] and to slow declining pulmonary function in patients with systemic sclerosis-associated interstitial lung disease.[L8462] It is also indicated for the treatment of chronic fibrosing interstitial lung diseases with a progressive phenotype.[L8462] In the EU, under the brand name Vargatef, nintedanib is indicated in combination with docetaxel for the treatment of adult patients with metastatic, locally advanced, or locally recurrent non-small cell lung cancer of adenocarcinoma histology who have already tried first-line therapy.[L8459]
Categories
  • Antifibrotic Agents
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • Cytochrome P-450 CYP3A Substrates
  • Cytochrome P-450 CYP3A4 Substrates
ATC-CodeL01EX09
CAS number656247-17-5

Drug Targets

NameTarget SequencePharmacological ActionActions
Vascular endothelial growth factor receptor 1MVSYWDTGVLLCALLSCLLLTGSSSGSKLKDPELSLKGTQHIMQAGQTLH...unknowninhibitor
Vascular endothelial growth factor receptor 2MQSKVLLAVALWLCVETRAASVGLPSVSLDLPRLSIQKDILTIKANTTLQ...unknowninhibitor
Vascular endothelial growth factor receptor 3MQRGAALCLRLWLCLGLLDGLVSGYSMTPPTLNITEESHVIDTGDSLSIS...unknowninhibitor
Platelet-derived growth factor receptor alphaMGTSHPAFLVLGCLLTGLSLILCQLSLPSILPNENEKVVQLNSSFSLRCF...unknowninhibitor
Platelet-derived growth factor receptor betaMRLPGAMPALALKGELLLLSLLLLLEPQISQGLVVTPPGPELVLNVSSTF...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
PubChem 9809715