BAX

4-{4-[({[4-CHLORO-3-(TRIFLUOROMETHYL)PHENYL]AMINO}CARBONYL)AMINO]PHENOXY}-N-METHYLPYRIDINE-2-CARBOXAMIDE

Created: 2004-02-05
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count48
Chiral Atom Count0
Bond Count50
Aromatic Bond Count18
2D diagram of BAX
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Chemical Component Summary

Name4-{4-[({[4-CHLORO-3-(TRIFLUOROMETHYL)PHENYL]AMINO}CARBONYL)AMINO]PHENOXY}-N-METHYLPYRIDINE-2-CARBOXAMIDE
SynonymsSorafenib
Systematic Name (OpenEye OEToolkits)4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide
FormulaC21 H16 Cl F3 N4 O3
Molecular Weight464.825
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(c3nccc(Oc2ccc(NC(=O)Nc1ccc(Cl)c(c1)C(F)(F)F)cc2)c3)NC
SMILESCACTVS3.341CNC(=O)c1cc(Oc2ccc(NC(=O)Nc3ccc(Cl)c(c3)C(F)(F)F)cc2)ccn1
SMILESOpenEye OEToolkits1.5.0CNC(=O)c1cc(ccn1)Oc2ccc(cc2)NC(=O)Nc3ccc(c(c3)C(F)(F)F)Cl
Canonical SMILESCACTVS3.341 CNC(=O)c1cc(Oc2ccc(NC(=O)Nc3ccc(Cl)c(c3)C(F)(F)F)cc2)ccn1
Canonical SMILESOpenEye OEToolkits1.5.0 CNC(=O)c1cc(ccn1)Oc2ccc(cc2)NC(=O)Nc3ccc(c(c3)C(F)(F)F)Cl
InChIInChI1.03 InChI=1S/C21H16ClF3N4O3/c1-26-19(30)18-11-15(8-9-27-18)32-14-5-2-12(3-6-14)28-20(31)29-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,28,29,31)
InChIKeyInChI1.03 MLDQJTXFUGDVEO-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00398 
NameSorafenib
Groups
  • approved
  • investigational
DescriptionSorafenib is a bi-aryl urea and an oral multikinase inhibitor. It targets cell surface tyrosine kinase receptors and downstream intracellular kinases that are implicated in tumour cell proliferation and tumour angiogenesis.[A255852] First approved by the FDA and European Commission in 2007 for the treatment of hepatocellular carcinoma, sorafenib is also indicated to treat renal carcinoma and differentiated thyroid carcinoma.[A14794]
Synonyms
  • N-(4-Chloro-3-(trifluoromethyl)phenyl)-N'-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl)urea
  • Sorafenibum
  • Sorafenib
  • Sorafenib tosylate
  • 4-(4-((((4-Chloro-3-(trifluoromethyl)phenyl)amino)carbonyl)amino)phenoxy)-N-methyl-2-pyridinecarboxamide
Brand Names
  • Sorafenib
  • Nexavar
  • Apo-sorafenib
  • Sorafenib Tosylate
IndicationSorafenib is indicated for the treatment of unresectable hepatocellular carcinoma and advanced renal cell carcinoma.[L9341,L44577] In the US, it is also indicated for the treatment of patients with locally recurrent or metastatic, progressive, differentiated thyroid carcinoma that is refractory to radioactive iodine treatment.[L9341]
Categories
  • Amides
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • BCRP/ABCG2 Inhibitors
  • BCRP/ABCG2 Substrates
ATC-CodeL01EX02
CAS number284461-73-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Serine/threonine-protein kinase B-rafMAALSGGGGGGAEPGQALFNGDMEPEAGAGAGAAASSAADPAIPEEVWNI...unknowninhibitor
RAF proto-oncogene serine/threonine-protein kinaseMEHIQGAWKTISNGFGFKDAVFDGSSCISPTIVQQFGYQRRASDDGKLTD...unknowninhibitor
Vascular endothelial growth factor receptor 3MQRGAALCLRLWLCLGLLDGLVSGYSMTPPTLNITEESHVIDTGDSLSIS...unknowninhibitor
Vascular endothelial growth factor receptor 2MQSKVLLAVALWLCVETRAASVGLPSVSLDLPRLSIQKDILTIKANTTLQ...unknowninhibitor
Vascular endothelial growth factor receptor 1MVSYWDTGVLLCALLSCLLLTGSSSGSKLKDPELSLKGTQHIMQAGQTLH...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 CHEMBL1336
PubChem 216239
ChEMBL CHEMBL1336
ChEBI CHEBI:50924
CCDC/CSD AKENOU, HOLKIF, HOLKEB, HOLKAX, HAHDED
COD 2017920