Chemical Component Summary

Name4-NITRO-2-PHENOXYMETHANESULFONANILIDE
SynonymsNIMESULIDE
IdentifiersN-(4-nitro-2-phenoxy-phenyl)methanesulfonamide
FormulaC13 H12 N2 O5 S
Molecular Weight308.31
TypeNON-POLYMER
Isomeric SMILESCS(=O)(=O)Nc1ccc(cc1Oc2ccccc2)[N+](=O)[O-]
InChIInChI=1S/C13H12N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h2-9,14H,1H3
InChIKeyHYWYRSMBCFDLJT-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count33
Chiral Atom Count0
Bond Count34
Aromatic Bond Count12

Drug Info: DrugBank

DrugBank IDDB04743 
NameNimesulide
Groups
  • approved
  • investigational
  • withdrawn
DescriptionNimesulide is a relatively COX-2 selective, non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Its approved indications are the treatment of acute pain, the symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults above 12 years old. Due to concerns about the risk of hepatotoxicity, nimesulide has been withdrawn from market in many countries.
Synonyms
  • Nimesulide
  • Nimesulidum
  • Nimesulida
IndicationFor the treatment of acute pain, the symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults above 12 years old.
Categories
  • Agents causing hyperkalemia
  • Agents that produce hypertension
  • Amides
  • Analgesics
  • Analgesics, Non-Narcotic
ATC-Code
  • M01AX17
  • M02AA26
CAS number51803-78-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Prostaglandin G/H synthase 2MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...unknowninhibitor
Group IIE secretory phospholipase A2MKSPHVLVFLCLLVALVTGNLVQFGVMIEKMTGKSALQYNDYGCYCGIGG...unknown
LactotransferrinMKLVFLVLLFLGALGLCLAGRRRSVQWCAVSQPEATKCFQWQRNMRKVRG...unknown
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
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 CHEMBL56367
PubChem 4495
ChEMBL CHEMBL56367
ChEBI CHEBI:44445
CCDC/CSD WINWUL02, WINWUL, WINWUL03, WINWUL01, LAKMET, LAKLOC, LAKMAP, LAKLUI