Chemical Component Summary

Namenabumetone
Synonyms4-(6-methoxynaphthalen-2-yl)butan-2-one
Identifiers4-(6-methoxynaphthalen-2-yl)butan-2-one
FormulaC15 H16 O2
Molecular Weight228.286
TypeNON-POLYMER
Isomeric SMILESCC(=O)CCc1ccc2cc(ccc2c1)OC
InChIInChI=1S/C15H16O2/c1-11(16)3-4-12-5-6-14-10-15(17-2)8-7-13(14)9-12/h5-10H,3-4H2,1-2H3
InChIKeyBLXXJMDCKKHMKV-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count33
Chiral Atom Count0
Bond Count34
Aromatic Bond Count11

Drug Info: DrugBank

DrugBank IDDB00461 
NameNabumetone
Groups approved
DescriptionNabumetone was originally developed as a non-acidic non-steroidal anti-inflammatory drug (NSAID).[label] It was thought to avoid trapping of the drug in the stomach by making it unable to dissociate into ions which was believed to reduce GI toxicity by limiting local action.[A179077] While slightly reduced, possibly due to a degree of cyclooxygenase-2 selectivity (COX-2), nabumetone still produces significant adverse effects in the GI tract.[label,A178903] The molecule itself is a pro-drug with its 6-methoxy-2-naphthylacetic acid (6-MNA) metabolite acting as a potent COX inhibitor similar in structure to [naproxen]. Nabumetone was developed by Smithkline Beecham under the trade name Relafen and first received FDA approval in December, 1991.[L6568]
Synonyms
  • 4-(6-Methoxy-2-naphthyl)-2-butanone
  • Nabumetonum
  • Nabumeton
  • 4-(6-Methoxy-2-naphthalenyl)-2-butanone
  • Nabumétone
Brand Names
  • Nabumetone 1000 mg
  • NuDroxiPAK N-500
  • Mylan-nabumetone
  • Relafen Tablets 750mg
  • Nabumetone
Indication**Indicated** for:[label] 1) Symptomatic relief in rheumatoid arthritis. 2) Symptomatic relief in osteoarthritis.
Categories
  • Agents causing hyperkalemia
  • Agents that produce hypertension
  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory Agents
ATC-CodeM01AX01
CAS number42924-53-8

Drug Targets

NameTarget SequencePharmacological ActionActions
Prostaglandin G/H synthase 2MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...unknowninhibitor
Prostaglandin G/H synthase 1MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...unknowninhibitor
MyeloperoxidaseMGVPFFSSLRCMVDLGPCWAGGLTAEMKLLLALAGLLAILATPQPSEGAA...unknowninhibitor
Cytochrome P450 1A2MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...unknownsubstrate
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate
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 CHEMBL1070
PubChem 4409
ChEMBL CHEMBL1070
ChEBI CHEBI:7443
CCDC/CSD XOCXUI01, XOCXUI02, XOCXUI03, XOCXUI, XOCXUI04
COD 4505829, 4505830