Nabumetone

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Nabumetone
Nabumetone.svg
Systematic (IUPAC) name
4-(6-methoxy-2-naphthyl)-2-butanone
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a692022
Legal status
  • AU: S4 (Prescription only)
  • POM
Routes of
administration		 Oral
Pharmacokinetic data
Protein binding > 99% (active metabolite)
Metabolism Hepatic, to active metabolite 6-methoxy-2-naphthylacetic acid; 6-MNA
Biological half-life 23 hours (active metabolite)
Excretion Renal
Identifiers
CAS Number 42924-53-8 YesY
ATC code M01AX01 (WHO)
PubChem CID: 4409
IUPHAR/BPS 7245
DrugBank DB00461 YesY
ChemSpider 4256 YesY
UNII LW0TIW155Z YesY
KEGG D00425 YesY
ChEBI CHEBI:7443 N
ChEMBL CHEMBL1070 YesY
Chemical data
Formula C15H16O2
Molecular mass 228.29 g/mol
  • O=C(C)CCc1ccc2c(c1)ccc(OC)c2
  • InChI=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 YesY
  • Key:BLXXJMDCKKHMKV-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

Nabumetone is a non-steroidal anti-inflammatory drug[1] (NSAID), the only 1-naphthaleneacetic acid derivative. Nabumetone has been developed by Beecham. It is available under numerous brand names, such as Relafen, Relifex, and Gambaran.

Nabumetone is a nonacidic NSAID that is rapidly metabolized in the liver to a major active metabolite, 6-methoxy-2-naphthyl acetic acid. As found with previous NSAIDs, nabumetone's active metabolite inhibits the cyclooxygenase enzyme and preferentially blocks COX-2 activity (which is indirectly responsible for the production of inflammation and pain during arthritis). The active metabolite of nabumetone is felt to be the compound primarily responsible for therapeutic effect. Comparatively, the parent drug is a poor inhibitor of COX-2 byproducts, particularly prostaglandins. It may be less nephrotoxic than indomethacin.[2]

Nabumetone has little effect on renal prostaglandin secretion and less of an association with heart failure than other traditional drugs of the class.[3] Effects of nabumetone on blood pressure control in hypertensive patients on ACE inhibitors is also good—equivalent to paracetamol.[4] As of 2015 the cost for a typical month of medication in the United States is 25 to 50 USD.[5]

Medical uses

It is effects of enzymes that cause pain and inflammation.[citation needed]

Side effects

It has been shown to have a slightly lower risk of gastrointestinal side effects than most other non-selective NSAIDs since it is a non-acidic prodrug which is then metabolized to its active 6MNA (6-methoxy-2-naphthylacetic acid) form.[citation needed]

Assay of nabumetone

There are few papers published reporting analytical methods[6] for nabumetone.[7] Two of them employed HPLC with UV-detection.[8][9] One HPLC method using direct injection on restricted access media columns.[10] Flow injection analysis (FIA) with UV-detection was also reported for the determination of nabumetone in pharmaceutical preparations.[11] Methods using HPLC with fluorescence detection [12][13][14][15] were reported. M. Nobilis et al. carried out biotransformation and disposition studies in humans and minipigs using HPLC with UV, fluorescence and mass spectrometric detection. The interactions with gamma-cyclodextrin were also studied by fluorescence measurements. Assay methods employed HPLC using UV detection,[7] photodiode array (PDA) detector[16][17] and mass spectrometric detection for the determination of nabumetone and its metabolites. Murillo Pulgarín et al.[18][19][20] reported three analytical methods using different techniques along with phosphorescence. Liquid chromatography methods using different techniques of mass spectrometry were also reported.[21][22][23] The electrochemical behavior of nabumetone by a voltammetric technique [24] and a novel colorimetric method based on chemical derivatization [25] were also published. P. K. Sahu et al.[26] has reported a HPLC method for simultaneous estimation of Nabumetone and Paracetamol in combined dosage form.

References

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