Nabumetone

Nabumetone
Clinical data
Trade names	Relafen
AHFS/Drugs.com	Monograph
MedlinePlus	a692022
License data	US DailyMed: Nabumetone;
Routes of; administration	By mouth
ATC code	M01AX01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Protein binding	> 99% (active metabolite)
Metabolism	Liver, to active metabolite 6-methoxy-2-naphthylacetic acid; 6-MNA
Elimination half-life	23 hours (active metabolite)
Excretion	Kidney
Identifiers
	IUPAC name 4-(6-methoxy-2-naphthyl)-2-butanone;
CAS Number	42924-53-8 ;
PubChem CID	4409;
IUPHAR/BPS	7245;
DrugBank	DB00461 ;
ChemSpider	4256 ;
UNII	LW0TIW155Z;
KEGG	D00425 ;
ChEBI	CHEBI:7443 ;
ChEMBL	ChEMBL1070 ;
CompTox Dashboard (EPA)	DTXSID4045472 ;
ECHA InfoCard	100.169.752
Chemical and physical data
Formula	C15H16O2
Molar mass	228.291 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(C)CCc1ccc2c(c1)ccc(OC)c2;
	InChI 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 ; Key:BLXXJMDCKKHMKV-UHFFFAOYSA-N ;
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Nabumetone, sold under the brand name Relafen among others, is a nonsteroidal anti-inflammatory drug (NSAID). Nabumetone was developed by Beecham and first received regulatory approval in 1991.

Nabumetone is a non-acidic NSAID prodrug that is rapidly metabolized in the liver to the active metabolite, 6-methoxy-2-naphthyl acetic acid. 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. There are two known polymorphs of the compound. Nabumetone has little effect on renal prostaglandin secretion and less of an association with heart failure than other traditional drugs of the class. Effects of nabumetone on blood pressure control in hypertensive patients on ACE inhibitors are also good, equivalent to paracetamol.

In 2023, it was the 271st most commonly prescribed medication in the United States, with more than 800,000 prescriptions.