Contents

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: WARNING[1]
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 Y
PubChem CID	4409
IUPHAR/BPS	7245
DrugBank	DB00461 Y
ChemSpider	4256 Y
UNII	LW0TIW155Z
KEGG	D00425 Y
ChEBI	CHEBI:7443 N
ChEMBL	ChEMBL1070 Y
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 Y Key:BLXXJMDCKKHMKV-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Nabumetone, sold under the brand name Relafen among others, is a nonsteroidal anti-inflammatory drug (NSAID).^[3] Nabumetone was developed by Beecham and first received regulatory approval in 1991.^[4]

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.^[5] There are two known polymorphs of the compound.^[6] Nabumetone has little effect on renal prostaglandin secretion and less of an association with heart failure than other traditional drugs of the class.^[7] Effects of nabumetone on blood pressure control in hypertensive patients on ACE inhibitors are also good,^{[clarification needed]} equivalent to paracetamol.^[8]

In 2021, it was the 250th most commonly prescribed medication in the United States, with more than 1 million prescriptions.^[9][10]

Medical uses[edit]

Nabumetone is used to treat pain and inflammation.^{[citation needed]}

Side effects[edit]

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

Side effects include bloodyorblack, tarry stools; change in color, frequency, or amount of urine; chest pain; shortness of breath; coughing up blood; pale stools; numbness; weakness; flu-like symptoms; leg pain; vision problems; speech problems; problems walking; weight gain; stomach pain; cold sweat; skin rash; blisters; headache; swelling; bleeding; bruising; vomiting blood; jaundice; diarrhea; constipation; dizziness; indigestion; gas; nausea; and ringing in the ears.^[11]

In October 2020, the U.S. Food and Drug Administration (FDA) required the drug label to be updated for all nonsteroidal anti-inflammatory medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid.^[12][13] They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.^[12][13]

Society and culture[edit]

Brand names[edit]

It is available under numerous brand names, including Relafen, Relifex, and Gambaran.

References[edit]

^ ^{a b} "FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications". U.S. Food and Drug Administration (FDA) (Press release). 15 October 2020. Retrieved 15 October 2020. This article incorporates text from this source, which is in the public domain.

^ ^{a b} "NSAIDs may cause rare kidney problems in unborn babies". U.S. Food and Drug Administration. 21 July 2017. Retrieved 15 October 2020. This article incorporates text from this source, which is in the public domain.