Clinical data | |
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Trade names | Relafen |
AHFS/Drugs.com | Monograph |
MedlinePlus | a692022 |
License data |
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Routes of administration | By mouth |
ATC code | |
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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 |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.169.752 |
Chemical and physical data | |
Formula | C15H16O2 |
Molar mass | 228.291 g·mol−1 |
3D model (JSmol) | |
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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]