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| Clinical data | |
|---|---|
| Trade names | Relafen |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a692022 |
| License data | |
| Routes of administration | By mouth |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Protein binding | > 99% (active metabolite) |
| Metabolism | Liver, to active metabolite 6-methoxy-2-naphthylacetic acid; 6-MNA |
| Eliminationhalf-life | 23 hours (active metabolite) |
| Excretion | Kidney |
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| IUPHAR/BPS | |
| DrugBank |
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| ChemSpider |
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| KEGG |
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| ChEBI | |
| ChEMBL | |
| 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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 N Y (what is this?) (verify) | |
Nabumetone, sold under the brand nameRelafen among others, is anonsteroidal anti-inflammatory drug (NSAID).[1][4] Nabumetone was developed byBeecham and first received regulatory approval in 1991.[5]
Nabumetone is a non-acidic NSAIDprodrug that is rapidly metabolized in the liver to the active metabolite, 6-methoxy-2-naphthyl acetic acid. Nabumetone's active metabolite inhibits thecyclooxygenase enzyme and preferentially blocksCOX-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, particularlyprostaglandins. It may be lessnephrotoxic thanindomethacin.[6] There are two knownpolymorphs of the compound.[7] Nabumetone has little effect on renalprostaglandin secretion and less of an association withheart failure than other traditional drugs of the class.[8] Effects of nabumetone on blood pressure control in hypertensive patients onACE inhibitors are also good,[clarification needed] equivalent toparacetamol.[9]
In 2023, it was the 271st most commonly prescribed medication in the United States, with more than 800,000 prescriptions.[10][11]
Nabumetone isindicated for relief of signs and symptoms of osteoarthritis and rheumatoid arthritis.[1]
Side effects includebloody orblack, 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; andringing in the ears.[12]
In October 2020, the USFood and Drug Administration (FDA) required theprescribing information 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.[13][14] They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.[13][14]
It is sold under many brand names, including Relafen,[1] Relifex, and Gambaran.
This article incorporates text from this source, which is in thepublic domain. This article incorporates text from this source, which is in thepublic domain.| pyrazolones / pyrazolidines | |
|---|---|
| salicylates | |
| acetic acid derivatives and related substances | |
| oxicams | |
| propionic acid derivatives (profens) |
|
| n-arylanthranilic acids (fenamates) | |
| COX-2 inhibitors (coxibs) | |
| other | |
| NSAID combinations | |
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;†withdrawn drugs;‡veterinary use. | |
