Drug/Small Molecule:
nabumetone

2D structure

Overview

Generic Names: Nabumetona; Nabumetonum [INN-Latin]
Trade Names: Arthaxan; Balmox; Consolan; Dolsinal; Flambate; Listran; Mebutan; Nabuser; Prodac; Relafen; Relif; Relifen; Relifex; Unimetone
PharmGKB Accession Id: PA450572

Description

Nabumetone is a non-steroidal anti-inflammatory drug of the arylalkanoic acid family (which includes diclofenac). Marketed under the brand name Relafen, it has been shown to have a slightly lower risk of gastrointestinal side effects than most other non-selective NSAID's. (source: Drug Bank)

Indication

For acute and chronic treatment of signs and symptoms of osteoarthritis and rheumatoid arthritis. (source: Drug Bank)

ATC Therapeutic Category

  • M01AX:Other antiinflammatory and antirheumatic agents, non-steroids

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

The parent compound is a prodrug, which undergoes hepatic biotransformation to the active component, 6-methoxy-2-naphthylacetic acid (6MNA), that is a potent inhibitor of prostaglandin synthesis, most likely through binding to the COX-1 and COX-2 receptors. (source: Drug Bank)

Pharmacology

Nabumetone is a naphthylalkanone. It is a nonsteroidal anti-inflammatory drug (NSAID) that exhibits anti-inflammatory, analgesic and antipyretic properties in pharmacologic studies. As with other nonsteroidal anti-inflammatory agents, its mode of action is not known. However, the ability to inhibit prostaglandin synthesis may be involved in the anti-inflammatory effect. (source: Drug Bank)

Food Interactions

Avoid alcohol.
Take with food for faster absorption. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Undergoes rapid biotransformation to the principal active metabolite, 6-methoxy-2-naphthylacetic acid (6MNA). Approximately 35% of a 1000 mg oral dose of nabumetone is converted to 6MNA and 50% is converted into unidentified metabolites which are subsequently excreted in the urine. (source: Drug Bank)

Protein Binding

The active metabolite, 6MNA, is more than 99% bound to plasma proteins. (source: Drug Bank)

Absorption

Well absorbed from the gastrointestinal tract. Coadministration of food increases the rate of absorption and subsequent appearance of 6MNA (the active metabolite) in the plasma but does not affect the extent of conversion of nabumetone into 6MNA. (source: Drug Bank)

Toxicity

The one overdose occurred in a 17-year-old female patient who had a history of abdominal pain and was hospitalized for increased abdominal pain following ingestion of 30 nabumetone tablets (15 grams total). Stools were negative for occult blood and there was no fall in serum hemoglobin concentration. The patient had no other symptoms. (source: Drug Bank)

Isomeric SMILES Code:

CC(=O)CCc1ccc2cc(ccc2c1)OC (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Has annotations
NR1I2
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  • FA
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Publications

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
PTGS1 Uncurated Annotation (source: Drug Bank)
PTGS2 Uncurated Annotation (source: Drug Bank)

PharmGKB Curated Pathways

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
acenocoumarol Uncurated Annotation The NSAID increases the anticoagulant effect (source: Drug Bank)
alendronate Uncurated Annotation Increased risk of gastric toxicity (source: Drug Bank)
cyclosporine Uncurated Annotation Monitor for nephrotoxicity (source: Drug Bank)
dicumarol Uncurated Annotation The NSAID increases the anticoagulant effect (source: Drug Bank)
methotrexate Uncurated Annotation The NSAID increases the effect and toxicity of methotrexate (source: Drug Bank)
warfarin Uncurated Annotation The NSAID increases the anticoagulant effect (source: Drug Bank)

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00461
KEGG Drug ID:
D00425
PubChem Compound ID:
4409
PubChem Substance ID:
7847491

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

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