Arthaxan (SmithKline Beecham (Germany; discontinued));Balmox (Beecham (Portugal), Meda (Switzerland));Consolan;Dolsinal (Ferrer (Spain; discontinued));Flambate;Listran (Uriach (Spain));Mebutan (Meda (Netherlands));Nabuser (Geymonat (Italy));Prodac;Relafen (GlaxoSmithKline (Canada, USA; discontinued));Relif (Meda (Spain));Relifen (Sanwa (Japan), GSK (South Africa));Relifex (Meda (Czeck Republic, Denmark, Finland, Germany, Greece, Hungary, Ireland, Italy, Norway, Sweden, United Kingdom), GSK (Israel, Mexico, Poland, Thailand, Turkey), SmithKline Beecham (Philippines));Unimetone;

Nabumetona;Nabumetonum [INN-Latin];

Nabumetone is a nonsteroidal anti-inflammatory drug (NSAID) 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 NSAIDs.

• Actavis elizabeth llc
• Copley pharmaceutical inc
• Dr reddys laboratories ltd
• Invagen pharmaceuticals inc
• Matrix laboratories ltd
• Par pharmaceutical
• Sandoz inc
• Smithkline beecham corp dba glaxosmithkline
• Teva pharmaceuticals usa inc

Synthesis Reference	Not Available
General Reference	Not Available

Form	Route	Strength
Tablet, film coated	Oral	500 mg
Tablet, film coated	Oral	750 mg

Unit description	Cost	Unit
Relafen 750 mg tablet	2.91 USD	tablet
Relafen 500 mg tablet	2.82 USD	tablet
Nabumetone 750 mg tablet	1.56 USD	tablet
Nabumetone 500 mg tablet	1.32 USD	tablet
Apo-Nabumetone 500 mg Tablet	0.39 USD	tablet
Mylan-Nabumetone 500 mg Tablet	0.39 USD	tablet
Novo-Nabumetone 500 mg Tablet	0.39 USD	tablet

Type	small molecule

Classes

Naphthalenes

Substructures

Naphthalenes Phenols and Derivatives Ethers Benzene and Derivatives Aromatic compounds Anisoles Phenyl Esters Ketones

ANTIINFLAMMATORY AND ANTIRHEUMATIC 消炎抗风湿;

Indication	For acute and chronic treatment of signs and symptoms of osteoarthritis and rheumatoid arthritis.
Pharmacodynamics	Nabumetone is a naphthylalkanone. Is is a non-selective prostaglandin G/H synthase (a.k.a. cyclooxygenase or COX) inhibitor that acts on both prostaglandin G/H synthase 1 and 2 (COX-1 and -2). Prostaglandin G/H synthase catalyzes the conversion of arachidonic acid to prostaglandin G2 and prostaglandin G2 to prostaglandin H2. Prostaglandin H2 is the precursor to a number of prostaglandins involved in fever, pain, swelling, inflammation, and platelet aggregation. The parent compound is a prodrug that undergoes hepatic biotransformation to the active compound, 6-methoxy-2-naphthylacetic acid (6MNA). The analgesic, antipyretic and anti-inflammatory effects of NSAIDs occur as a result of decreased prostaglandin synthesis.
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-2 and COX-1 receptors.
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.
Volume of distribution	Not Available
Protein binding	The active metabolite, 6MNA, is more than 99% bound to plasma proteins.
Metabolism	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.
Route of elimination	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.
Half life	Approximately 23 hours for the active metabolite, 6MNA. Increased in patients with renal insufficiency.
Clearance	20 – 30 mL/min
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.
Affected organisms	Humans and other mammals
Pathways	Pathway Name SMPDB ID Nabumetone Pathway SMP00114

Properties
State	solid
Melting point	Not Available
Experimental Properties	Property Value Source water solubility Practically insoluble PhysProp logP 3.1 PhysProp
Predicted Properties	Property Value Source water solubility 1.93e-03 g/l ALOGPS logP 3.41 ALOGPS logP 3.22 ChemAxon Molconvert logS -5.07 ALOGPS pKa ChemAxon Molconvert hydrogen acceptor count 2 ChemAxon Molconvert hydrogen donor count 0 ChemAxon Molconvert polar surface area 26.30 ChemAxon Molconvert rotatable bond count 4 ChemAxon Molconvert refractivity 68.43 ChemAxon Molconvert polarizability 26.17 ChemAxon Molconvert

Drug	Interaction
Acenocoumarol	The NSAID, nabumetone, may increase the anticoagulant effect of acenocoumarol.
Alendronate	Increased risk of gastric toxicity
Anisindione	The NSAID, nabumetone, may increase the anticoagulant effect anisindione.
Cyclosporine	Monitor for nephrotoxicity
Dicumarol	The NSAID, nabumetone, may increase the anticoagulant effect of dicumarol.
Ginkgo biloba	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Methotrexate	The NSAID, nabumetone, may decrease the renal excretion of methotrexate. Increased risk of methotrexate toxicity.
Telmisartan	Concomitant use of Telmisartan and Nabumetone may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Timolol	The NSAID, Nabumetone, may antagonize the antihypertensive effect of Timolol.
Trandolapril	The NSAID, Nabumetone, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Nabumetone is initiated, discontinued or dose changed.
Treprostinil	The prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Nabumetone. Monitor for increased bleeding during concomitant thearpy.
Warfarin	The antiplatelet effects of nabumetone may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.

• Avoid alcohol.
• Take with food for faster absorption.