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Identification
Name Nabumetone
Accession Number DB00461 (APRD01128)
Type small molecule
Groups approved
Description

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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Nabumetona
  • Nabumetonum [INN-Latin]
Brand names
  • 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
Brand name mixtures Not Available
Categories
  • Antineoplastic Agents
CAS number 42924-53-8
Weight Average: 228.2863
Monoisotopic: 228.115029756
Chemical Formula C15H16O2
InChI Key InChIKey=BLXXJMDCKKHMKV-UHFFFAOYSA-N
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
Plain Text
IUPAC Name
4-(6-methoxynaphthalen-2-yl)butan-2-one
SMILES
COC1=CC2=C(C=C1)C=C(CCC(C)=O)C=C2
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Naphthalenes
Substructures
  • Naphthalenes
  • Phenols and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Aromatic compounds
  • Anisoles
  • Phenyl Esters
  • Ketones
Pharmacology
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
Smp00114 Nabumetone Pathway SMP00114
Pharmacoeconomics
Manufacturers
  • Actavis elizabeth llc
  • Copley pharmaceutical inc
  • Dr reddys laboratories ltd
  • Invagen pharmaceuticals inc
  • Matrix laboratories ltd
  • Par pharmaceutical
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Smithkline beecham corp dba glaxosmithkline
Packagers
Dosage forms
Form Route Strength
Tablet, film coated Oral 500 mg
Tablet, film coated Oral 750 mg
Prices
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
Patents Not Available
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
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00425 Link_out
PubChem Compound 4409 Link_out
PubChem Substance 46507729 Link_out
ChemSpider 4256 Link_out
BindingDB 50240662 Link_out
Therapeutic Targets Database DAP000735 Link_out
PharmGKB PA450572 Link_out
Drug Product Database 2238639 Link_out
RxList http://www.rxlist.com/cgi/generic/nabume.htm Link_out
Drugs.com http://www.drugs.com/cdi/nabumetone.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/rel1370.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Nabumetone Link_out
ATC Codes
  • M01AX01
AHFS Codes
  • 28:08.04.92
PDB Entries Not Available
FDA label show (322 KB)
MSDS show (29.8 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid alcohol.
  • Take with food for faster absorption.
Targets

1. Prostaglandin G/H synthase 2

Pharmacological action: yes
Actions: inhibitor

May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity

Organism class: human
UniProt ID: P35354 Link_out
Gene: PTGS2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Fackovcova D, Kristova V, Kriska M: Renal damage induced by the treatment with non-opioid analgesics—theoretical assumption or clinical significance. Bratisl Lek Listy. 2000;101(8):417-22. Pubmed
  2. Roy HK, Karolski WJ, Ratashak A: Distal bowel selectivity in the chemoprevention of experimental colon carcinogenesis by the non-steroidal anti-inflammatory drug nabumetone. Int J Cancer. 2001 May 15;92(4):609-15. Pubmed
  3. van Kraaij DJ, Hovestad-Witterland AH, de Metz M, Vollaard EJ: A comparison of the effects of nabumetone vs meloxicam on serum thromboxane B2 and platelet function in healthy volunteers. Br J Clin Pharmacol. 2002 Jun;53(6):644-7. Pubmed
  4. Hedner T, Samulesson O, Wahrborg P, Wadenvik H, Ung KA, Ekbom A: Nabumetone: therapeutic use and safety profile in the management of osteoarthritis and rheumatoid arthritis. Drugs. 2004;64(20):2315-43; discussion 2344-5. Pubmed
  5. Elliott SN, McKnight W, Cirino G, Wallace JL: A nitric oxide-releasing nonsteroidal anti-inflammatory drug accelerates gastric ulcer healing in rats. Gastroenterology. 1995 Aug;109(2):524-30. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Prostaglandin G/H synthase 1

Pharmacological action: unknown
Actions: inhibitor

May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells

Organism class: human
UniProt ID: P23219 Link_out
Gene: PTGS1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Giuliano F, Ferraz JG, Pereira R, de Nucci G, Warner TD: Cyclooxygenase selectivity of non-steroid anti-inflammatory drugs in humans: ex vivo evaluation. Eur J Pharmacol. 2001 Aug 24;426(1-2):95-103. Pubmed
  2. Takeuchi K, Smale S, Premchand P, Maiden L, Sherwood R, Thjodleifsson B, Bjornsson E, Bjarnason I: Prevalence and mechanism of nonsteroidal anti-inflammatory drug-induced clinical relapse in patients with inflammatory bowel disease. Clin Gastroenterol Hepatol. 2006 Feb;4(2):196-202. Pubmed
  3. Cipollone F, Ganci A, Panara MR, Greco A, Cuccurullo F, Patrono C, Patrignani P: Effects of nabumetone on prostanoid biosynthesis in humans. Clin Pharmacol Ther. 1995 Sep;58(3):335-41. Pubmed
  4. Bensen W, Zizzo A: Newer, safer nonsteroidal anti-inflammatory drugs. Rational NSAID selection for arthritis. Can Fam Physician. 1998 Jan;44:101-2, 105-7. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:39

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.