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Details

Stereochemistry ACHIRAL
Molecular Formula C15H16O2
Molecular Weight 228.2869
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NABUMETONE

SMILES

CC(=O)CCc1ccc2cc(ccc2c1)OC

InChI

InChIKey=BLXXJMDCKKHMKV-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/cdi/nabumetone.html

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. 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. Nabumetone is used for acute and chronic treatment of signs and symptoms of osteoarthritis and rheumatoid arthritis. Nabumetone has been developed by Beecham. It is available under numerous brand names, such as Relafen, Relifex, and Gambaran.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
149.0 µM [IC50]
230.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nabumetone

Approved Use

Nabumetone tablets are indicated for relief of signs and symptoms of osteoarthritis and rheumatoid arthritis.

Launch Date

9.5921281E11
Primary
Nabumetone

Approved Use

Nabumetone tablets are indicated for relief of signs and symptoms of osteoarthritis and rheumatoid arthritis.

Launch Date

9.5921281E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
52.3 μg/mL
1000 mg 1 times / day steady-state, oral
dose: 1000 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
66.7 μg/mL
1000 mg 1 times / day steady-state, oral
dose: 1000 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
21.9 μg/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
33.7 μg/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
13.48 ng/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NABUMETONE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1022 μg × h/mL
1000 mg 1 times / day steady-state, oral
dose: 1000 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1270 μg × h/mL
1000 mg 1 times / day steady-state, oral
dose: 1000 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1120 μg × h/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2150 μg × h/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
204.98 ng × h/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NABUMETONE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
27.5 h
1000 mg 1 times / day steady-state, oral
dose: 1000 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
34.2 h
1000 mg 1 times / day steady-state, oral
dose: 1000 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
26.3 h
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
38.8 h
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
6-METHOXY-2-NAPHTHYLACETIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
16.82 h
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NABUMETONE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 g 1 times / day steady, oral (max)
Recommended
Dose: 2 g, 1 times / day
Route: oral
Route: steady
Dose: 2 g, 1 times / day
Sources: Page: 9
unhealthy, adult
n = 1677
Health Status: unhealthy
Condition: rheumatoid arthritis and osteoarthritis
Age Group: adult
Sex: unknown
Population Size: 1677
Sources: Page: 9
Disc. AE: Diarrhea, Dyspepsia...
AEs leading to
discontinuation/dose reduction:
Diarrhea (1.3%)
Dyspepsia (0.8%)
Abdominal pain (1.1%)
Sources: Page: 9
AEs

AEs

AESignificanceDosePopulation
Dyspepsia 0.8%
Disc. AE
2 g 1 times / day steady, oral (max)
Recommended
Dose: 2 g, 1 times / day
Route: oral
Route: steady
Dose: 2 g, 1 times / day
Sources: Page: 9
unhealthy, adult
n = 1677
Health Status: unhealthy
Condition: rheumatoid arthritis and osteoarthritis
Age Group: adult
Sex: unknown
Population Size: 1677
Sources: Page: 9
Abdominal pain 1.1%
Disc. AE
2 g 1 times / day steady, oral (max)
Recommended
Dose: 2 g, 1 times / day
Route: oral
Route: steady
Dose: 2 g, 1 times / day
Sources: Page: 9
unhealthy, adult
n = 1677
Health Status: unhealthy
Condition: rheumatoid arthritis and osteoarthritis
Age Group: adult
Sex: unknown
Population Size: 1677
Sources: Page: 9
Diarrhea 1.3%
Disc. AE
2 g 1 times / day steady, oral (max)
Recommended
Dose: 2 g, 1 times / day
Route: oral
Route: steady
Dose: 2 g, 1 times / day
Sources: Page: 9
unhealthy, adult
n = 1677
Health Status: unhealthy
Condition: rheumatoid arthritis and osteoarthritis
Age Group: adult
Sex: unknown
Population Size: 1677
Sources: Page: 9
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Comparative biotransformation and disposition studies of nabumetone in humans and minipigs using high-performance liquid chromatography with ultraviolet, fluorescence and mass spectrometric detection.
2003 Aug 8
Safe full-dose one-step nabumetone challenge in patients with nonsteroidal anti-inflammatory drug hypersensitivity.
2003 Jul-Aug
Analysis of nabumetone in human plasma by HPLC. Application to single dose pharmacokinetic studies.
2003 Jun 1
Risk of cancer in a large cohort of nonaspirin NSAID users: a population-based study.
2003 Jun 2
[Meta-analysis on the effect and adverse reaction on patients with osteoarthritis and rheumatoid arthritis treated with non-steroidal anti-inflammatory drugs].
2003 Nov
Selective COX-2 inhibition and cardiovascular effects: a review of the rofecoxib development program.
2003 Oct
Nabumetone: therapeutic use and safety profile in the management of osteoarthritis and rheumatoid arthritis.
2004
Spontaneous reports of hypertension leading to hospitalisation in association with rofecoxib, celecoxib, nabumetone and oxaprozin.
2004
Risk of breast cancer among users of aspirin and other anti-inflammatory drugs.
2004 Aug 2
Application of pentafluorophenyl hydrazine derivatives to the analysis of nabumetone and testosterone in human plasma by liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry.
2004 Dec
In vitro investigation of the effects of nonsteroidal anti-inflammatory drugs, prostaglandin E2, and prostaglandin F2alpha on contractile activity of the third compartment of the stomach of llamas.
2004 Feb
General principles of pharmaceutical solid polymorphism: a supramolecular perspective.
2004 Feb 23
Incremental cost-effectiveness of cyclooxygenase 2-selective versus nonselective nonsteroidal anti-inflammatory drugs in a cohort of coumarin users: a pharmacoeconomic analysis linked to a case-control study.
2004 Jul
Regulation of metalloproteinases and NF-kappaB activation in rabbit synovial fibroblasts via E prostaglandins and Erk: contrasting effects of nabumetone and 6MNA.
2004 Jul
Adverse effect of drug-induced emotional problems on work and daily activities. A principal component as an independent predictor of ADRs in Shanghai patients with osteo-arthropathy taking nabumetone.
2004 Jun
Risk factors of adverse drug reaction from non-steroidal anti-inflammatory drugs in Shanghai patients with arthropathy.
2004 Mar
Identification and determination of phase II nabumetone metabolites by high-performance liquid chromatography with photodiode array and mass spectrometric detection.
2004 Mar 26
Effects of dietary anticarcinogens and nonsteroidal anti-inflammatory drugs on rat gastrointestinal UDP-glucuronosyltransferases.
2004 Mar-Apr
A population based historical cohort study of the mortality associated with nabumetone, Arthrotec, diclofenac, and naproxen.
2004 May
Efficacy and safety of rofecoxib 12.5 mg versus nabumetone 1,000 mg in patients with osteoarthritis of the knee: a randomized controlled trial.
2004 May
Pain management in osteoarthritis: a focus on onset of efficacy--a comparison of rofecoxib, celecoxib, acetaminophen, and nabumetone across four clinical trials.
2004 Nov
Calculation of cyclodextrin binding affinities: energy, entropy, and implications for drug design.
2004 Nov
Systematic review: is ingestion of paracetamol or non-steroidal anti-inflammatory drugs associated with exacerbations of inflammatory bowel disease?
2004 Nov 15
[Reflections on COX, Vioxx and Relifex. Increased cardiovascular risk following selective COX-2 inhibition].
2004 Nov 25
The upper gastrointestinal safety of rofecoxib vs. NSAIDs: an updated combined analysis.
2004 Oct
Effect of the addition of water-soluble polymers on the interfacial properties of aerosol OT vesicles.
2004 Oct 15
Patient characteristics associated with outpatient prescriptions for nabumetone and oxaprozin versus celecoxib and rofecoxib.
2005 Apr 1
Simplex optimization of the variables affecting the micelle-stabilized room temperature phosphorescence of 6-methoxy-2-naphthylacetic acid and its kinetic determination in human urine.
2005 Apr 1
Photosensitizing properties of 6-methoxy-2-naphthylacetic acid, the major metabolite of the phototoxic non-steroidal anti-inflammatory and analgesic drug nabumetone.
2005 Aug
Pulp-dentine complex changes and root resorption during intrusive orthodontic tooth movement in patients prescribed nabumetone.
2005 Jan
The nonsteroidal anti-inflammatory drug, nabumetone, differentially inhibits beta-catenin signaling in the MIN mouse and azoxymethane-treated rat models of colon carcinogenesis.
2005 Jan 20
Rofecoxib for osteoarthritis.
2005 Jan 25
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Development and validation of a reversed-phase liquid chromatographic method for separation and simultaneous determination of COX-2 inhibitors in pharmaceuticals and its application to biological fluids.
2005 Jun
Subjective impact of osteoarthritis flare-ups on patients' quality of life.
2005 Mar 16
Cyclo-oxygenase 2 inhibitor, nabumetone, inhibits proliferation in chronic myeloid leukemia cell lines.
2005 May
Comparative effects of indomethacin and nabumetone on urine and electrolyte output in conscious rats.
2005 Nov
Risk of hospitalization with peptic ulcer disease or gastrointestinal hemorrhage associated with nabumetone, Arthrotec, diclofenac, and naproxen in a population based cohort study.
2005 Nov
Long-term use of non-steroidal anti-inflammatory drugs and the risk of myocardial infarction in the general population.
2005 Nov 29
Low direct cytotoxicity of nabumetone on gastric mucosal cells.
2005 Sep
Temporal relationship between use of NSAIDs, including selective COX-2 inhibitors, and cardiovascular risk.
2006
Tolerance of diclofenac after hypersensitivity to celecoxib and to nabumetone.
2006 Apr
Picture of the month. Stevens-Johnson Syndrome.
2006 Aug
Treatment of patients with osteoarthritis with rofecoxib compared with nabumetone.
2006 Feb
Prevalence and mechanism of nonsteroidal anti-inflammatory drug-induced clinical relapse in patients with inflammatory bowel disease.
2006 Feb
Evaluation of hydroxyimine as cytochrome P450-selective prodrug structure.
2006 Feb 9
NSAID use and the risk of hospitalization for first myocardial infarction in the general population: a nationwide case-control study from Finland.
2006 Jul
Comparison of Anti-inflammatory Activities of Six Curcuma Rhizomes: A Possible Curcuminoid-independent Pathway Mediated by Curcuma phaeocaulis Extract.
2006 Jun
A systematic investigation of recovery in preparative reverse phase high performance liquid chromatography/mass spectrometry.
2006 Jun 30
Spherical agglomeration of mefenamic acid and nabumetone to improve micromeritics and solubility: a technical note.
2006 May 26
Patents

Sample Use Guides

Initial dose: 1000 mg orally once a day Maintenance dose: 1500 to 2000 mg orally per day in 1 or 2 divided doses Maximum dose: 2000 mg/day
Route of Administration: Oral
Nabumetone (50 ug/ml) was found to significantly increase COX-2 at mRNA levels but directly suppress the concentration of PGE2 in culture medium of human intervertebral disc cells.
Name Type Language
NABUMETONE
EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
NABUMETONE [VANDF]
Common Name English
NABUMETONE [USP-RS]
Common Name English
BRL-14777
Code English
NABUMETONE [ORANGE BOOK]
Common Name English
NABUMETONE [JAN]
Common Name English
NABUMETONE [MART.]
Common Name English
2-BUTANONE, 4-(6-METHOXY-2-NAPHTHALENYL)-
Systematic Name English
NABUMETONE [USP]
Common Name English
NABUMETONE [USP MONOGRAPH]
Common Name English
NABUMETONE [MI]
Common Name English
NABUMETONE [EP MONOGRAPH]
Common Name English
RELAFEN
Brand Name English
NABUMETONE [INN]
Common Name English
4-(6-METHOXY-2-NAPHTHYL)-2-BUTANONE
Systematic Name English
NABUMETONE [USAN]
Common Name English
NSC-758623
Code English
NABUMETONE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC M01AX01
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
FDA ORPHAN DRUG 255207
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
NCI_THESAURUS C54679
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
WHO-VATC QM01AX01
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
NDF-RT N0000000160
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
NDF-RT N0000175722
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
NCI_THESAURUS C257
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
NDF-RT N0000175721
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
LIVERTOX 658
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
Code System Code Type Description
LACTMED
Nabumetone
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY
RXCUI
31448
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C47627
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY
EVMPD
SUB09107MIG
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY
MERCK INDEX
M7698
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB00461
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY
CAS
42924-53-8
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY
USP_CATALOG
1449518
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY USP-RS
MESH
C035605
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY
INN
4855
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY
ChEMBL
CHEMBL1070
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY
PUBCHEM
4409
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY
EPA CompTox
42924-53-8
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY
IUPHAR
7245
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY
WIKIPEDIA
NABUMETONE
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY
FDA UNII
LW0TIW155Z
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY
DRUG CENTRAL
1863
Created by admin on Fri Jun 25 21:00:31 UTC 2021 , Edited by admin on Fri Jun 25 21:00:31 UTC 2021
PRIMARY