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Details

Stereochemistry ACHIRAL
Molecular Formula C15H16O2
Molecular Weight 228.2863
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NABUMETONE

SMILES

COC1=CC2=C(C=C1)C=C(CCC(C)=O)C=C2

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

2000
Primary
Nabumetone

Approved Use

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

Launch Date

2000
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
Use of nonsteroidal anti-inflammatory drugs and gastroprotective agents before the advent of cyclooxygenase-2-selective inhibitors: analysis of a large United States claims database.
2001 Dec
Cyclooxygenase-1 and cyclooxygenase-2 selectivity of non-steroidal anti-inflammatory drugs: investigation using human peripheral monocytes.
2001 Dec
The effects of nabumetone, a cyclooxygenase-2 inhibitor, on cisplatin-induced 5-hydroxytryptamine release from the isolated rat ileum.
2001 Jul-Aug
[Comparison of the efficacy and safety of nabumetone and diclofenac sodium in the treatment of patients with rheumatoid arthritis].
2001 May 10
Gastrointestinal medications and procedures in osteoarthritis patients treated with rofecoxib compared with nonselective NSAIDs.
2001 Nov 16
A comparison of adverse renovascular experiences among osteoarthritis patients treated with rofecoxib and comparator non-selective non-steroidal anti-inflammatory agents.
2002
2, 4-diamino-6- hydroxy pyrimidine inhibits NSAIDs induced nitrosyl-complex EPR signals and ulcer in rat jejunum.
2002 Apr 18
Dose-effect relationships of nonsteroidal anti-inflammatory drugs: a literature review.
2002 Aug
Drug-induced erythroderma with high fever.
2002 Feb
Nonsteroidal antiinflammatory drug-induced pseudoporphyria: a case series.
2002 Jul-Aug
A comparison of the effects of nabumetone vs meloxicam on serum thromboxane B2 and platelet function in healthy volunteers.
2002 Jun
The different patterns of blood pressure elevation by rofecoxib and nabumetone.
2002 Jun
Medication toxicity among patients with ankylosing spondylitis.
2002 Jun 15
Trends in medication use for osteoarthritis treatment.
2002 May
In vitro investigation of the effects of cyclooxygenase-2 inhibitors on contractile activity of the equine dorsal and ventral colon.
2002 Nov
Structure-function relationship and role of tumor necrosis factor-alpha-converting enzyme in the down-regulation of L-selectin by non-steroidal anti-inflammatory drugs.
2002 Oct 11
Drug-induced erythroderma with high fever--is it drug hypersensitivity syndrome?
2003 Apr
An open label study to establish dosing recommendations for nabumetone in juvenile rheumatoid arthritis.
2003 Apr
Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro.
2003 Aug
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
Effects of nabumetone, celecoxib, and ibuprofen on blood pressure control in hypertensive patients on angiotensin converting enzyme inhibitors.
2003 Feb
Determination of nabumetone in pharmaceutical formulation by flow injection analysis (FIA) with UV-detection.
2003 Jan
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
Nabumetone: therapeutic use and safety profile in the management of osteoarthritis and rheumatoid arthritis.
2004
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
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
Calculation of cyclodextrin binding affinities: energy, entropy, and implications for drug design.
2004 Nov
[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
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
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
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
Picture of the month. Stevens-Johnson Syndrome.
2006 Aug
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
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 MONOGRAPH]
Common Name English
Nabumetone [WHO-DD]
Common Name English
NABUMETONE [MI]
Common Name English
NABUMETONE [EP MONOGRAPH]
Common Name English
NABUMETONE [USP IMPURITY]
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
Classification Tree Code System Code
WHO-ATC M01AX01
Created by admin on Fri Dec 15 15:47:12 GMT 2023 , Edited by admin on Fri Dec 15 15:47:12 GMT 2023
FDA ORPHAN DRUG 255207
Created by admin on Fri Dec 15 15:47:12 GMT 2023 , Edited by admin on Fri Dec 15 15:47:12 GMT 2023
NCI_THESAURUS C54679
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WHO-VATC QM01AX01
Created by admin on Fri Dec 15 15:47:12 GMT 2023 , Edited by admin on Fri Dec 15 15:47:12 GMT 2023
NDF-RT N0000000160
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NDF-RT N0000175722
Created by admin on Fri Dec 15 15:47:12 GMT 2023 , Edited by admin on Fri Dec 15 15:47:12 GMT 2023
NCI_THESAURUS C257
Created by admin on Fri Dec 15 15:47:12 GMT 2023 , Edited by admin on Fri Dec 15 15:47:12 GMT 2023
NDF-RT N0000175721
Created by admin on Fri Dec 15 15:47:12 GMT 2023 , Edited by admin on Fri Dec 15 15:47:12 GMT 2023
LIVERTOX NBK548909
Created by admin on Fri Dec 15 15:47:12 GMT 2023 , Edited by admin on Fri Dec 15 15:47:12 GMT 2023
Code System Code Type Description
SMS_ID
100000092274
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PRIMARY
LACTMED
Nabumetone
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PRIMARY
DAILYMED
LW0TIW155Z
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PRIMARY
CHEBI
7443
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PRIMARY
RXCUI
31448
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PRIMARY RxNorm
RS_ITEM_NUM
1449518
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PRIMARY
NCI_THESAURUS
C47627
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PRIMARY
EVMPD
SUB09107MIG
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PRIMARY
MERCK INDEX
m7698
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PRIMARY Merck Index
DRUG BANK
DB00461
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PRIMARY
CAS
42924-53-8
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PRIMARY
MESH
C035605
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PRIMARY
INN
4855
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PRIMARY
ChEMBL
CHEMBL1070
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PRIMARY
PUBCHEM
4409
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PRIMARY
EPA CompTox
DTXSID4045472
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PRIMARY
IUPHAR
7245
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PRIMARY
WIKIPEDIA
NABUMETONE
Created by admin on Fri Dec 15 15:47:12 GMT 2023 , Edited by admin on Fri Dec 15 15:47:12 GMT 2023
PRIMARY
FDA UNII
LW0TIW155Z
Created by admin on Fri Dec 15 15:47:12 GMT 2023 , Edited by admin on Fri Dec 15 15:47:12 GMT 2023
PRIMARY
CHEBI
76252
Created by admin on Fri Dec 15 15:47:12 GMT 2023 , Edited by admin on Fri Dec 15 15:47:12 GMT 2023
PRIMARY
NSC
758623
Created by admin on Fri Dec 15 15:47:12 GMT 2023 , Edited by admin on Fri Dec 15 15:47:12 GMT 2023
PRIMARY
DRUG CENTRAL
1863
Created by admin on Fri Dec 15 15:47:12 GMT 2023 , Edited by admin on Fri Dec 15 15:47:12 GMT 2023
PRIMARY