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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:: 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 µM [IC50]
230 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

959212800000
Primary
Nabumetone

Approved Use

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

Launch Date

959212800000
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
Recommended
Dose: 2 g, 1 times / day
Route: oral
Route: steady
Dose: 2 g, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Disc. AE: Diarrhea, Dyspepsia...
AEs leading to
discontinuation/dose reduction:
Diarrhea (1.3%)
Dyspepsia (0.8%)
Abdominal pain (1.1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Dyspepsia 0.8%
Disc. AE
2 g 1 times / day steady, oral
Recommended
Dose: 2 g, 1 times / day
Route: oral
Route: steady
Dose: 2 g, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Abdominal pain 1.1%
Disc. AE
2 g 1 times / day steady, oral
Recommended
Dose: 2 g, 1 times / day
Route: oral
Route: steady
Dose: 2 g, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Diarrhea 1.3%
Disc. AE
2 g 1 times / day steady, oral
Recommended
Dose: 2 g, 1 times / day
Route: oral
Route: steady
Dose: 2 g, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Non-steroidal anti-inflammatory drugs inhibit the expression of cytokines and induce HSP70 in human monocytes.
1999 May
Rofecoxib: a review of its use in the management of osteoarthritis, acute pain and rheumatoid arthritis.
2001
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.
2001
Effect of nabumetone and aspirin on colonic mucosal bleeding time.
2001 Apr
Inhibitors of cyclooxygenase-2 (COX-2) suppressed the proliferation and differentiation of human leukaemia cell lines.
2001 Aug
Cyclooxygenase selectivity of non-steroid anti-inflammatory drugs in humans: ex vivo evaluation.
2001 Aug 24
Comparison of the efficacy and safety of naproxen CR and nabumetone in the treatment of patients with osteoarthritis of the knee.
2001 Dec
The ever-emerging anti-inflammatories. Have there been any real advances?
2001 Jan-Dec
Prolonged activation of mitogen-activated protein kinases during NSAID-induced apoptosis in HT-29 colon cancer cells.
2001 Jun
[Comparison of the efficacy and safety of nabumetone and diclofenac sodium in the treatment of patients with rheumatoid arthritis].
2001 May 10
[Evaluation of early biomarkers of cartilage degeneration in the diagnosis and clinico-therapeutic monitoring of primary osteoarthrosis].
2001 May-Jun
[Side effects cause enormous costs. Expensive arthritis therapy].
2001 Nov 15
Gastrointestinal medications and procedures in osteoarthritis patients treated with rofecoxib compared with nonselective NSAIDs.
2001 Nov 16
Cardiovascular thrombotic events in controlled, clinical trials of rofecoxib.
2001 Nov 6
Nonsteroidal anti-inflammatory drugs for perioperative pain control.
2001 Oct
2, 4-diamino-6- hydroxy pyrimidine inhibits NSAIDs induced nitrosyl-complex EPR signals and ulcer in rat jejunum.
2002 Apr 18
Comparison of cardiovascular thrombotic events in patients with osteoarthritis treated with rofecoxib versus nonselective nonsteroidal anti-inflammatory drugs (ibuprofen, diclofenac, and nabumetone).
2002 Jan 15
A comparison of the effects of nabumetone vs meloxicam on serum thromboxane B2 and platelet function in healthy volunteers.
2002 Jun
Medication toxicity among patients with ankylosing spondylitis.
2002 Jun 15
[Nabumetone is an alternative].
2003 Apr 24
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
Non-steroidal anti-inflammatory drug, nabumetone, prevents indometacin-induced gastric damage via inhibition of neutrophil functions.
2003 Feb
Effects of nabumetone, celecoxib, and ibuprofen on blood pressure control in hypertensive patients on angiotensin converting enzyme inhibitors.
2003 Feb
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
Spontaneous reports of hypertension leading to hospitalisation in association with rofecoxib, celecoxib, nabumetone and oxaprozin.
2004
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
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
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
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
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
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
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
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
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
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