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
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
DescriptionSources: http://www.drugbank.ca/drugs/DB00461Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/cdi/nabumetone.html
Sources: http://www.drugbank.ca/drugs/DB00461
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL221 Sources: http://www.drugbank.ca/drugs/DB00461 |
149.0 µM [IC50] | ||
Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00461 |
230.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Nabumetone Approved UseNabumetone tablets are indicated for relief of signs and symptoms of osteoarthritis and rheumatoid arthritis. Launch Date9.5921281E11 |
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Primary | Nabumetone Approved UseNabumetone tablets are indicated for relief of signs and symptoms of osteoarthritis and rheumatoid arthritis. Launch Date9.5921281E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
52.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12763542/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1022 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12763542/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
27.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12763542/ |
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
Dose | Population | Adverse 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%) Sources: Page: 9Dyspepsia (0.8%) Abdominal pain (1.1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
PubMed
Title | Date | PubMed |
---|---|---|
Renal effects of nabumetone, a COX-2 antagonist: impairment of function in isolated perfused rat kidneys contrasts with preserved renal function in vivo. | 2001 |
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Cyclooxygenase selectivity of non-steroid anti-inflammatory drugs in humans: ex vivo evaluation. | 2001 Aug 24 |
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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 |
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Cyclooxygenase-1 and cyclooxygenase-2 selectivity of non-steroidal anti-inflammatory drugs: investigation using human peripheral monocytes. | 2001 Dec |
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Comparison of the efficacy and safety of naproxen CR and nabumetone in the treatment of patients with osteoarthritis of the knee. | 2001 Dec |
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Effects of NSAIDs on cryoprobe-induced gastric ulcer healing in rats. | 2001 Dec |
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The ever-emerging anti-inflammatories. Have there been any real advances? | 2001 Jan-Dec |
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The effects of nabumetone, a cyclooxygenase-2 inhibitor, on cisplatin-induced 5-hydroxytryptamine release from the isolated rat ileum. | 2001 Jul-Aug |
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[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 |
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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 |
|
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 |
|
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 |
|
Nonsteroidal antiinflammatory drug-induced pseudoporphyria: a case series. | 2002 Jul-Aug |
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A comparison of the effects of nabumetone vs meloxicam on serum thromboxane B2 and platelet function in healthy volunteers. | 2002 Jun |
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The different patterns of blood pressure elevation by rofecoxib and nabumetone. | 2002 Jun |
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Medication toxicity among patients with ankylosing spondylitis. | 2002 Jun 15 |
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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 |
|
COX-2: where are we in 2003?--distinction from NSAIDs becoming blurred. | 2003 |
|
[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 |
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Non-steroidal anti-inflammatory drug, nabumetone, prevents indometacin-induced gastric damage via inhibition of neutrophil functions. | 2003 Feb |
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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 |
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Safe full-dose one-step nabumetone challenge in patients with nonsteroidal anti-inflammatory drug hypersensitivity. | 2003 Jul-Aug |
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Analysis of nabumetone in human plasma by HPLC. Application to single dose pharmacokinetic studies. | 2003 Jun 1 |
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Risk of cancer in a large cohort of nonaspirin NSAID users: a population-based study. | 2003 Jun 2 |
|
Development of apoptosis-resistant dihydrofolate reductase-deficient Chinese hamster ovary cell line. | 2003 Jun 30 |
|
[Meta-analysis on the effect and adverse reaction on patients with osteoarthritis and rheumatoid arthritis treated with non-steroidal anti-inflammatory drugs]. | 2003 Nov |
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Selective COX-2 inhibition and cardiovascular effects: a review of the rofecoxib development program. | 2003 Oct |
|
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 |
|
General principles of pharmaceutical solid polymorphism: a supramolecular perspective. | 2004 Feb 23 |
|
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 |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Subjective impact of osteoarthritis flare-ups on patients' quality of life. | 2005 Mar 16 |
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Comparative effects of indomethacin and nabumetone on urine and electrolyte output in conscious rats. | 2005 Nov |
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Long-term use of non-steroidal anti-inflammatory drugs and the risk of myocardial infarction in the general population. | 2005 Nov 29 |
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Temporal relationship between use of NSAIDs, including selective COX-2 inhibitors, and cardiovascular risk. | 2006 |
|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/nabumetone.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18976171
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.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
M01AX01
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FDA ORPHAN DRUG |
255207
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NCI_THESAURUS |
C54679
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WHO-VATC |
QM01AX01
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NDF-RT |
N0000000160
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NDF-RT |
N0000175722
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NCI_THESAURUS |
C257
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NDF-RT |
N0000175721
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LIVERTOX |
NBK548909
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100000092274
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Nabumetone
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LW0TIW155Z
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7443
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31448
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1449518
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C47627
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SUB09107MIG
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M7698
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DB00461
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42924-53-8
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C035605
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4855
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CHEMBL1070
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4409
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DTXSID4045472
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7245
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NABUMETONE
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LW0TIW155Z
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76252
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758623
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1863
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)