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
Molecular Formula | C15H16O2 |
Molecular Weight | 228.2863 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 Date2000 |
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Primary | Nabumetone Approved UseNabumetone tablets are indicated for relief of signs and symptoms of osteoarthritis and rheumatoid arthritis. Launch Date2000 |
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 |
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COX-2: where are we in 2003?--distinction from NSAIDs becoming blurred. | 2003 |
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Drug-induced erythroderma with high fever--is it drug hypersensitivity syndrome? | 2003 Apr |
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An open label study to establish dosing recommendations for nabumetone in juvenile rheumatoid arthritis. | 2003 Apr |
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[Nabumetone is an alternative]. | 2003 Apr 24 |
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Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro. | 2003 Aug |
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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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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 |
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Development of apoptosis-resistant dihydrofolate reductase-deficient Chinese hamster ovary cell line. | 2003 Jun 30 |
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[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 |
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Nabumetone: therapeutic use and safety profile in the management of osteoarthritis and rheumatoid arthritis. | 2004 |
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Spontaneous reports of hypertension leading to hospitalisation in association with rofecoxib, celecoxib, nabumetone and oxaprozin. | 2004 |
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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 |
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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 |
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General principles of pharmaceutical solid polymorphism: a supramolecular perspective. | 2004 Feb 23 |
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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 |
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Risk factors of adverse drug reaction from non-steroidal anti-inflammatory drugs in Shanghai patients with arthropathy. | 2004 Mar |
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Identification and determination of phase II nabumetone metabolites by high-performance liquid chromatography with photodiode array and mass spectrometric detection. | 2004 Mar 26 |
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Effects of dietary anticarcinogens and nonsteroidal anti-inflammatory drugs on rat gastrointestinal UDP-glucuronosyltransferases. | 2004 Mar-Apr |
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A population based historical cohort study of the mortality associated with nabumetone, Arthrotec, diclofenac, and naproxen. | 2004 May |
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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 |
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Pain management in osteoarthritis: a focus on onset of efficacy--a comparison of rofecoxib, celecoxib, acetaminophen, and nabumetone across four clinical trials. | 2004 Nov |
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Calculation of cyclodextrin binding affinities: energy, entropy, and implications for drug design. | 2004 Nov |
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Systematic review: is ingestion of paracetamol or non-steroidal anti-inflammatory drugs associated with exacerbations of inflammatory bowel disease? | 2004 Nov 15 |
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[Reflections on COX, Vioxx and Relifex. Increased cardiovascular risk following selective COX-2 inhibition]. | 2004 Nov 25 |
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The upper gastrointestinal safety of rofecoxib vs. NSAIDs: an updated combined analysis. | 2004 Oct |
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Effect of the addition of water-soluble polymers on the interfacial properties of aerosol OT vesicles. | 2004 Oct 15 |
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Patient characteristics associated with outpatient prescriptions for nabumetone and oxaprozin versus celecoxib and rofecoxib. | 2005 Apr 1 |
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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 |
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Pulp-dentine complex changes and root resorption during intrusive orthodontic tooth movement in patients prescribed nabumetone. | 2005 Jan |
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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 |
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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 |
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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 |
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Treatment of patients with osteoarthritis with rofecoxib compared with nabumetone. | 2006 Feb |
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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 |
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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 |
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.
Substance Class |
Chemical
Created
by
admin
on
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Fri Dec 15 15:47:12 GMT 2023
by
admin
on
Fri Dec 15 15:47:12 GMT 2023
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Record UNII |
LW0TIW155Z
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Record Status |
Validated (UNII)
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Record Version |
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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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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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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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METABOLIC ENZYME -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE ACTIVE -> PARENT |
has anti-inflammatory activity in animals; more potent inhibitor of prostaglandin synthesis than nabumetone
MAJOR
PLASMA
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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AT STEADY-STATE |
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Tmax | PHARMACOKINETIC |
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DOSE |
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