Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H12O3 |
| Molecular Weight | 216.2326 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=CC=C(CC(O)=O)C=C2C=C1
InChI
InChIKey=PHJFLPMVEFKEPL-UHFFFAOYSA-N
InChI=1S/C13H12O3/c1-16-12-5-4-10-6-9(7-13(14)15)2-3-11(10)8-12/h2-6,8H,7H2,1H3,(H,14,15)
| Molecular Formula | C13H12O3 |
| Molecular Weight | 216.2326 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P23219|||Q5T7T7 Gene ID: 5742.0 Gene Symbol: PTGS1 Target Organism: Homo sapiens (Human) |
64.0 µM [IC50] | ||
Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) |
93.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Rapid simultaneous determination of four non-steroidal anti-inflammatory drugs by means of derivative nonlinear variable-angle synchronous fluorescence spectrometry. | 2010-08 |
|
| Pathway-Targeted Pharmacogenomics of CYP1A2 in Human Liver. | 2010 |
|
| Applicability of LC/MS/MS assay for 6-methoxy-2-napthylacetic acid to support the bioequivalence study of nabumetone-comments on the research work of Patel et al. (2008). | 2009-06 |
|
| A predominate role of CYP1A2 for the metabolism of nabumetone to the active metabolite, 6-methoxy-2-naphthylacetic acid, in human liver microsomes. | 2009-05 |
|
| Serum protein binding displacement: theoretical analysis using a hypothetical radiopharmaceutical and experimental analysis with 123I-N-isopropyl-p-iodoamphetamine. | 2009-01 |
|
| Effect of a nonprotein bioactive agent on the reduction of cyclooxygenase-2 and tumor necrosis factor-alpha in human intervertebral disc cells in vitro. | 2008-11 |
|
| High-throughput LC-MS/MS assay for 6-methoxy-2-naphthylacetic acid, an active metabolite of nabumetone in human plasma and its application to bioequivalence study. | 2008-11 |
|
| Theoretical study of the phototoxicity of naproxen and the active form of nabumetone. | 2008-10-30 |
|
| Simultaneous determination of two anti-inflammatory drugs in serum using isopotential fluorimetry. | 2008-09-05 |
|
| Safety of the nonselective NSAID nabumetone : focus on gastrointestinal tolerability. | 2008 |
|
| Synthesis and evaluation of some gastrointestinal sparing anti-inflammatory aminoethyl ester derivatives of naphthalene-based NSAIDs. | 2007-02 |
|
| Evaluation of hydroxyimine as cytochrome P450-selective prodrug structure. | 2006-02-09 |
|
| Low direct cytotoxicity of nabumetone on gastric mucosal cells. | 2005-09 |
|
| Photosensitizing properties of 6-methoxy-2-naphthylacetic acid, the major metabolite of the phototoxic non-steroidal anti-inflammatory and analgesic drug nabumetone. | 2005-08 |
|
| 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. | 2005-04-01 |
|
| Regulation of metalloproteinases and NF-kappaB activation in rabbit synovial fibroblasts via E prostaglandins and Erk: contrasting effects of nabumetone and 6MNA. | 2004-07 |
|
| Nabumetone: therapeutic use and safety profile in the management of osteoarthritis and rheumatoid arthritis. | 2004 |
|
| Comparative biotransformation and disposition studies of nabumetone in humans and minipigs using high-performance liquid chromatography with ultraviolet, fluorescence and mass spectrometric detection. | 2003-08-08 |
|
| Non-steroidal anti-inflammatory drug, nabumetone, prevents indometacin-induced gastric damage via inhibition of neutrophil functions. | 2003-02 |
|
| The role of cyclooxygenase-2 in lumbar disc herniation. | 2002-11-15 |
|
| 2, 4-diamino-6- hydroxy pyrimidine inhibits NSAIDs induced nitrosyl-complex EPR signals and ulcer in rat jejunum. | 2002-04-18 |
|
| Evidence for the involvement of cyclooxygenase activity in the development of cocaine sensitization. | 2002-01-29 |
|
| Renal effects of nabumetone, a COX-2 antagonist: impairment of function in isolated perfused rat kidneys contrasts with preserved renal function in vivo. | 2001 |
Sample Use Guides
In the indometacin-induced gastric mucosal injury, rats were treated with indometacin and then nabumetone or 6MNA (6-Methoxy-2-Naphthylacetic acid) was orally administered. Nabumetone prevented gastric damage accompanied by the reduction of neutrophil infiltration into gastric mucosa, but such an effect was not observed with 6MNA
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: 6MNA (6-Methoxy-2-Naphthylacetic acid) had variable effects on cyclooxygenase activity, depending on the concentration and was less potent and less effective than indomethacin. Sulphasalazine inhibited 15-PGDH in a concentration-dependent manner whereas 6MNA inhibited it only at high concentrations. Basal 5-lipoxy-genase (5-L) activity was attenuated by phenidone and unaltered by 6MNA but increased by nabumetone at the highest concentration. In the presence of arachidonic acid, to raise 5-LO activity, nabumetone, 6MNA, BW755C and phenidone apparently inhibited this activity. However, it was possible that both nabumetone and 6MNA inhibited a prostanoid-mediated stimulatory effect on 5-LO rather than effecting enzyme inhibition per se.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:11:02 GMT 2025
by
admin
on
Mon Mar 31 22:11:02 GMT 2025
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| Record UNII |
9H7K3YOD7Q
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| Record Status |
Validated (UNII)
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| Record Version |
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