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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
Structure of 6-METHOXY-2-NAPHTHYLACETIC ACID

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)

HIDE SMILES / InChI
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

Description

6-Methoxy-2-Naphthylacetic acid (6-MNA), an active metabolite of non-steroidal anti-inflammatory drug nabumetone has long half-life and has the tendency to penetrate well into synovial fluid. 6-MNA is a competitive inhibitor of Cox (cyclooxygenases).

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Prostaglandin G/H synthase 1
30
Target ID: P23219|||Q5T7T7
Gene ID: 5742.0
Gene Symbol: PTGS1
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 64.0 µM [IC50]
Prostaglandin G/H synthase 2
48
Target ID: P35354
Gene ID: 5743.0
Gene Symbol: PTGS2
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 93.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Renal effects of nabumetone, a COX-2 antagonist: impairment of function in isolated perfused rat kidneys contrasts with preserved renal function in vivo.
2001
2, 4-diamino-6- hydroxy pyrimidine inhibits NSAIDs induced nitrosyl-complex EPR signals and ulcer in rat jejunum.
2002 Apr 18
Evidence for the involvement of cyclooxygenase activity in the development of cocaine sensitization.
2002 Jan-Feb
The role of cyclooxygenase-2 in lumbar disc herniation.
2002 Nov 15
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
Nabumetone: therapeutic use and safety profile in the management of osteoarthritis and rheumatoid arthritis.
2004
Regulation of metalloproteinases and NF-kappaB activation in rabbit synovial fibroblasts via E prostaglandins and Erk: contrasting effects of nabumetone and 6MNA.
2004 Jul
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
Low direct cytotoxicity of nabumetone on gastric mucosal cells.
2005 Sep
Evaluation of hydroxyimine as cytochrome P450-selective prodrug structure.
2006 Feb 9
Synthesis and evaluation of some gastrointestinal sparing anti-inflammatory aminoethyl ester derivatives of naphthalene-based NSAIDs.
2007 Feb
Safety of the nonselective NSAID nabumetone : focus on gastrointestinal tolerability.
2008
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 Nov
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 Nov
Theoretical study of the phototoxicity of naproxen and the active form of nabumetone.
2008 Oct 30
Simultaneous determination of two anti-inflammatory drugs in serum using isopotential fluorimetry.
2008 Sep 5
Serum protein binding displacement: theoretical analysis using a hypothetical radiopharmaceutical and experimental analysis with 123I-N-isopropyl-p-iodoamphetamine.
2009 Jan
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 Jun
A predominate role of CYP1A2 for the metabolism of nabumetone to the active metabolite, 6-methoxy-2-naphthylacetic acid, in human liver microsomes.
2009 May
Pathway-Targeted Pharmacogenomics of CYP1A2 in Human Liver.
2010
Rapid simultaneous determination of four non-steroidal anti-inflammatory drugs by means of derivative nonlinear variable-angle synchronous fluorescence spectrometry.
2010 Aug
Patents

Patents

04048330
7
05281606
1
05596101
1

Sample Use Guides

In Vivo Use Guide
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 Sat Dec 16 08:35:00 GMT 2023
Edited
by admin
on Sat Dec 16 08:35:00 GMT 2023
Record UNII
9H7K3YOD7Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
6-METHOXY-2-NAPHTHYLACETIC ACID
Systematic Name English
NAPROXEN SODIUM IMPURITY I [EP IMPURITY]
Common Name English
6MNA
Code English
NAPROXEN IMPURITY I [EP IMPURITY]
Common Name English
2-(6-METHOXY-2-NAPHTHYL)ACETIC ACID
Systematic Name English
6-METHOXY-2-NAPHTHALENEACETIC ACID
Systematic Name English
2-NAPHTHALENEACETIC ACID, 6-METHOXY-
Systematic Name English
6-MNA
Common Name English
Code System Code Type Description
FDA UNII
9H7K3YOD7Q
Created by admin on Sat Dec 16 08:35:01 GMT 2023 , Edited by admin on Sat Dec 16 08:35:01 GMT 2023
PRIMARY
CHEBI
35628
Created by admin on Sat Dec 16 08:35:01 GMT 2023 , Edited by admin on Sat Dec 16 08:35:01 GMT 2023
PRIMARY
ECHA (EC/EINECS)
245-967-1
Created by admin on Sat Dec 16 08:35:01 GMT 2023 , Edited by admin on Sat Dec 16 08:35:01 GMT 2023
PRIMARY
EPA CompTox
DTXSID70178705
Created by admin on Sat Dec 16 08:35:01 GMT 2023 , Edited by admin on Sat Dec 16 08:35:01 GMT 2023
PRIMARY
PUBCHEM
32176
Created by admin on Sat Dec 16 08:35:01 GMT 2023 , Edited by admin on Sat Dec 16 08:35:01 GMT 2023
PRIMARY
CAS
23981-47-7
Created by admin on Sat Dec 16 08:35:01 GMT 2023 , Edited by admin on Sat Dec 16 08:35:01 GMT 2023
PRIMARY
Related Record Type Details
Structure of NABUMETONE
PARENT -> METABOLITE ACTIVE
Structure of NABUMETONE
PARENT -> METABOLITE
Related Record Type Details
Structure of NAPROXEN
PARENT -> IMPURITY
UNSPECIFIED
EP
Structure of NAPROXEN SODIUM
PARENT -> IMPURITY
UNSPECIFIED
EP
NIH
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