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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
134361
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
8228
 64.0 µM [IC50]
Prostaglandin G/H synthase 2
47
Target ID: P35354
Gene ID: 5743.0
Gene Symbol: PTGS2
Target Organism: Homo sapiens (Human)
Inhibitor
8228
 93.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
2, 4-diamino-6- hydroxy pyrimidine inhibits NSAIDs induced nitrosyl-complex EPR signals and ulcer in rat jejunum.
2002 Apr 18
Photosensitizing properties of 6-methoxy-2-naphthylacetic acid, the major metabolite of the phototoxic non-steroidal anti-inflammatory and analgesic drug nabumetone.
2005 Aug
Theoretical study of the phototoxicity of naproxen and the active form of nabumetone.
2008 Oct 30
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 Thu Jul 06 14:01:48 UTC 2023
Edited
by admin
on Thu Jul 06 14:01:48 UTC 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 Thu Jul 06 14:01:48 UTC 2023 , Edited by admin on Thu Jul 06 14:01:48 UTC 2023
PRIMARY
CHEBI
35628
Created by admin on Thu Jul 06 14:01:48 UTC 2023 , Edited by admin on Thu Jul 06 14:01:48 UTC 2023
PRIMARY
ECHA (EC/EINECS)
245-967-1
Created by admin on Thu Jul 06 14:01:48 UTC 2023 , Edited by admin on Thu Jul 06 14:01:48 UTC 2023
PRIMARY
EPA CompTox
DTXSID70178705
Created by admin on Thu Jul 06 14:01:48 UTC 2023 , Edited by admin on Thu Jul 06 14:01:48 UTC 2023
PRIMARY
PUBCHEM
32176
Created by admin on Thu Jul 06 14:01:48 UTC 2023 , Edited by admin on Thu Jul 06 14:01:48 UTC 2023
PRIMARY
CAS
23981-47-7
Created by admin on Thu Jul 06 14:01:48 UTC 2023 , Edited by admin on Thu Jul 06 14:01:48 UTC 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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