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Merck
CN

UC305

O-Desmethylnaproxen

Synonym(s):

(S)-6-Hydroxy-α-methyl-2-naphthaleneacetic acid, d-2-(6-Hydroxy-2-naphthyl)proprionic acid

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About This Item

Empirical Formula (Hill Notation):
C13H12O3
CAS Number:
52079-10-4
Molecular Weight:
216.23
UNSPSC Code:
12161501
NACRES:
NA.77
PubChem Substance ID:
329827666
MDL number:
MFCD00869765
Beilstein/REAXYS Number:
8838512

Key Documents

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InChI

1S/C13H12O3/c1-8(13(15)16)9-2-3-11-7-12(14)5-4-10(11)6-9/h2-8,14H,1H3,(H,15,16)/t8-/m0/s1

SMILES string

C[C@H](C(O)=O)c1ccc2cc(O)ccc2c1

InChI key

XWJUDDGELKXYNO-QMMMGPOBSA-N

form

solid

color

white

mp

182-183 °C

storage temp.

2-8°C

Quality Level

200

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Application

O-Desmethylnaproxen can be used for assaying naproxen metabolites.

Biochem/physiol Actions

CYP2C9 metabolite of naproxen

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000240923
0000240923
0000097728
0000094817
0000097569

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P L Walker et al.
Annals of clinical biochemistry, 24 ( Pt 2), 177-181 (1987-03-01)
Interference by naproxen in the spectrophotometric assay for urinary 5-hydroxyindoleacetic acid has been investigated. Gas chromatography-mass spectrometry demonstrated that ingestion of naproxen was associated with the production of four urinary components, unchanged drug and three metabolites, the major one being
Stephanie Selke et al.
Journal of chromatography. A, 1217(3), 419-423 (2009-12-17)
O-desmethylnaproxen (2-(6-hydroxynaphthalen-2-yl)propanoic acid) was identified in 10 different water samples from Germany and Pakistan. In the Pakistan samples it was found in all samples, surface water and effluents, exhibiting estimated concentrations between 0.04 and 1.36 microg/L. In Germany it was
Kushari Bowalgaha et al.
British journal of clinical pharmacology, 60(4), 423-433 (2005-09-29)
To characterize the kinetics of S-naproxen ('naproxen') acyl glucuronidation and desmethylnaproxen acyl and phenolic glucuronidation by human liver microsomes and identify the human UGT isoform(s) catalysing these reactions. Naproxen and desmethylnaproxen glucuronidation were investigated using microsomes from six and five
T B Vree et al.
Biopharmaceutics & drug disposition, 14(6), 491-502 (1993-08-01)
The aim of this investigation was to assess the pharmacokinetics of naproxen in 10 human subjects after an oral dose of 500 mg using a direct HPLC analysis of the acyl glucuronide conjugates of naproxen and its metabolite O-desmethylnaproxen. The
H Yokoyama et al.
Human & experimental toxicology, 13(12), 831-838 (1994-12-01)
1. Rat liver microsomal suspension containing NADPH and MgCl2 was incubated at 37 degrees C with naproxen, a non-steroidal anti-inflammatory drug. Thiobarbituric acid reactive substances (TBA-RS), high molecular weight protein aggregates and fluorescent substances were formed in the microsomal suspension.
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