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Key Documents

UC305

Sigma-Aldrich

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:
Molecular Weight:
216.23
Beilstein:
8838512
MDL number:
UNSPSC Code:
12161501
PubChem Substance ID:
NACRES:
NA.77

form

solid

Quality Level

color

white

mp

182-183 °C

storage temp.

2-8°C

SMILES string

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

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

InChI key

XWJUDDGELKXYNO-QMMMGPOBSA-N

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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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Da-Fang Zhong et al.
Acta pharmacologica Sinica, 24(5), 442-447 (2003-05-13)
The metabolites of naproxen produced by Cunninghamella species were isolated and identified, and further to compare the similarities between microbial transformation and mammalian metabolism. Naproxen was transformed by three strains of Cunninghammella species (Cunninghamella blakeslesna AS 3.153, Cunninghamella echinulata AS
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
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
Charles N Falany et al.
British journal of clinical pharmacology, 60(6), 632-640 (2005-11-25)
Naproxen is a nonsteroidal anti-inflammatory drug widely used as an analgesic and anti-inflammatory agent. The conjugated forms of naproxen and O-DMN, its demethylated metabolite, account for 66-92% of naproxen found in human urine. In this study, O-DMN and structurally related

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