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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:
52079-10-4
Molecular Weight:
216.23
Beilstein:
8838512
MDL number:
MFCD00869765
UNSPSC Code:
12161501
PubChem Substance ID:
329827666
NACRES:
NA.77

form

solid

Quality Level

200

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
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H317,H400

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
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
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
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
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