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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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P J Guelen et al.
International journal of clinical pharmacology, therapy, and toxicology, 26(4), 190-193 (1988-04-01)
After a rectal dose of 500 mg in a suppository, naproxen is 6-O-demethylated (20%) and glucuronidated (40%), the metabolites are subsequently excreted renally. The elimination half-life is 15.2 +/- 2.6 h. Ten out of 22 subjects show biphasic elimination kinetics
High-performance liquid chromatographic determination of 6-desmethylnaproxen sulfate in human plasma.
C H Kiang et al.
Journal of chromatography, 383(2), 449-455 (1986-12-19)
Hypoalbuminaemia and naproxen pharmacokinetics in a patient with rheumatoid arthritis.
F A Van den Ouweland et al.
Clinical pharmacokinetics, 11(6), 511-515 (1986-11-01)
Amitava Dasgupta et al.
American journal of clinical pathology, 133(6), 878-883 (2010-05-18)
A recent report indicated significant interference of naproxen with total bilirubin measurement when using the Jendrassik and Grof method. We explored the possibility of avoiding this interference by using a different method. We observed that naproxen has no effect on
T B Vree et al.
Journal of chromatography, 578(2), 239-249 (1992-07-24)
Naproxen is metabolized in humans by O-demethylation, and by acyl glucuronidation to the 1-O-glucuronide. Naproxen, its metabolite and the conjugates can be measured directly by gradient high-performance liquid chromatographic analysis without enzymic deglucuronidation. The glucuronide conjugates were isolated by preparative
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