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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 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)
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
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
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