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Merck

1457301

USP

Naproxen

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

(S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid

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About This Item

Linear Formula:
CH3OC10H6CH(CH3)CO2H
CAS Number:
22204-53-1
Molecular Weight:
230.26
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329750529
MDL number:
MFCD00010500
Beilstein/REAXYS Number:
3591068

Product Name

Naproxen, United States Pharmacopeia (USP) Reference Standard

InChI

1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1

SMILES string

COc1ccc2cc(ccc2c1)[C@H](C)C(O)=O

InChI key

CMWTZPSULFXXJA-VIFPVBQESA-N

grade

pharmaceutical primary standard

API family

naproxen

manufacturer/tradename

USP

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

152-154 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

Gene Information

human ... PTGS1(5742), PTGS2(5743)

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Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Application

Naproxen USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Dexamethasone Compounded Oral Suspension
  • Naproxen
  • Naproxen Compounded Oral Suspension
  • Naproxen Delayed-Release Tablets
  • Naproxen Oral Suspension
  • Naproxen Tablets
  • Terazosin Tablets

Biochem/physiol Actions

Non-selective cyclooxygenase (COX-1 and COX-2) inhibitor.

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Other Notes

Sales restrictions may apply.

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

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Marta L Capone et al.
Journal of the American College of Cardiology, 45(8), 1295-1301 (2005-04-20)
We investigated the occurrence of pharmacodynamic interaction between low-dose aspirin and naproxen. The uncertainty of cardioprotection by naproxen has encouraged its combination with aspirin in patients with arthritis and cardiovascular disease. The incubation of washed platelets with naproxen for 5
Christopher Derry et al.
The Cochrane database of systematic reviews, (1)(1), CD004234-CD004234 (2009-01-23)
Naproxen, a non-steroidal anti-inflammatory drug, is used to treat various painful conditions including postoperative pain, and is often administered as the sodium salt to improve its solubility. This review updates a 2004 Cochrane review showing that naproxen sodium 550 mg
Chuthamanee C Suthisisang et al.
Headache, 50(5), 808-818 (2010-03-20)
To assess the efficacy and safety of naproxen sodium in the treatment of acute migraine attacks. Non-steroidal anti-inflammatory drugs including naproxen sodium have been used in treating migraine attack. A number of clinical trials of naproxen sodium in migraine have
Larisa Kovacevic et al.
Pediatric nephrology (Berlin, Germany), 18(8), 826-829 (2003-05-30)
A 17-year-old healthy girl was admitted to our hospital with diffuse abdominal pain and decreased oral intake of about 11 days duration. About a week prior to admission, she had taken naproxen, 250 mg four times a day for 4
Tarjinder Sahota et al.
Toxicology and applied pharmacology, 278(3), 209-219 (2014-03-29)
The assessment of safety in traditional toxicology protocols relies on evidence arising from observed adverse events (AEs) in animals and on establishing their correlation with different measures of drug exposure (e.g., Cmax and AUC). Such correlations, however, ignore the role
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