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PHR1040

Naproxen

Name: Naproxen
Brand: SIAL

Pharmaceutical Secondary Standard; Certified Reference Material

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Synonym(s):

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

Linear Formula:

CH₃OC₁₀H₆CH(CH₃)CO₂H

CAS Number:

22204-53-1

Molecular Weight:

230.26

Beilstein:

3591068

EC Number:

244-838-7

MDL number:

MFCD00010500

PubChem Substance ID:

329823070

NACRES:

NA.24

grade

certified reference material
pharmaceutical secondary standard

Quality Level

300

Agency

traceable to BP 435
traceable to Ph. Eur. N0250000
traceable to USP 1457301

API family

naproxen

CofA

current certificate can be downloaded

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

152-154 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-30°C

SMILES string

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

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

InChI key

CMWTZPSULFXXJA-VIFPVBQESA-N

Gene Information

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

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Related Categories

Analytical Reference Standards

Sigma-Aldrich

Certified Reference Materials

General description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Naproxen belongs to the class of arylacetic acids and is used as a non-steroidal anti-inflammatory drug (NSAID). It is useful for the management of pain, inflammation and stiffness. It is also used in the treatment of rheumatoid arthritis and other painful musculoskeletal disorders.

Application

Naproxen may be used as a pharmaceutical reference standard for the determination of the analyte in pharmaceutical formulations by high performance liquid chromatography (HPLC) technique.

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Biochem/physiol Actions

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

Analysis Note

These secondary standards offer multi-traceability to the USP, EP (PhEur) and BP primary standards, where they are available.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAA8968 in the slot below. This is an example certificate only and may not be the lot that you receive.

Recommended products

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

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1457312

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(S)-Naproxen ethyl ester, pharmaceutical impurity standard

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(S)-Naproxen methyl ester, pharmaceutical impurity standard

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(2S)-2-(5-Chloro-6-methoxynaphthalen-2-yl)propanoic acid, pharmaceutical impurity standard

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(2S)-2-(5-Bromo-6-methoxynaphthalen-2-yl)propanoic acid, pharmaceutical impurity standard

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2-Bromo-6-methoxynaphthalene, pharmaceutical impurity standard

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Pictograms

GHS07,GHS08,GHS09

Signal Word

Warning

Hazard Statements

H302 - H315 - H319 - H335 - H361fd - H411

Precautionary Statements

P202 - P273 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313

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 Code

11 - Combustible Solids

WGK

WGK 3

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Simultaneous determination of naproxen, ketoprofen and phenol red in samples from rat intestinal permeability studies: HPLC method development and validation

Zakeri-Milani P, et al.

Journal of Pharmaceutical and Biomedical Analysis, 39(3-4), 624-630 (2005)

High performance liquid chromatography with photo diode array for separation and analysis of naproxen and esomeprazole in presence of their chiral impurities: enantiomeric purity determination in tablets

Ragab MAA and Eman I

Journal of Chromatography A, 1497, 110-117 (2017)

Comparison of rofecoxib, celecoxib, and naproxen on renal function in elderly subjects receiving a normal-salt diet.

J I Schwartz et al.

Clinical pharmacology and therapeutics, 72(1), 50-61 (2002-08-02)

This study compared directly the renal effects of two selective cyclooxygenase (COX)-2 inhibitors (rofecoxib and celecoxib) with naproxen (dual COX-1/COX-2 inhibitor) and placebo in healthy elderly subjects on a sodium-replete diet. A total of 67 elderly subjects stabilized in the

Efficacy and safety of infliximab plus naproxen versus naproxen alone in patients with early, active axial spondyloarthritis: results from the double-blind, placebo-controlled INFAST study, Part 1.

J Sieper et al.

Annals of the rheumatic diseases, 73(1), 101-107 (2013-05-23)

To assess whether combination therapy with infliximab (IFX) plus nonsteroidal anti-inflammatory drugs (NSAIDs) is superior to NSAID monotherapy for reaching Assessment of SpondyloArthritis international Society (ASAS) partial remission in patients with early, active axial spondyloarthritis (SpA) who were naïve to

A hydrogen sulfide-releasing cyclooxygenase inhibitor markedly accelerates recovery from experimental spinal cord injury.

Michela Campolo et al.

FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 27(11), 4489-4499 (2013-08-01)

Spinal cord trauma causes loss of motor function that is in part due to the ensuing inflammatory response. Hydrogen sulfide (H2S) is a potent, endogenous anti-inflammatory and neuroprotective substance that has been explored for use in the design of novel

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