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Naproxen Sodium

cyclooxygenase inhibitor CAS# 26159-34-2

Naproxen Sodium

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Quality Control of Naproxen Sodium

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Chemical structure

Naproxen Sodium

3D structure

Chemical Properties of Naproxen Sodium

Cas No. 26159-34-2 SDF Download SDF
PubChem ID 23681059 Appearance Powder
Formula C14H13NaO3 M.Wt 252.24
Type of Compound N/A Storage Desiccate at -20°C
Solubility H2O : 75 mg/mL (297.34 mM; Need ultrasonic and warming)
DMSO : 5 mg/mL (19.82 mM; Need ultrasonic)
Chemical Name sodium;(2S)-2-(6-methoxynaphthalen-2-yl)propanoate
SMILES CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)[O-].[Na+]
Standard InChIKey CDBRNDSHEYLDJV-FVGYRXGTSA-M
Standard InChI InChI=1S/C14H14O3.Na/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);/q;+1/p-1/t9-;/m0./s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Naproxen Sodium

DescriptionNon-selective cyclooxygenase (COX) inhibitor that displays anti-inflammatory, antipyretic and analgesic effects. Has a neuroprotective role against colchicine-induced cognitive impairment and oxidative stress.

Naproxen Sodium Dilution Calculator

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Naproxen Sodium Molarity Calculator

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Preparing Stock Solutions of Naproxen Sodium

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.9645 mL 19.8224 mL 39.6448 mL 79.2896 mL 99.112 mL
5 mM 0.7929 mL 3.9645 mL 7.929 mL 15.8579 mL 19.8224 mL
10 mM 0.3964 mL 1.9822 mL 3.9645 mL 7.929 mL 9.9112 mL
50 mM 0.0793 mL 0.3964 mL 0.7929 mL 1.5858 mL 1.9822 mL
100 mM 0.0396 mL 0.1982 mL 0.3964 mL 0.7929 mL 0.9911 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Naproxen Sodium

Naproxen sodium is a nonselective cyclooxygenase inhibitor [1], with an ex vivo IC50 value of 35.48 μmol/L to cyclooxygenase-1 (COX-1) inhibition regarding naproxen plasma levels, and an ex vivo IC50 value of 64.62 µmol/L to cyclooxygenase-2 (COX-2) regarding naproxen plasma levels [2].

COX enzymes showed to be important for satellite cell fusion, proliferation and differentiation. COX-2 inhibition alone produced decreased satellite cell proliferation. Inhibition of both COX-1 and COX-2 decreased the fusion and differentiation of satellite cell [1].

Treatment with naproxen (0.5-1.5 mM) or licofelone (100-150 µM) was applied. After 48 h, the evaluation of HCA-7 cell viability was determined with trypan blue exclusion assay. Naproxen significantly decreased HCA-7 cell viability with an IC50 value of 1.45 ± 0.07 mM, and licofelone with an IC50 value of 72 ± 3.6 µM [3].

In four volunteers, 220 mg naproxen sodium b.i.d. was applied for 7 days. After a single dose and at steady state, maximal inhibition was as follows: 79% and 85% (COX-2), 94% and 93% (COX-1). In 2 of 4 volunteers applied with a single-dose administration, a greater than 95% COX-1 inhibition was transiently found at the time of maximal plasma concentration. In 1 of 4 volunteers throughout the 12-hour dose interval, a greater than 95% COX-1 inhibition was transiently found at steady state [2].

Treatments with placebo (PL) for 3 months or naproxen sodium (Nxs) 550 mg twice each day by mouth was applied to forty women suffering from Menstrual Migraine (MM). In the next 3 months, in an open study, active drug was applied to all the women. Compared to PL, treatment with Nxs significantly reduced the number of days of headache, the headache duration and intensity, and the analgesic consumption [4].

References:
[1].  Mendias CL, Tatsumi R and Allen RE. Role of cyclooxygenase-1 and -2 in satellite cell proliferation, differentiation, and fusion. Muscle Nerve, 2004, 30(4):497-500.
[2].  Hinz B, Cheremina O, Besz D, et al. Impact of naproxen sodium at over-the-counter doses on cyclooxygenase isoforms in human volunteers. Int J Clin Pharmacol Ther, 2008, 46(4):180-6.
[3].  Sances G, Martignoni E, Fioroni L, et al. Naproxen sodium in menstrual migraine prophylaxis: a double-blind placebo controlled study. Headache, 1990, 30(11):705-9.
[4].  Tavolari S, Bonafè M, Marini M, et al. Licofelone, a dual COX/5-LOX inhibitor, induces apoptosis in HCA-7 colon cancer cells through the mitochondrial pathway independently from its ability to affect the arachidonic acid cascade. Carcinogenesis, 2008, 29(2):371-80.

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References on Naproxen Sodium

Development and Evaluation of Naproxen Sodium Gel Using Piper cubeba for Enhanced Transdermal Drug Delivery and Therapeutic Facilitation.[Pubmed:28056749]

Recent Pat Drug Deliv Formul. 2017;11(1):28-35.

BACKGROUND: The absorption of drug through skin avoids many side effects of oral route like gastric irritation, nausea, systemic toxicity etc and thus improves patient compliance. Naproxen Sodium (NPRS) is one of the potent NSAID agents. OBJECTIVE: The present study was aimed to develop and evaluate the gel formulation containing NPRS for transdermal drug delivery reducing the side effects and improving patient compliance. The patents on topical delivery of NSAIDS (US 9012402 B1, US 9072659 B2, US 20150258196 A1) and patents indicating use of herbal penetration enhancers (US 20100273746A1, WO 2005009510 A2, US 6004969 A) helped in selecting the drug, excipients. METHOD: Current protocol employs various extracts of Piper cubeba fruit to evaluate its role in absorption of NPRS. Various batches containing 1% NPRS and varying concentrations of synthetic permeation enhancers or the extracts were formulated in carbopol gel. Gel was evaluated for parameters like organoleptic parameters, pH, viscosity and spreadability. An ex-vivo percutaneous absorption of NPRS from gel was investigated and compared with best performing synthetic enhancer, transcutol P (TP). RESULT: The batch containing 2% n-hexane extract (NHE) of Piper cubeba showed higher permeation than TP and Chloroform (CE), Methanolic (ME) and aqueous (AE) extracts as well. It showed improved % cumulative release (85.09%) and flux (278.61mug/cm2.h), as compared to TP and other extracts. Histopathology indicated the formulation safer as compared to that with synthetic enhancer. CONCLUSION: It suggests P. cubeba as effective and safer tool for transdermal delivery and acts as therapeutic facilitator for naproxen. GC-MS analysis indicates lignans & terpenes in NHE to which this permeation enhancement activity may be attributed.

Synthesis and Formulation of Thermosensitive Drug Carrier for Temperature Triggered Delivery of Naproxen Sodium.[Pubmed:27827936]

Molecules. 2016 Nov 4;21(11). pii: molecules21111473.

Nanospheres and microspheres are known as a multipurpose compounds and are used in various branches of science. Recent controlled delivery systems for drugs are also based on poly-micro and nanospheres. In our study we describe an investigation of the influence of thermosensitive polymer N-isopropylacrylamide (NIPA) on the release of the drug Naproxen Sodium (NS) with a hydrogel hydroxypropyl methylcellulose (HPMC) base. The hydrodynamic diameter (DH) of the obtained polymer was measured by using dynamic light scattering (DLS) at a wavelength of 678 nm. Hydrogel formulations of NS were prepared in a specific way ex tempore. NS was sprinkled on the surface of a distilled water, then polymer soluted in water was added. Afterward, HPMC was affixed to the solution. Prepared samples were stored at room temperature for 24 h. Release tests showed that modification of thevcross-linker type influenced the properties of synthesized polymeric particles. The NIPA derivatives obtained via surfactant free precipitation polymerization (SFPP) may be formulated as hydrogel preparations using HPMC. The obtained formulations presented varied half-release times, depending on the type of applied NIPA derivatives in hydrogel formulations. At 18 degrees C, the release rates were lower comparing to the reference HPMC hydrogel, whereas at 42 degrees C, the release rates were significantly higher. The synthesized thermosensitive polymers enabled temperature-triggered release of NS.

The effect of hydroxyapatite in biopolymer-based scaffolds on release of naproxen sodium.[Pubmed:27449255]

J Biomed Mater Res A. 2016 Dec;104(12):2992-3003.

A scaffold capable of controlling drug release is highly desirable for bone tissue engineering. The objective of this study was to develop and characterize a highly porous biodegradable scaffold and evaluate the kinetic release behavior for the application of anti-inflammatory drug delivery. Porous scaffolds consisting of chitosan, poly(acrylic acid), and nano-hydroxyapatite were prepared using the freeze-drying method. The nanocomposite scaffolds were characterized for structure, pore size, porosity, and mechanical properties. The nanocomposite scaffolds were tested and characterized using Fourier transform infrared (FTIR) spectroscopy, scanning electron microscopy (SEM), energy-dispersive analysis of X-ray (EDS), X-ray diffraction (XRD) analysis, and tensile test instrument. The results showed that the pores of the scaffolds were interconnected, and their sizes ranged from 145 microm to 213 mum. The mechanical properties were found close to those of trabecular bone of the same density. The ability of the scaffolds to deliver Naproxen Sodium as a model drug in vitro was investigated. The release profile of Naproxen Sodium was measured in a phosphate-buffered saline solution by a ultra-violet spectrophotometer that was controlled by the Fickian diffusion mechanism. These results indicated that the chitosan-graft-poly(acrylic acid)/nano-hydroxyapatite scaffold may be a promising biomedical scaffold for clinical use in bone tissue engineering with a potential for drug delivery. (c) 2016 Wiley Periodicals, Inc. J Biomed Mater Res Part A: 104A: 2992-3003, 2016.

Naproxen Sodium for Pain Control With Intrauterine Device Insertion: A Randomized Controlled Trial.[Pubmed:27824753]

Obstet Gynecol. 2016 Dec;128(6):1306-1313.

OBJECTIVE: To evaluate whether 550 mg oral Naproxen Sodium given 1 hour before intrauterine device (IUD) insertion is effective for pain relief as compared with placebo. METHODS: This was a randomized, double-blind, placebo-controlled trial. The primary outcome was pain with IUD insertion measured on a 100-mm visual analog scale (VAS). Our sample size was calculated to detect a 15-mm difference in VAS scores with 80% power (alpha=0.05). Secondary outcomes included pain with tenaculum placement, uterine sounding, and 5 and 15 minutes postinsertion. RESULTS: A total of 118 women were enrolled and analyzed (58 in the Naproxen Sodium arm, 60 in the placebo arm, 97% nulliparous) between May 11, 2015, and March 25, 2016. There were no differences in baseline demographics or reproductive characteristics between arms. There were no differences in median VAS pain scores for the primary outcome of pain with IUD insertion between the Naproxen Sodium arm compared with the placebo arm (69 compared with 66 mm, P=.89). There were no differences in the secondary outcomes of median VAS pain scores with tenaculum placement (37 compared with 32 mm, P=.97) or uterine sounding (60 compared with 58 mm, P=.66). However, median pain scores postprocedure were lower in the naproxen arm as compared with the placebo arm: 17 compared with 26 mm (P=.01) at 5 minutes and 13 compared with 24 mm (P=.01) at 15 minutes postinsertion. CONCLUSION: Oral Naproxen Sodium does not reduce pain with IUD insertion but does reduce pain after insertion and should be considered as a premedication. CLINICAL TRIAL REGISTRATION: ClinicalTrials.gov, http://clinicaltrials.gov, NCT02388191.

Protective effect of naproxen (non-selective COX-inhibitor) or rofecoxib (selective COX-2 inhibitor) on immobilization stress-induced behavioral and biochemical alterations in mice.[Pubmed:16522321]

Eur J Pharmacol. 2006 Mar 27;535(1-3):192-8.

Chronic stress precipitates many neuropsychiatric disorders and alters the various oxidative stress parameters in brain. Cyclooxygenase (COX) is reported to play an important role in pathogenesis of various neurodegenerative disorders including stroke and seizures. In the present study, we examined the effect of naproxen (non-selective COX-inhibitor having much potency towards COX-I isoform) or rofecoxib (a selective COX-2 inhibitor) in subchronic immobilization stress. Mice were subjected to immobilized stress for 6 h daily for a period of seven days. Naproxen (7 mg/kg, i.p.) or rofecoxib (2 mg/kg, i.p.) was administered daily for 7 days before challenging them to immobilization stress. Behavioral analysis revealed the hyperlocomotor activity and increased anxiety response. Subchronic stress decreased percent retention of memory and also caused hyperalgesia in mice. Biochemical analysis revealed that chronic immobilization stress significantly increased lipid peroxidation and nitrite levels and decreased the reduced glutathione and adrenal ascorbic acid levels. Chronic treatment with naproxen or rofecoxib significantly attenuated the immobilization stress-induced behavioral and biochemical alterations. These results suggested that the use of COX-inhibitors (naproxen or rofecoxib) could be a useful neuroprotective strategy in the treatment of stress.

Differential effects of cyclooxygenase inhibitors on intracerebroventricular colchicine-induced dysfunction and oxidative stress in rats.[Pubmed:17027965]

Eur J Pharmacol. 2006 Dec 3;551(1-3):58-66.

Alzheimer's disease is a progressive neurological and psychiatric disorder. Oxidative stress and neuroinflammation have been implicated in pathophysiology of Alzheimer's disease. Inflammatory cells, such as astrocytes and microglia, are activated in areas of the brain affected by amyloid plaques and inflammatory mediators including cytokines, chemokines, prostaglandins, oxygen free radicals and reactive nitrogen species may have a crucial role in Alzheimer's disease pathogenesis. Central administration of colchicine, a microtubule-disrupting agent, causes loss of cholinergic neurons and cognitive dysfunction that is associated with excessive free radical generation. The present study was aimed to evaluate the effects of cyclooxygenase inhibitors against colchicine-induced cognitive dysfunction and oxidative stress in rats. Following intracerebroventricular (i.c.v.) administration of colchicine (15 microg/5 microl), rats exhibited poor retention of memory in Morris water maze and elevated plus maze task paradigms and oxidative stress in rats. Chronic treatment with naproxen (per se; 20 and 40 mg/kg, p.o.) or valdecoxib (per se; 5 and 10 mg/kg, p.o.) daily respectively for a period of 25 days beginning 4 days prior to colchicine injection significantly improved colchicine-induced cognitive impairment. Intracerebroventricular colchicine injection resulted in free radical generation characterized by alterations in oxidative stress markers with a significant increase in malondialdehyde and nitrite levels and depletion of reduced glutathione levels in the brains of rats. It also caused a decrease in acetylcholinesterase activity. Besides, improving cognitive dysfunction, chronic administration of cyclooxygenase inhibitors (naproxen and valdecoxib) significantly reduced elevated malondialdehyde, nitrite levels and restored reduced glutathione levels and acetylcholinesterase activity. The results of the present study indicated that naproxen (per se; 20 and 40 mg/kg, p.o.) or valdecoxib (per se; 5 and 10 mg/kg, p.o.) treatment has a neuroprotective role against colchicine-induced cognitive impairment and associated oxidative stress. The present findings further support the potential use of cyclooxygenase inhibitors in treatment of neurodegenerative diseases such as Alzheimer's disease.

Description

Naproxen sodium is a COX-1 and COX-2 inhibitor with IC50s of 8.72 and 5.15 μM, respectively in cell assay.

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