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Naproxen

CAS# 22204-53-1

Naproxen

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Chemical structure

Naproxen

3D structure

Chemical Properties of Naproxen

Cas No. 22204-53-1 SDF Download SDF
PubChem ID 156391 Appearance Powder
Formula C14H14O3 M.Wt 230.3
Type of Compound N/A Storage Desiccate at -20°C
Synonyms (S)-Naproxen
Solubility DMSO : ≥ 100 mg/mL (434.29 mM)
H2O : 75 mg/mL (325.72 mM; Need ultrasonic and warming)
*"≥" means soluble, but saturation unknown.
Chemical Name (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
SMILES CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O
Standard InChIKey CMWTZPSULFXXJA-VIFPVBQESA-N
Standard InChI 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
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.

Protocol

Cell Assay [1]
BAEC are incubated for 30 min with Naproxen (0.1 ng/mL to 1 mg/mL). Arachidonic acid (30 μM) is then added, and the cells are incubated for a further 15 min at 37°C. The medium is then removed, and radioimmunoassay is used to measure the formation of 6-keto-PGF,a, PGE2, thromboxane B2, or PGF2a[1].

Animal Administration [2][3]
Rats[3] To measure the analgesic effects of naproxen in a carrageenaninduced model of monoarthritis, Male Sprague–Dawley rats (n=48, 217±28 g) are randomly divided into four groups of 12 by an internally developed computer program, allowing the blind performance of the behavioral experiment. To induce hyperalgesia by inflammation, animals in groups 1B, 1C, and 1D receive a 40-μL intra-articular injection of a saline solution containing 7.5 mg/mL carrageenan in the left hind limb under isoflurane anesthesia (time=−1 h). Animals in group 1A receive no injection. After 1 h (time=0) the animals in groups 1A, 1B, 1C, and 1D receive oral doses of naproxen in saline of 0, 0, 7.5 and 30 μmol/kg, respectively. The doses and time points of measurements are selected on the basis of simulations predicting measuring a full concentration-effect relationship within the time-span of the experiment[3]. Mice[2]Bleomycin (0.05 IU) is instilled intratracheally to C57BL/6 mice, which are then treated by micro-osmotic pump with vehicle, JNJ7777120 (40 mg/kg b.wt.), naproxen (21 mg/kg b.wt.), or a combination of both. Airway resistance to inflation, an index of lung stiffness, is assessed, and lung specimens are processed for inflammation, oxidative stress, and fibrosis markers[2].

References:
[1]. Mitchell JA, et al. Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proc Natl Acad Sci U S A. 1993 Dec 15;90(24):11693-7. [2]. Rosa AC, et al. Prevention of bleomycin-induced lung inflammation and fibrosis in mice by naproxen and JNJ7777120 treatment. J Pharmacol Exp Ther. 2014 Nov;351(2):308-16. [3]. Krekels EH, et al. Pharmacokinetic-pharmacodynamic modeling of the inhibitory effects of naproxen on the time-courses of inflammatory pain, fever, and the ex vivo synthesis of TXB2 and PGE2 in rats.

Naproxen Dilution Calculator

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Preparing Stock Solutions of Naproxen

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.3422 mL 21.7108 mL 43.4216 mL 86.8432 mL 108.5541 mL
5 mM 0.8684 mL 4.3422 mL 8.6843 mL 17.3686 mL 21.7108 mL
10 mM 0.4342 mL 2.1711 mL 4.3422 mL 8.6843 mL 10.8554 mL
50 mM 0.0868 mL 0.4342 mL 0.8684 mL 1.7369 mL 2.1711 mL
100 mM 0.0434 mL 0.2171 mL 0.4342 mL 0.8684 mL 1.0855 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

Naproxen is a COX-1 and COX-2 inhibitor with IC50s of 2.2 and 1.3 μg/mL, respectively in cell assay.

In Vitro:Naproxen etemesil is a lipophilic, non-acidic, inactive prodrug of naproxen that is hydrolysed to pharmacologically active Naproxen once absorbed. Naproxen is a well known nonsteroidal anti-inflammatory drug. Naproxen is approximately equipotent inhibitor of COX-1 and COX-2 in intact cells with IC50s of 2.2 μg/mL and 1.3 μg/mL, respectively[1].

In Vivo:Naproxen exerts an anti-inflammatory and antifibrotic effect in mouse model of bleomycin-induced lung fibrosis. Naproxen also downregulates TGF-β levels and Smad3/4 complex formation[2]. Naproxen is shown to inhibit the time-courses of pain, fever and PGE2 with similar potencies (IC50=27, 40, 13 μM)[3].

References:
[1]. Mitchell JA, et al. Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proc Natl Acad Sci U S A. 1993 Dec 15;90(24):11693-7. [2]. Rosa AC, et al. Prevention of bleomycin-induced lung inflammation and fibrosis in mice by naproxen and JNJ7777120 treatment. J Pharmacol Exp Ther. 2014 Nov;351(2):308-16. [3]. Krekels EH, et al. Pharmacokinetic-pharmacodynamic modeling of the inhibitory effects of naproxen on the time-courses of inflammatory pain, fever, and the ex vivo synthesis of TXB2 and PGE2 in rats.

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References on Naproxen

INTREPAD: A randomized trial of naproxen to slow progress of presymptomatic Alzheimer disease.[Pubmed:30952794]

Neurology. 2019 Apr 5. pii: WNL.0000000000007232.

OBJECTIVE: To evaluate the safety and efficacy of low-dose Naproxen for prevention of progression in presymptomatic Alzheimer disease (AD) among cognitively intact persons at risk. METHODS: Investigation of Naproxen Treatment Effects in Pre-symptomatic Alzheimer's Disease (INTREPAD), a 2-year double-masked pharmaco-prevention trial, enrolled 195 AD family history-positive elderly (mean age 63 years) participants screened carefully to exclude cognitive disorder (NCT-02702817). These were randomized 1:1 to Naproxen sodium 220 mg twice daily or placebo. Multimodal imaging, neurosensory, cognitive, and (in approximately 50%) CSF biomarker evaluations were performed at baseline, 3, 12, and 24 months. A modified intent-to-treat analysis considered 160 participants who remained on-treatment through their first follow-up examination. The primary outcome was rate of change in a multimodal composite presymptomatic Alzheimer Progression Score (APS). RESULTS: Naproxen-treated individuals showed a clear excess of adverse events. Among treatment groups combined, the APS increased by 0.102 points/year (SE 0.014; p < 10(-12)), but rate of change showed little difference by treatment assignment (0.019 points/year). The treatment-related rate ratio of 1.16 (95% confidence interval 0.64-1.96) suggested that Naproxen does not reduce the rate of APS progression by more than 36%. Secondary analyses revealed no notable treatment effects on individual CSF, cognitive, or neurosensory biomarker indicators of progressive presymptomatic AD. CONCLUSIONS: In cognitively intact individuals at risk, sustained treatment with Naproxen sodium 220 mg twice daily increases frequency of adverse health effects but does not reduce apparent progression of presymptomatic AD. CLASSIFICATION OF EVIDENCE: This study provides Class I evidence that, for people who are cognitively intact, low-dose Naproxen does not significantly reduce progression of a composite indicator of presymptomatic AD.

A systematic review and meta-analysis of naproxen for prevention heterotopic ossification after hip surgery.[Pubmed:30946309]

Medicine (Baltimore). 2019 Apr;98(14):e14607.

BACKGROUND: The aim of this study was to assess the efficacy of Naproxen in preventing heterotopic ossification (HO) after hip surgery (total hip arthroplasty [THA] and hip arthroscopy). METHODS: Using databases (PubMed, EMBASE, and Web of Science), we conducted an electronic, systematic search of randomized controlled trials (RCTs) comparing Naproxen versus placebo on HO after hip surgery. The risk ratio (RR) of the dichotomous data, weighted mean difference (WMD) of continuous data, and 95% confidence intervals (CIs) were calculated to assess the effects of Naproxen in patients with hip surgery. RESULTS: A total of 4 studies including 269 patients were analyzed. Risk of bias was relatively high in allocation concealment and blinding. Compared with control group, administration Naproxen was associated with a significantly reduction of the occurrence of HO at final follow-up after hip surgery (P < .05). What's more, Naproxen was associated with a reduction of the Brooker I and II HO (P < .05). However, there was no significant difference between the Brooker III HO between Naproxen and control groups (P > .05). Furthermore, there was no significant difference between the complications (P > .05) between Naproxen and control groups. CONCLUSION: Naproxen has a beneficial role in reducing the total occurrence of HO, Brooker I and II HO after hip surgery. However, conclusions are limited due to the lack of high-quality studies. More high quality studies may help in a more reliable therapy for HO.

Metal-Based Scaffolds of Schiff Bases Derived from Naproxen: Synthesis, Antibacterial Activities, and Molecular Docking Studies.[Pubmed:30934936]

Molecules. 2019 Mar 29;24(7). pii: molecules24071237.

We report here the synthesis, characterization, and antibacterial evaluation of transition metal complexes of Ni, Cu, Co, Mn, Zn, and Cd (6a(-)f), using a Schiff base ligand (5) derived from Naproxen (an anti-inflammatory drug) and 5-bromosalicylaldehyde by a series of reactions. The ligand and the synthesized complexes were characterized by elemental analysis, UV-Visible, FTIR, and XRD techniques. The ligand 5 behaves as a bidentate donor and coordinates with metals in square planar or tetrahedral fashion. In order to evaluate its bioactivity profile, we screened the Schiff base ligand and its metal complexes (6a(-)f) against different species of bacteria and the complexes were found to exhibit significant antibacterial activity. The complexes showed more potency against Bacillus subtilis as compared to the other species. Moreover, we modeled these complexes' binding affinity against COX1 protein using computational docking.

Electrochemical degradation of naproxen from water by anodic oxidation with multiwall carbon nanotubes glassy carbon electrode.[Pubmed:30924802]

Water Sci Technol. 2019 Feb;79(3):480-488.

Naproxen (NPX) degradation was investigated by anodic oxidation both at constant potential and by cyclic voltammetry, using this last technique for optimizing reaction conditions and catalyst properties. Three multiwall carbon nanotubes (MWCNTs)-promoted electrodes were used (MWCNT, MWCNT-COOH and MWCNT-NH2) and a two steps oxidation process was observed in all the cases. At the optimized conditions (volume of MWCNT = 15 muL), the influence of the scan rate indicates the diffusion-adsorption control of the process. Likewise, the kinetic study of NPX degradation at fix potential, considering two different stirring speeds (250 and 500 rpm), indicates that degradation rate increases with the stirring speed. After 20 h, NPX is degraded even an 82.5%, whereas the mineralization reaches almost 70%, as it was obtained from total organic carbon analysis. The pH effect was also analysed, in the range 5-11, observing a positive effect at low pH. Concerning the surface chemistry of the electrode, MWCNT-NH2, with the highest isoelectric point (4.70), is the most promising material due to the improved interactions with the reactant. From these observations, a pathway is proposed, which includes two steps of electrochemical oxidation followed by subsequent oxidation steps, until mineralization of the NPX, attributed mainly to active chlorine species and .OH.

Description

Naproxen 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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