| Size | Price | Stock | Qty |
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| 100mg |
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| 500mg |
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| 1g |
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| Other Sizes |
| Targets |
(S)-Naproxen targets cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) enzymes, which are responsible for the production of prostaglandins. Prostaglandins are lipid mediators that play key roles in inflammation, pain, and fever. By inhibiting COX enzymes, naproxen reduces the production of prostaglandins, leading to decreased inflammation, pain relief, and fever reduction. Naproxen is a non-selective COX inhibitor, meaning it inhibits both COX-1 and COX-2. COX-1 is constitutively expressed and is involved in maintaining gastric mucosal integrity and platelet function, while COX-2 is induced during inflammation. The inhibition of COX-1 is responsible for the gastrointestinal side effects associated with NSAIDs. (S)-Naproxen is the active enantiomer, with the (R)-enantiomer being significantly less active. The compound's analgesic, anti-inflammatory, and antipyretic effects are mediated through COX inhibition.
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| ln Vitro |
In vitro, (S)-Naproxen inhibits COX-1 and COX-2 enzyme activity, reducing the production of prostaglandins. The compound has been shown to inhibit prostaglandin synthesis in various cell types including macrophages, endothelial cells, and fibroblasts. Naproxen's anti-inflammatory effects have been demonstrated in vitro by measuring the production of inflammatory mediators such as prostaglandin E2 (PGE2) and other cytokines. The compound also exhibits antioxidant properties, scavenging free radicals and reducing oxidative stress. Naproxen has been shown to modulate various signaling pathways involved in inflammation and cell survival. The compound's effects are concentration-dependent, with higher concentrations leading to greater COX inhibition. In vitro studies have also investigated naproxen's effects on cell proliferation and apoptosis in various cell lines.
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| ln Vivo |
In vivo, (S)-Naproxen has been extensively studied for its analgesic, anti-inflammatory, and antipyretic effects. The compound is effective in various animal models of pain and inflammation, including the carrageenan-induced paw edema model, the adjuvant-induced arthritis model, and various pain models. Naproxen's effects are dose-dependent, with higher doses providing greater pain relief and anti-inflammatory effects. The compound is rapidly absorbed after oral administration and has a long half-life, allowing for twice-daily dosing. Naproxen is widely used clinically for the treatment of various conditions including rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, gout, and acute pain. The compound is available as an over-the-counter and prescription medication. Naproxen's clinical efficacy and safety profile are well established.
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| Enzyme Assay |
In vitro enzyme assays for (S)-Naproxen typically involve measuring the inhibition of COX-1 and COX-2 enzyme activity. The compound is dissolved in appropriate solvents such as DMSO or ethanol and diluted in assay buffer at concentrations ranging from 0.1-100 μM. The enzyme is incubated with arachidonic acid substrate and varying concentrations of the compound. The production of prostaglandins is measured using ELISA, radioimmunoassay, or HPLC. IC50 values are calculated by plotting the percentage of inhibition against the compound concentration. Naproxen has IC50 values of approximately 2-10 μM for COX-1 and COX-2, with some selectivity for COX-1. The compound's inhibitory activity is concentration-dependent. For receptor binding studies, competitive binding assays can be employed to determine the binding affinity of naproxen to COX enzymes.
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| Cell Assay |
In vitro cell-based assays using (S)-Naproxen are conducted in various cell lines including macrophages, fibroblasts, and cancer cells. Cells are seeded in multi-well plates and treated with naproxen at concentrations ranging from 1-100 μM for 24-72 hours. Inflammatory cytokine production is measured by ELISA or qPCR. Prostaglandin production is measured by ELISA. Cell viability is assessed using MTT or CCK-8 assays. For mechanistic studies, cells are harvested for Western blot analysis to measure the expression of proteins involved in inflammation and signaling pathways. The compound is typically dissolved in DMSO or ethanol and diluted in cell culture medium, with the final solvent concentration kept below 0.1%. The compound's effects are concentration-dependent.
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| Animal Protocol |
In vivo animal experiments with (S)-Naproxen are conducted in various pain and inflammation models. The compound is typically administered orally, intraperitoneally, or subcutaneously at doses ranging from 1-50 mg/kg depending on the study. In pain models, naproxen is administered before or after pain induction, and pain behavior is assessed using various tests including the hot plate test, tail flick test, and von Frey test. In inflammation models, naproxen is administered before or after inflammation induction, and inflammatory markers are measured in tissues and serum. The compound's analgesic and anti-inflammatory effects are dose-dependent. Tissue samples are collected for histopathological examination and biochemical analysis. The compound is formulated in appropriate vehicles such as saline, carboxymethylcellulose, or PEG for administration.
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| ADME/Pharmacokinetics |
(S)-Naproxen has a molecular weight of approximately 230.26 g/mol and the formula C14H14O3. The compound is a white to off-white crystalline powder that is practically insoluble in water but soluble in organic solvents. For long-term storage, the compound is kept at room temperature in a dry place, protected from light. The compound's pharmacokinetic properties are well established. After oral administration, naproxen is rapidly and completely absorbed from the gastrointestinal tract. The compound is highly protein-bound (>99%) and has a volume of distribution of approximately 0.16 L/kg. Naproxen is metabolized in the liver by CYP2C9 and other enzymes, and is excreted primarily in urine. The compound's half-life in plasma is approximately 12-17 hours in humans. The compound's stability in solution should be assessed for specific applications.
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| Toxicity/Toxicokinetics |
(S)-Naproxen has been extensively studied for its toxicity. The compound is generally well-tolerated at therapeutic doses (250-500 mg twice daily). Common side effects include gastrointestinal upset, nausea, and headache. More serious side effects include gastrointestinal bleeding, ulceration, and perforation, which are related to COX-1 inhibition. Naproxen can also cause cardiovascular and renal effects. The compound is contraindicated in patients with a history of NSAID hypersensitivity, active gastrointestinal bleeding, or severe renal impairment. The compound's toxicity is dose-dependent, and the therapeutic window should be carefully considered for specific applications. The compound is available as an over-the-counter and prescription medication. Safety data sheets recommend standard handling procedures for pharmaceutical compounds.
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| References |
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| Additional Infomation |
(2R)-2-(6-methoxy-2-naphthyl)propionic acid is a member of the naphthalene family of compounds.
(S)-Naproxen (CAS 23979-41-1), also known as l-Naproxen, is the active enantiomer of the non-steroidal anti-inflammatory drug (NSAID) naproxen. Naproxen is widely used for the treatment of pain, inflammation, and fever. The compound has the molecular formula C14H14O3 and a molecular weight of approximately 230.26 g/mol. (S)-Naproxen is the pharmacologically active form, while the (R)-enantiomer is less active. Naproxen works by inhibiting cyclooxygenase (COX) enzymes, reducing the production of prostaglandins. The compound is available as an over-the-counter and prescription medication for various conditions including arthritis, gout, menstrual cramps, and musculoskeletal pain. The compound is a white to off-white crystalline powder that is practically insoluble in water but soluble in organic solvents. It is typically stored at room temperature and protected from light. Naproxen's clinical efficacy and safety profile are well established. |
| Molecular Formula |
C14H14O3
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|---|---|
| Molecular Weight |
230.2592
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| Exact Mass |
230.094
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| CAS # |
23979-41-1
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| Related CAS # |
(±)-Naproxen; 23981-80-8; Naproxen; 22204-53-1; Naproxen sodium; 26159-34-2; l-Naproxen; 23979-41-1
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| PubChem CID |
169118
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
403.9±20.0 °C at 760 mmHg
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| Melting Point |
156-158ºC(lit.)
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| Flash Point |
154.5±15.3 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.609
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| LogP |
3
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
17
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| Complexity |
277
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O(C([H])([H])[H])C1C([H])=C([H])C2C([H])=C(C([H])=C([H])C=2C=1[H])[C@]([H])(C(=O)O[H])C([H])([H])[H]
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| InChi Key |
CMWTZPSULFXXJA-SECBINFHSA-N
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| InChi Code |
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-/m1/s1
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| Chemical Name |
(2R)-2-(6-methoxynaphthalen-2-yl)propanoic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: ~100 mg/mL (~434.3 mM; with ultrasonication)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5 mg/mL (21.71 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), Clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (50.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 5 mg/mL (21.71 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), Clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (50.0 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.3429 mL | 21.7146 mL | 43.4292 mL | |
| 5 mM | 0.8686 mL | 4.3429 mL | 8.6858 mL | |
| 10 mM | 0.4343 mL | 2.1715 mL | 4.3429 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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