- Enantioselective Copper-Catalyzed Methylboration of Alkenes. [Journal Article]
- OLOrg Lett 2018 Feb 20
- An enantioselective Cu-catalyzed borylative cross-coupling reaction of alkenes, bis(pinacolato)diboron (B2(pin)2), and methyl iodide is reported. Alkenes including styrenes, β-substituted styrenes, a...
An enantioselective Cu-catalyzed borylative cross-coupling reaction of alkenes, bis(pinacolato)diboron (B2(pin)2), and methyl iodide is reported. Alkenes including styrenes, β-substituted styrenes, and challenging aliphatic olefins were smoothly transferred to the desired methylboration products with excellent diastereoselectivities (dr up to >99:1) and enantioselectivities (er up to 99:1). The utility of this process was demonstrated by the synthesis of naproxen and formal synthesis of two natural products.
- Degradation of anti-inflammatory drugs in municipal wastewater by heterogeneous photocatalysis and electro-Fenton process. [Journal Article]
- ETEnviron Technol 2018 Feb 19; :1-35
- Non-steroidal anti-inflammatory drugs (NSAID) are compounds frequently found in municipal wastewater and their degradation by conventional wastewater treatment plants (WWTP) is generally incomplete. ...
Non-steroidal anti-inflammatory drugs (NSAID) are compounds frequently found in municipal wastewater and their degradation by conventional wastewater treatment plants (WWTP) is generally incomplete. This study compared the efficiency of two advanced oxidation processes, namely heterogeneous photocatalysis (HP) and electro-Fenton (EF), in the degradation of a mixture of common NSAID (diclofenac, ibuprofen and naproxen) dissolved in either deionized water or effluent from a WWTP. Both processes were effective in degrading the NSAID mixture and the trend of degradation was as follows, diclofenac>naproxen>ibuprofen. EF with a current density of 40 mA cm-2and 0.3 mmol Fe2+L-1, was the most efficient process to mineralize the organic compounds, achieving up to 92% TOC removal in deionized water and 90% in the WWTP effluent after 3 h of reaction. HP with 1.4 g TiO2L-1at pH 7 under sunlight, produced 85% TOC removal in deionized water and 39% in WWTP effluent also after 3 h treatment. The lower TOC removal efficiency shown by HP with the WWTP effluent was attributed mainly to the scavenging of reactive species by background organic matter in the wastewater. On the contrary, inorganic ions in the wastewater may produce oxidazing species during the EF process, which contributes to a higher degradation efficiency. EF is a promising option for the treatment of anti-inflammatory pharmaceuticals in municipal WWTP at competitive electrical energy efficiencies.
- Self-Assembly of Binuclear Cu(II)-Histidine Complex for Absolute Configuration and Enantiomeric Excess Determination of Naproxen by Tandem Mass Spectrometry. [Journal Article]
- ACAnal Chem 2018 Feb 17
- Naproxen is one of the most consumed non-steroidal anti-inflammatory drugs and marketed as S-naproxen since R-naproxen is hepatotoxic. In this study, chiral recognition of naproxen has been investiga...
Naproxen is one of the most consumed non-steroidal anti-inflammatory drugs and marketed as S-naproxen since R-naproxen is hepatotoxic. In this study, chiral recognition of naproxen has been investigated by tandem mass spectrometry (MS/MS). Among all diastereomeric complexes formed between naproxen and the examined chiral selectors, including cyclodextrins (α/β/γ-CD), modified phenylalanines (N-acetyl-phenylalanine, N-t-butoxycarbonyl-phenylalanine, N-9-fluorenylmethyloxycarbonyl-phenylalanine), amino acids (Trp, Phe, Tyr, His), glucose, tartaric acid and vancomycin, a novel binuclear metal bound diastereomeric complexes [(M(II))2(S/R-Naproxen)(L-His)2-3H]+(M = Cu, Ni or Co with Cu being the best) could allow effective identification of the absolute configuration of naproxen and determination of its enantiomeric excess (ee) through MS/MS analysis. The key candidate structure of [(Cu(II))2(S/R-Naproxen)(L-His)2-3H]+has been revealed by means of collision-induced dissociation, ion mobility mass spectrometry and density functional theory calculations, indicating an interesting and unusual self-assembly compact geometry with the two Cu(II) ions bridged closely together (Cu-Cu distance is 3.04 Å) by the carboxylate groups of the two histidines. It was shown that the difference in dissociation efficiency between the two diastereomers was attributed to the interaction between the NH2 bond of the amino group of one histidine and the naphthyl ring of naproxen. The present report is the first to observe and characterize the complex of (Cu(II))2(His)2with aromatic acid, which could contribute to the chiral recognition of other chiral aromatic acids, design of catalysts based on binuclear copper bound complex, as well as the better understanding of metal ion complexation by His or His-containing ligands.
- Visible Light Degradation of Naproxen by Enhanced Photocatalytic Activity of NiO and NiS, Scavenger Study and Focus on Catalyst Support and Magnetization. [Journal Article]
- PPPhotochem Photobiol 2018 Feb 14
- This research was aimed to prepare a magnetically photocatalyst enabling to degrade pharmaceutical wastewater and detoxification of pollutant such as naproxen, by visible light irradiation. The nano-...
This research was aimed to prepare a magnetically photocatalyst enabling to degrade pharmaceutical wastewater and detoxification of pollutant such as naproxen, by visible light irradiation. The nano-sized NiS and NiO photocatalysts exhibit higher reactivity than their micro-sized counterparts but separation of the used photocatalyst from the degradation solution is hard and imperfect. To remove this difficulty, magnetic polypyrrole core-shell (Fe3O4@PPY) was synthesized and employed as catalyst support. The magnetization property of the synthesized photocatalysts measured by VSM technique indicated that the photocatalysts were sufficiently magnetized to be readily separated from degradation solution by use of external magnetic field. The DRS study showed that the band gap of the photocatalysts shifted to lower energy after immobilization on the support materials leading to higher degradation efficiency. The optimal efficiency was obtained with the catalysts loaded with 50% of NiO and 50% of NiS. The augmenting effect of H2O2and the inhibition influence of some organic and inorganic compounds on the degradation process were studied. Regeneration of the used photocatalyst was performed by heat treatment and the catalyst treated at 400°C retained most of its initial capacity. The degradation capacity was kinetically fast and the equilibrium was attained within 30 min. This article is protected by copyright. All rights reserved.
- In Hospitalized Patients with Influenza and an Infiltrate, Adding Clarithromycin and Naproxen to Oseltamivir Improves Outcomes. [Journal Article]
- AFAm Fam Physician 2017 Dec 15; 96(12):Online
- Comparative Effectiveness of Oral Pharmacologic Interventions for Knee Osteoarthritis: A Network Meta-analysis. [Journal Article]
- MRMod Rheumatol 2018 Feb 12; :1-19
- CONCLUSIONS: In the overall analysis, etoricoxib, celecoxib, and aceclofenac had the highest rankings for improving WOMAC pain. The ability to improve knee OA symptoms may differ depending on baseline pain and radiologic features.
- Cardiorenal Safety of OTC Analgesics. [Journal Article]
- JCJ Cardiovasc Pharmacol Ther 2018; 23(2):103-118
- Over-the-counter analgesics are used globally for the relief of acute pain. Although effective, these agents can be associated with adverse effects that may limit their use in some people. In the ear...
Over-the-counter analgesics are used globally for the relief of acute pain. Although effective, these agents can be associated with adverse effects that may limit their use in some people. In the early 2000s, observations from clinical trials of prescription-strength and supratherapeutic doses of nonselective and cyclooxygenase-2-selective nonsteroidal anti-inflammatory drugs (NSAIDs) raised safety concerns regarding the risk of cardiovascular adverse effects with the use of these medications. Subsequently, the US Food and Drug Administration mandated additional study of the cardiovascular safety of NSAIDs for a more comprehensive understanding of their risk. As these data were being collected, and based on a comprehensive review of prescription data and the recommendations of the US Food and Drug Administration Advisory Committee, the warning labels of over-the-counter NSAIDs were updated to emphasize the potential cardiovascular risks of these agents. The recently reported "Prospective Randomized Evaluation of Celecoxib Integrated Safety versus Ibuprofen or Naproxen" (PRECISION) trial, in which participants with osteoarthritis or rheumatoid arthritis and underlying cardiovascular risk factors were treated with prescription-strength celecoxib, ibuprofen, or naproxen, revealed similar rates of cardiovascular events (death from cardiovascular causes including hemorrhagic death, nonfatal myocardial infarction, or nonfatal stroke) among the 3 treatment groups. Although informative, the cardiovascular safety findings derived from PRECISION cannot be extrapolated to the safety of the over-the-counter pain relievers ibuprofen and naproxen, given that the doses used were higher (mean [standard deviation]: ibuprofen, 2045  mg; naproxen, 852  mg) and the durations of use longer (∼20 months) than recommended with over-the-counter use of NSAIDs, which for ibuprofen is up to 10 days. This review discusses the cardiorenal safety of the most commonly used over-the-counter analgesics, ibuprofen, naproxen, and acetaminophen. Available data suggest that there is little cardiovascular risk when over-the-counter formulations of these agents are used as directed in their labels.
- Application of Polymerization Activator in the Course of Synthesis of N-Isopropylacrylamide Derivatives for Thermally Triggered Release of Naproxen Sodium. [Journal Article]
- MMaterials (Basel) 2018 Feb 08; 11(2)
- Poly-N-isopropylacrylamide (polyNIPA) is an extensively studied polymer in the field of controlled drug delivery. PolyNIPA contains carbonyl and amide groups along a hydrophobic chain. In an aqueous ...
Poly-N-isopropylacrylamide (polyNIPA) is an extensively studied polymer in the field of controlled drug delivery. PolyNIPA contains carbonyl and amide groups along a hydrophobic chain. In an aqueous environment, crosslinked polyNIPA forms a gel characterized by a reversible volume phase transition temperature (VPTT), in response to changes in the external environment excited by the temperature factor. NIPA-based polymers were synthesized by a surfactant-free precipitation polymerization (SFPP) method at a temperature of 70 °C using the free radical initiator potassium persulfate (KPS) and at 35 °C using redox initiator system KPS with N,N,N',N'-tetramethylethylenediamine (TEMED). The synthesized products were evaluated via dynamic light scattering (DLS), nuclear magnetic resonance (NMR) and Fourier-transform infrared spectroscopy (FTIR). The chemical structure, molecular mass, and hydrodynamic diameter of obtained particles, as well as the effects of synthesized polymers on the release of the active substance, naproxen sodium (NS), from hydroxypropyl methyl cellulose (HPMC)-based hydrogels were assessed. The use of the TEMED activator affected the particle size, as well as the release kinetics of NS. The insertion of TEMED into reactant mixtures may be applied to modify the release kinetics of NS from hydrogel preparations.
- Gastrointestinal safety and tolerability of oral non-aspirin over-the-counter analgesics. [Journal Article]
- PMPostgrad Med 2018 Feb 08; :1-12
- Over-the-counter (OTC) analgesics are routinely used worldwide for self-management of various painful conditions. Despite this, there has been little in-depth review of the safety of non-aspirin anal...
Over-the-counter (OTC) analgesics are routinely used worldwide for self-management of various painful conditions. Despite this, there has been little in-depth review of the safety of non-aspirin analgesics at OTC doses. This paper reviews the available literature on the gastrointestinal (GI) and hepatic safety of non-aspirin OTC analgesics, including nonsteroidal anti-inflammatory drugs (NSAIDs; ibuprofen, ketoprofen, diclofenac, and naproxen) and acetaminophen; safety in overdose is also reviewed. Each non-aspirin OTC analgesic has a distinct adverse event (AE) profile, with GI AE rates for OTC dosing in one study ranging from 37% for diclofenac to 7.2% for ibuprofen and 7.6% for acetaminophen; GI effects accounted for 75% of total AEs in the study. Across all studies reviewed here, the risk of serious GI toxicity, including upper GI bleeding and peptic ulcers, was low at OTC doses. By contrast, while both NSAIDs and acetaminophen may be associated with hepatotoxicity and acute liver failure (ALF), the risks associated with acetaminophen are somewhat higher and better documented. Reports of NSAID-associated hepatotoxicity rarely make distinctions by dose, making the risk at OTC doses difficult to assess. Liver injury due to acetaminophen, however, can occur at doses < 4000 mg. Case reports of NSAID-associated overdose are rare, while acetaminophen-containing drugs are a leading cause of overdose and are implicated in up to 97% of ALFs leading to transplant involving overdose. OTC analgesics are effective for self-management of pain; however, they are associated with a low but important rate of GI and hepatic events, as well as a risk of intentional and non-intentional overdose. Given the widespread use of this class of drugs, it is important for healthcare professionals to be mindful of their patients' use of OTC analgesics.
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- Analgesic Use and Risk for Acute Coronary Events in Patients With Osteoarthritis: A Population-based, Nested Case-control Study. [Journal Article]
- CTClin Ther 2018; 40(2):270-283
- CONCLUSIONS: In patients with clinically diagnosed OA, the use of nonselective NSAIDs or opioid analgesics is associated with an increased risk for acute coronary events. These risks should be considered when selecting treatments of OA in patients at high cardiovascular risk.