Application of high-performance liquid chromatographic chiral stationary phases to pharmaceutical analysis structural and conformational effects in the direct enantiomeric resolution of α-methylarylacetic acid antiinflammatory agents

“…However, a recent study classified naproxen as the least harmful NSAID in cardiovascular terms. 3 Different analytical methods have been proposed for the determination of naproxen in pharmaceutical formulations including spectrophotometry (UV region), 4,5 spectrofluorimetry, [6][7][8] capillary isotachophoresis 9 and high-performance liquid-chromatography (HPLC) coupled with spectrophotometric, 10 amperometric 11 and mass spectrometric detectors. 1 Nevertheless, these analytical methods require expensive equipment and reagents, are time-consuming and often necessitate laborious pre-and post-column derivatization procedures.…”

Section: Introductionmentioning

confidence: 99%

Fast determination of naproxen in pharmaceutical formulations by batch injection analysis with pulsed amperometric detection

Stefano¹,

Lima²,

Montes³

et al. 2012

J. Braz. Chem. Soc.

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Um método eletroanalítico original e rápido para a determinação de naproxeno em formulações farmacêuticas usando análise por injeção em batelada (BIA) com detecção amperométrica pulsada é descrito. Eletrodo de carbono vítreo foi usado como eletrodo de trabalho e solução tampão fosfato 0,05 mol L -1 como eletrólito suporte. O método amperométrico envolveu a aplicação contínua de dois pulsos de potencial ao eletrodo de trabalho com intuito de detectar naproxeno pela sua oxidação eletroquímica (+1,5 V por 200 ms) e de limpar a superfície do eletrodo de produtos de adsorção (+1,0 V por 100 ms), evitando contaminação do eletrodo. O método proposto possui várias vantagens para análises de rotina, incluindo: baixo desvio padrão relativo (3,0%, n = 10), elevada frequência analítica (90 h -1 ), exatidão satisfatória (baseado em determinações comparativas por espectrofluorimetria) e baixo limite de detecção (0,3 µmol L -1 ).A novel and fast electroanalytical method for naproxen determination in pharmaceutical formulations using batch injection analysis (BIA) with pulsed amperometric detection is described. Bare glassy carbon electrode was used as working electrode and 0.05 mol L -1 phosphate buffer solution as supporting electrolyte. The amperometric method involved the continuous application of two sequential potential pulses to the working electrode in order to detect naproxen by its electrochemical oxidation (+1.5 V for 200 ms) and to clean the electrode surface from adsorption products (+1.0 V for 100 ms), avoiding electrode contamination. The proposed method has several advantages for routine analysis, including: a low relative standard deviation between injections (3.0%, n = 10), high analytical frequency (90 h -1 ), satisfactory accuracy (based on comparative determinations by spectrofluorimetry) and low limit of detection (0.3 µmol L -1 ).Keywords: batch injection analysis, multiple-pulse amperometry, non-steroidal antiinflammatory drug IntroductionNaproxen, 2-(6-methoxynaphthalen-2-yl) propanoic acid, is a non-steroidal anti-inflammatory drug (NSAID) derived from propionic acid and has been widely used as an over-the-counter analgesic, anti-inflammatory and antipyretic agent. It is also commonly used for the reduction of stiffness caused by conditions including kidney stones, rheumatoid arthritis and other inflammatory rheumatic diseases. 1,2 NSAIDs have been associated with the increasing number of potentially cardiovascular events. However, a recent study classified naproxen as the least harmful NSAID in cardiovascular terms. 3 Different analytical methods have been proposed for the determination of naproxen in pharmaceutical formulations including spectrophotometry (UV region), 4,5 spectrofluorimetry, 6-8 capillary isotachophoresis 9 and high-performance liquid-chromatography (HPLC) coupled with spectrophotometric, 10 amperometric 11 and mass spectrometric detectors. 1 Nevertheless, these analytical methods require expensive equipment and reagents, are time-consuming and often necessitate laborious pre-and pos...

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“…Moreover, in the D N B type system it is often essential to produce derivatives of the drug before chromatography to incorporate functional groups and to provide necessary interaction sites. In spite of the limitations, DNB stationary phases have been used for the enantiomeric separation of drugs such as ibuprofen and other anti-inflammatory agents (23).…”

Section: H I R a L S T A T I O N A R Y P H A S E S Dinitrobenzoyl Pmentioning

confidence: 99%

Chiral High Performance Liquid Chromatography of Drug Molecules

Mehta¹

1990

J Clin Pharm Ther

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SUMMARYThe individual enantiomers of racemic drugs frequently differ in their biological effects. For pharmacological studies of such drugs there is therefore a need for an effective means of separating and quantifying the enantiomers in biological samples. As their physicochemical properties are similar, the assay of enantiomers is generally regarded as difficult, time-consuming and error-prone. However, recent developments in high performance liquid chromatography (HPLC) chiral stationary phase technology overcome some of these problems and provide a more efficient and reliable way of assaying enantiomeric drugs. I N T R O D U C T I O NMany of the most widely prescribed drugs (warfarin, dysopyramide, ibuprofen, /I-blockers etc.) contain a chiral carbon (also called an asymmetric centre or a chiral centre), i.e. a carbon atom that has four different groups attached. For a drug that possesses a single chiral carbon, a pair of enantiomers (non-superimposable mirror image isomers, also called optical isomers or optical antipodes) exists. However, in most cases such drugs are administered in man as a racemic mixture (or a racemate), i.e. as a mixture of each enantiomer. Individual enantiomers of a racemic drug (also called an enantiomeric drug or a chiral drug) rotate the plane of polarized light in equal but opposite directions and are said to be optically active. A racemic mixture on the other hand is optically inactive because the optical activity of one enantiomer is counteracted by that of the other.Although the majority of the chiral drugs contain one asymmetric carbon, there are some which contain either more than one chiral carbon (e.g. an antifungal drug, griseofulvin, contains two chiral carbons), or contain chiral atoms other than carbon, for example, the anticancer drug cyclophosphamide contains chiral phosphorus in a hetercyclic ring system. Figure 1 shows the structures of some drugs which contain asymmetric atoms.The two enantiomers of a racemic drug frequently differ from one another in pharmacological properties. In most cases one of the enantiomers tends to be much more active than the other. The other enantiomer can be harmful, have totally different 313

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Application of high-performance liquid chromatographic chiral stationary phases to pharmaceutical analysis structural and conformational effects in the direct enantiomeric resolution of α-methylarylacetic acid antiinflammatory agents

Cited by 108 publications

References 5 publications

Enantioselective separation of enantiomeric amides on three amylose-based chiral stationary phases: Effects of backbone and carbamate side chain chiralities

Enantioselective separation of enantiomeric amides on three amylose-based chiral stationary phases: Effects of backbone and carbamate side chain chiralities

Fast determination of naproxen in pharmaceutical formulations by batch injection analysis with pulsed amperometric detection

Chiral High Performance Liquid Chromatography of Drug Molecules

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