Degradation mechanism for a trace impurity in quinapril drug by tandem mass and precursor ions studies

Shinde, Vikas; Trivedi, Anurag; Upadhayay, Pooja; Gupta, N.L.; Kanase, D. G.; Chikate, Rajeev C.

doi:10.1002/rcm.3167

Cited by 5 publications

(4 citation statements)

References 13 publications

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“…isoquinolinecarboxylic acid hydrochloride [1][2] is a nonpeptide, nonsulfhydryl angiotensin converting enzyme inhibitor (ACEI) belonging to the third class of ACEI [2][3][4]. It is used for the treatment of cardiovascular diseases such as hypertension and congestive heart failure, either alone or in conjunction with other drugs [5][6].…”

Section: Quinapril (3s)-2-[(2s)-2-[[(1s)-1-(ethoxycarbonyl)-3-phenylpmentioning

confidence: 99%

“…Many analytical methods have been reported in the literature for the analysis of quinapril such as gas chromatography with negative-ion chemical ionization mass spectrometry (MS) or electron-capture detection [24], capillary electrophoresis [25], high performance liquid chromatography with fluorescence [24], UV [2] or radiochemical detection [26] as well as electrospray ionization (HPLC/ESI) [2], and MALDI-TOF MS [27]. The considered techniques include also UV spectroscopy [28], square wave voltammetry [29], ultraperformance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) [28], ultra-thin-layer chromatography mass spectrometry and thin-layer chromatography mass spectrometry [30].…”

Section: Quinapril (3s)-2-[(2s)-2-[[(1s)-1-(ethoxycarbonyl)-3-phenylpmentioning

confidence: 99%

“…Indeed, according to the quinapril structure both positive and negative modes could be applied, owing to the carboxylic and amide functional groups of quinapril which could give protons during the ionization process on the one hand, and since both molecules could be protonated on the other hand. In accordance with preliminary investigation as well as with literature data [1][2]31], a positive mode was chosen. Product ion spectra of quinapril and its degradation products were acquired using N 2 as nebulizer and drying gas.…”

Section: Ultra Performance Liquid Chromatography -Tandem Mass Spectromentioning

confidence: 99%

“…Sides [31] and Vikas shinde et al [2]. Indeed, the (+) ESI-MS/MS spectrum of quinapril, with a protonated between the carbon atom of the amide group and the α-carbon, followed by further loss of CH 2 =CH to yield m/z 206 and subsequent elimination of styrene to produce m/z 102.…”

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confidence: 98%

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Forced Degradation Study of Quinapril by UPLC-DAD and UPLC/ MS/MS: Identification of By-products and Development of Degradation Kinetics

Dendeni

Cimetière

Huguet³

et al. 2013

CPA

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Quinapril undergoes a significant degradation in the solid state, especially in the presence of humidity, temperature and pharmaceutical excipients. Since dissolution increases the degradation, hydrolytic reactions are among the most common processes involved in drug degradation. Improving the knowledge regarding drug stability, especially concerning the critical factors that can influence the stability of the active substance in solutions, such as the temperature, the pH and the concentration of catalytic species usually acids or bases is essential for pharmaceutical use; the aim of this study was therefore to develop a new chromatographic method for rapidly and accurately assess the chemical stability of pharmaceutical dosage in acidic, neutral and alkaline media at 80°C according to the ICH guidelines. Ultra High Performance Liquid Chromatography (UPLC) coupled to electrospray ionization tandem mass spectrometry was used for the rapid and simultaneous analysis of quinapril and its by-products. Separation was achieved using a BEH C18 column and a mixture of acetonitrileammonium hydrogencarbonate buffer (pH 8.2; 10 mM) (65:35, v/v) with a flow rate of 0.4 mL/min as a mobile phase. This method allowed the drug by-products profiling, identification, structure elucidation and quantitative determination of by-products under stress conditions. The developed method also provides the determination of the kinetic rate constants for the degradation of quinapril and the formation of its major by-products. Kinetic study and the structure elucidation of by-products allow the development of a complete model including degradation pathway observed under all tested conditions.

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Section: Quinapril (3s)-2-[(2s)-2-[[(1s)-1-(ethoxycarbonyl)-3-phenylpmentioning

confidence: 99%

Section: Quinapril (3s)-2-[(2s)-2-[[(1s)-1-(ethoxycarbonyl)-3-phenylpmentioning

confidence: 99%

Section: Ultra Performance Liquid Chromatography -Tandem Mass Spectromentioning

confidence: 99%

mentioning

confidence: 98%

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Forced Degradation Study of Quinapril by UPLC-DAD and UPLC/ MS/MS: Identification of By-products and Development of Degradation Kinetics

Dendeni

Cimetière

Huguet³

et al. 2013

CPA

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Current literature in mass spectrometry

2007

J. Mass Spectrom.

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In order to keep subscribers up‐to‐date with the latest developments in their field, John Wiley & Sons are providing a current awareness service in each issue of the journal. The bibliography contains newly published material in the field of mass spectrometry. Each bibliography is divided into 11 sections: 1 Reviews; 2 Instrumental Techniques & Methods; 3 Gas Phase Ion Chemistry; 4 Biology/Biochemistry: Amino Acids, Peptides & Proteins; Carbohydrates; Lipids; Nucleic Acids; 5 Pharmacology/Toxicology; 6 Natural Products; 7 Analysis of Organic Compounds; 8 Analysis of Inorganics/Organometallics; 9 Surface Analysis; 10 Environmental Analysis; 11 Elemental Analysis. Within each section, articles are listed in alphabetical order with respect to author (4 Weeks journals ‐ Search completed at 12th. Sept. 2007)

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