Optical resolution of imidapril hydrochloride by highperformance liquid chromatography and application to the optical purity testing of drugs

Nishi, Hiroyuki; Yamasaki, Kazuya; Kokusenya, Yoshio; Satô, Tadashi

doi:10.1016/0021-9673(94)80600-4

Cited by 14 publications

(5 citation statements)

References 7 publications

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“…Upon stress testing of IMD with alkali, the drug underwent degradation giving a diacid derivative of IMD through hydrolysis of ester linkage on the basis of the studies of Nishi et al [2] . Degradation of IMD was also examined upon stress testing using peroxide.…”

Section: Resultsmentioning

confidence: 99%

“…IMD, with an ethyl ester structure, is converted into a dicarboxy-type compound (imidaprilat) in the body. Imidaprilat shows about a 500 times higher activity than the ester form, IMD [2] . From the literature survey on the subject, many methods have already been tested including HPLC and GC methods with the use of MS detector [3] , [4] , [5] , [6] , [7] , chiral LC method [2] , other HPLC methods [8] , [9] , densitometry [1] and spectrophotometric determinations [8] , [10] .…”

Section: Introductionmentioning

confidence: 92%

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Determination of a novel ACE inhibitor in the presence of alkaline and oxidative degradation products using smart spectrophotometric and chemometric methods

Hegazy

Eissa

El-Sattar

et al. 2014

Journal of Pharmaceutical Analysis

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Simple, accurate, sensitive and validated UV spectrophotometric and chemometric methods were developed for the determination of imidapril hydrochloride (IMD) in the presence of both its alkaline (AKN) and oxidative (OXI) degradation products and in its pharmaceutical formulation. Method A is the fourth derivative spectra (D4) which allows the determination of IMD in the presence of both AKN and OXD, in pure form and in tablets by measuring the peak amplitude at 243.0 nm. Methods B, C and D, manipulating ratio spectra, were also developed. Method B is the double divisor–ratio difference spectrophotometric one (DD–RD) by computing the difference between the amplitudes of IMD ratio spectra at 232 and 256.3 nm. Method C is the double divisor-first derivative of ratio spectra method (DD–DR1) at 243.2 nm, while method D is the mean centering of ratio spectra (MCR) at 288.0 nm. Methods A, B, C and D could successfully determine IMD in a concentration range of 4.0–32.0 µg/mL. Methods E and F are principal component regression (PCR) and partial least-squares (PLS), respectively, for the simultaneous determination of IMD in the presence of both AKN and OXI, in pure form and in its tablets. The developed methods have the advantage of simultaneous determination of the cited components without any pre-treatment. The accuracy, precision and linearity ranges of the developed methods were determined. The results obtained were statistically compared with those of a reported HPLC method, and there was no significant difference between the proposed methods and the reported method regarding both accuracy and precision.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 92%

Determination of a novel ACE inhibitor in the presence of alkaline and oxidative degradation products using smart spectrophotometric and chemometric methods

Hegazy

Eissa

El-Sattar

et al. 2014

Journal of Pharmaceutical Analysis

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“…Among various chiral amino compounds, a chiral amine L-alanine--naphtylamide hydrobromide (L-Ala--NA, see Fig. 2) was successfully applied for the enantiomer separation of naproxen (NX, Naixan ® , a nonsteroidal anti-inflammatory drug) [8], imidapril hydrochloride (TAL, Tanatril ® , an ACE-I inhibitor) [9], a drug candidate, acetyl-L-carnitine (L-AC) [10]. Derivatization of NX was performed in chloroform and N,N'-dicyclohexylcarboimide (DCC), and derivatives were separated by a Zorbax Sil column (4.6 mm ID x 15 cm, 40 o C, flow rate 1.0 mL/min, 254 nm) with the mobile phase CHCl 3 /CH 3 OH = 500/3 within 10 min (Rs 6.6, R-form > S-form (NX)).…”

Section: Enantiomer Separation Of Pharmaceuticals By Hplc and Its Appmentioning

confidence: 99%

“…Further the separation of enantiomers of 8-chloroderivative of HER (clentiazem) was successful by the OVM column [13]. Other than protein immobilized CSPs, enantiomers of TAL were separated by a ligand-exchange type CSP, a CHIRALPAK WH column [9], enantiomers of L-AC were separated by a SUMICHILAL OA-6100 column (4.6 mm ID x 15 cm, 40 o C, flow rate 1.0 mL/min, 254 nm), employing a bulky acid (0.5 mol/L NaClO 4 ) and 2 mmoL/L Cu 2+ as the mobile phase [15] (see, Fig. 3B).…”

Section: Enantiomer Separation Of Pharmaceuticals By Hplc and Its Appmentioning

confidence: 99%

Development of Fast and Selective Analytical Methods of Pharmaceuticals and Herbal Medicines by High-Performance Liquid Chromatography and Capillary Electrophoresis

Nishi

2021

Chromatography

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Pharmaceuticals are essential for the medical treatment of various diseases. From the herbal medicines (crude drugs), synthetic medicines to biopharmaceuticals, to assure its efficacy and safety, the production procedures and the quality control methods of pharmaceuticals are important. These are strictly regulated by Good Manufacturing Practice (GMP) and various guidelines. The key is to develop the "Specifications and testing methods" of the pharmaceutical scientifically and rationally according to the production process. There are many testing items such as identity tests, purity tests, assay, etc. in "Specifications and testing methods". Among them, assay and purity test are core testing items. Optical purity evaluation is required for the single enantiomer pharmaceutical. Chromatographic methods and its detection methods are useful for the purpose. High-performance liquid chromatography (HPLC), thin layer chromatography (TLC) and gas chromatography (GC) are commonly used because the target analyses are almost a mixture. In this review, results of the development of the quality evaluation methods of relatively low molecular pharmaceuticals and herbal medicines by HPLC and capillary electrophoresis (CE) we have been investigated are summarized.

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“…In 1994, direct separation of the enantiomers of imidapril hydrochloride, which previously required chiral derivatization, was achieved by using the CSP Chiralpak WH, a ligand-exchange type column where Cu 2C is used as a mobile phase additive. 88 With this method, good linearity between the peak area and the amount of sample used, combined with a signalto-noise ratio of 3, gave a detection limit of about 0.2% for the antipode. In our laboratory approximately 70% of chiral separations of drugs have been achieved by using CSPs.…”

Section: Chiral Stationary Phasesmentioning

confidence: 99%

Chiral Purity in Drug Analysis

Machida¹,

Nishi²

2000

Encyclopedia of Analytical Chemistry

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The preparation and evaluation of optically active compounds have become very important for the development of new drugs. The determination of chiral purity of drugs is essential in order to guarantee safety and effectiveness. Isomeric impurities may have unwanted toxicological, pharmacological, or other side‐effects. Therefore we decided to prepare an article entitled “Chiral purity in drug analysis”. This article is divided into five sections (introduction, production, regulation, evaluation methods and conclusion). In the introduction, the importance of assessing the isomeric impurities in drug analysis will be discussed. In the second section, production methods for optically active compounds, except the stereoselective synthesis method, will be summarized briefly. In particular, new trends in the production of chiral drugs, such as the simulated moving beds (SMB) method, will be described. In the third section, regulatory perspectives in the USA (Food and Drug Administration (FDA)), EC, and Japan will be described and some regulatory guidelines and guidances by, for example, the FDA, the Committee for Veterinary Medicinal Products (CVMP), and the International Conference on Harmonization (ICH) will be mentioned. In the fourth section, methods for the determination of stereoisomeric drugs will be summarized. Methods such as gas chromatography (GC), high‐performance liquid chromatography (HPLC), and capillary electrophoresis (CE) have been summarized. The focus will be on direct evaluation methods, i.e. those using chiral stationary phases (CSPs). Practical details for testing a drug's optical purity are also given.

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Optical resolution of imidapril hydrochloride by highperformance liquid chromatography and application to the optical purity testing of drugs

Cited by 14 publications

References 7 publications

Determination of a novel ACE inhibitor in the presence of alkaline and oxidative degradation products using smart spectrophotometric and chemometric methods

Determination of a novel ACE inhibitor in the presence of alkaline and oxidative degradation products using smart spectrophotometric and chemometric methods

Development of Fast and Selective Analytical Methods of Pharmaceuticals and Herbal Medicines by High-Performance Liquid Chromatography and Capillary Electrophoresis

Chiral Purity in Drug Analysis

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