Multimilligram enantioresolution of sulfoxide proton pump inhibitors by liquid chromatography on polysaccharide-based chiral stationary phase

Belaz, K. R. A.; Coimbra, Mariana; Barreiro, Juliana Cristina; Montanari, Carlos Alberto; Cass, Quézia B.

doi:10.1016/j.jpba.2007.12.018

Cited by 24 publications

(11 citation statements)

References 51 publications

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“…[1213] The percentage of methanol between 0 and 10% had strong effect on separation and sharpness of the enantiomeric peaks corresponding to omeprazole. The increase in certain percentage of methanol content in mobile phase drastic increased the resolution, and number of theoretical plates of the two enantiomers, but decreased the resolution with the higher percentage of methanol [Table 1].…”

Section: Resultsmentioning

confidence: 99%

Development and validation of a stability indicating method for the enantioselective estimation of omeprazole enantiomers in the enteric-coated formulations by high-performance liquid chromatography

Vyas¹,

Patel²,

Ladva³

et al. 2011

J Pharm Bioall Sci

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Omeprazole is widely prescribed in the form of enteric-coated formulations, due to the rapid degradation of the drug in the acidic condition of the stomach. In the current article, we are reporting the development and complete validation of a stability indicating chiral high-performance liquid chromatography (HPLC) method for the enantioselective analysis of omeprazole in the enteric-coated formulations. A precise and sensitive enantiomeric separation of omeprazole was obtained on Chiralcel OD-H analytical column (250mm × 4.6 mm, 5μm particle size) using normal phase chromatography. The analysis was performed under UV detection at 301nm wavelength. During method development, the addition of methanol to the mobile phase helped in getting the sharp peaks. The developed method showed linear response over a wide concentration range of 0.39-800μg/ml and the regression coefficients value (r2) was obtained more than 0.999 for (S)- and (R)-omeprazole. The lower limit of detection (LLOD) and lower limit of quantification (LLOQ) for (R)-omeprazole were found to be 0.39 and 0.78 μg/ml, respectively for 5 μl injection volume. The percentage recovery of (R)-omeprazole ranged from 93.5 to 104 in spiked formulation samples and omeprazole sample solution and mobile phase were found to be stable for at least 24 h at room temperature. The proposed method was found to be suitable and accurate for the quantitative determination of undesired enantiomer in the enteric-coated omeprazole formulations.

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Section: Resultsmentioning

confidence: 99%

Development and validation of a stability indicating method for the enantioselective estimation of omeprazole enantiomers in the enteric-coated formulations by high-performance liquid chromatography

Vyas¹,

Patel²,

Ladva³

et al. 2011

J Pharm Bioall Sci

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“…The most frequently used CSPs are polysaccharide-based (amylose and cellulose derivatives). Several research groups contributed to the enantioseparation of PPIs using this type of CSP with remarkable results obtained in developing analytical (Cirilli et al [71][72][73][74][75][76][77]) and bioanalytical (Tanaka et al [48][49][50][51][52], Katsuki et al [54][55][56][57], Cass et al [58][59][60][61][62][63][64][65][66][67][68]) methods and performing pharmacokinetic studies A variety of structurally different cellulose-and amylosederivative CSPs were employed in the analysis of PPIs. Amylose tris(3,5-dimethylphenylcarbamate) was the most frequently used chiral selector, applied in the analysis of all PPIs as well as some of their specific impurities and metabolites, from pharmaceutical, biological and environmental samples.…”

Section: Discussionmentioning

confidence: 99%

Chiral separation in the class of proton pump inhibitors by chromatographic and electromigration techniques: An overview

et al. 2021

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Chiral separation in the class of proton pump inhibitors by chromatographic and electromigration techniques: An overviewProton pump inhibitors (PPIs) are benzimidazole-derivative chiral sulfoxides, frequently used in the treatment of gastric hyperacidity-related disorders. Due to their stereoselective metabolism, the eutomeric forms of PPIs can present a more advantageous pharmacokinetic profile by comparison with the distomers or racemates. Moreover, two representatives of the class are used in therapy both as racemates and as pure enantiomers (esomeprazole, dexlansoprazole). A relatively large number of enantioseparation methods employed for the stereoselective determination of PPIs from pharmaceutical, biological, and environmental matrices were published in the past three decades. The purpose of the current overview is to provide a systematic survey of the available chiral separation methods published since the introduction of PPIs in the therapy up to the present. Analytical and bioanalytical methods using different chromatographic and electromigration techniques reported for the enantioseparation of omeprazole, lansoprazole, pantoprazole, rabeprazole, ilaprazole, and tenatoprazole are included. The analytical conditions of the presented methods are summarized in three comprehensive tables, while a critical discussion of the applied techniques, possible mechanism of enantiorecognition, and future perspectives on the topic are also presented.

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“…Analytical chromatographic separation was carried out using a Daicel (Japan) Chiralpak AD‐H column (250 x 4.6 mm ID, particle size 5 μm). A lab‐made amylose tris(3,5‐dimethylphenylcarbamate) column (200 x 7.0 mm ID, particle size 7 μm), prepared as described elsewhere, was used for semipreparative separation. A solution of racemic LBQ‐118 (60 mg) was prepared in acetonitrile (1 mL), and the supernatant was collected and diluted with acetonitrile (350 μL) before injection.…”

Section: Methodsmentioning

confidence: 99%

Preparative chiral separation and absolute configuration of the synthetic pterocarpanquinone LQB‐118

et al. 2017

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The racemic pterocarpanquinone LQB-118 is active, in mice and hamsters, against tegumentary and visceral leishmaniasis. This compound also presents antiinflammatory and antineoplastic activity in mice. The low level of toxicity observed in these studies makes LQB-118 a promising drug candidate. In order to conduct further biological testing to investigate enantioselectivity in the above-mentioned activities, a multimilligram amount of each enantiomer of LQB-118 was produced. Furthermore, vibrational circular dichroism (VCD) and Density Functional Theory (DFT) calculations were used to determine unambiguously their absolute configurations. The comparison of experimental and calculated VCD data led to the assignment of (-)-LQB-118 as 7aR,12aR and, consequently, (+)-LQB-118 as 7aS12aS.

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Multimilligram enantioresolution of sulfoxide proton pump inhibitors by liquid chromatography on polysaccharide-based chiral stationary phase

Cited by 24 publications

References 51 publications

Development and validation of a stability indicating method for the enantioselective estimation of omeprazole enantiomers in the enteric-coated formulations by high-performance liquid chromatography

Development and validation of a stability indicating method for the enantioselective estimation of omeprazole enantiomers in the enteric-coated formulations by high-performance liquid chromatography

Chiral separation in the class of proton pump inhibitors by chromatographic and electromigration techniques: An overview

Preparative chiral separation and absolute configuration of the synthetic pterocarpanquinone LQB‐118

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