UPLC Method for Determination of Eight Flupirtine Impurities in Bulk Substance and Their Characterization by 1H NMR and ESI–MS

Bhosale, Dileep; Nikalje, Anna Pratima

doi:10.1007/s10337-016-3084-2

Chromatographia

2016

DOI: 10.1007/s10337-016-3084-2

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UPLC Method for Determination of Eight Flupirtine Impurities in Bulk Substance and Their Characterization by 1H NMR and ESI–MS

Dileep Bhosale¹,

Anna Pratima Nikalje²

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Cited by 2 publications

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Structure‐Activity Relationships of Flupirtine Analogues for Liver Esterase‐Mediated Cleavage of the 4‐Fluorobenzylamine Moiety and Its Possible Relevance to Liver Toxicity

Beirow

Jedamzik

Schulig³

et al. 2023

ChemMedChem

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Flupirtine and retigabine were essential drugs to combat pain and epilepsy. However, the K v 7 potassium channel openers are fraught with hepatotoxicity and tissue discoloration, respectively, limiting their therapeutic value. Both adverse events are likely due to reactive metabolites arising from oxidative metabolism. Designing safer analogues lacking the structural elements leading to described side effects is an active area of current research. One of the main metabolites of flupirtine is the biologically inactive 4-fluorohippuric acid. Hitherto unexplained, the proposed metabolic pathway leading to the formation of 4-fluorohippuric acid from flupirtine is verified here. Through the use of eighteen flupirtine analogues, mechanistic details of this pathway could be elucidated. A possible connection with the in vitro hepatotoxicity of the flupirtine analogues and the levels of 4-fluorobenzoic acid formed in enzyme incubations was examined by correlation analysis. These findings provide important information for the design of new flupirtine analogues as potential drug candidates.

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Structure‐Activity Relationships of Flupirtine Analogues for Liver Esterase‐Mediated Cleavage of the 4‐Fluorobenzylamine Moiety and Its Possible Relevance to Liver Toxicity

Beirow

Jedamzik

Schulig³

et al. 2023

ChemMedChem

View full text Add to dashboard Cite

show abstract

Development and Validation of Stability-Indicating UPLC Method for 9-Desmethyl-α-dihydrotetrabenazine

et al. 2017

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UPLC Method for Determination of Eight Flupirtine Impurities in Bulk Substance and Their Characterization by 1H NMR and ESI–MS

Cited by 2 publications

References 6 publications

Structure‐Activity Relationships of Flupirtine Analogues for Liver Esterase‐Mediated Cleavage of the 4‐Fluorobenzylamine Moiety and Its Possible Relevance to Liver Toxicity

Structure‐Activity Relationships of Flupirtine Analogues for Liver Esterase‐Mediated Cleavage of the 4‐Fluorobenzylamine Moiety and Its Possible Relevance to Liver Toxicity

Development and Validation of Stability-Indicating UPLC Method for 9-Desmethyl-α-dihydrotetrabenazine

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