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Article

Oxidation and Reduction of Hydrazones—Risk Factors Related to the Manufacture and Stability of the Drugs

by
Anna B. Witkowska
1,2,
Krzysztof Stolarczyk
3,
Massimo Fusaro
3,
Andrzej Leś
3,
Joanna Giebułtowicz
2 and
Elżbieta U. Stolarczyk
1,*
1
Spectrometric Methods Department, National Medicines Institute, Chełmska 30/34, 00-725 Warsaw, Poland
2
Department of Drug Chemistry, Pharmaceutical and Biomedical Analysis, Medical University of Warsaw, 61 Żwirki i Wigury, 02-091 Warsaw, Poland
3
Faculty of Chemistry, University of Warsaw, 1 Pasteura Street, 02-093 Warsaw, Poland
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2025, 26(9), 4295; https://doi.org/10.3390/ijms26094295
Submission received: 30 March 2025 / Revised: 24 April 2025 / Accepted: 28 April 2025 / Published: 1 May 2025
(This article belongs to the Special Issue Novel Strategies in the Development of New Therapies, Drug Substances and Drug Carriers, 3rd Edition)
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Abstract

This study aimed to evaluate the use of electrochemistry to generate the oxidation and reduction products of active pharmaceutical ingredients (APIs) with a hydrazone group, including dantrolene, nitrofurantoin, furazidine, and nitrofural. In the first step, cyclic voltammetry was employed to assess the electroactivity of these compounds. In the second step, the transformation products of selected APIs following electrochemical oxidation and reduction were analyzed using the ROXY EC System equipped with a µ-PrepCell™ 2.0, coupled with a high-resolution Q-TOF mass spectrometer. The identification of transformation products was based on accurate mass, isotopic distribution, and fragmentation pattern. Seventeen API impurities were identified in this study, contributing to insights into drug stability and potential risks associated with their manufacture. Experimental findings were supported by the quantum mechanical DFT calculations of the molecular energies. In addition, using commercially available in silico software, the predicted metabolic products were compared with those obtained by experimental methods. The electrochemical approach proved useful as a test for determining the stability of compounds, the detection of new impurities and structure determination using high-resolution mass spectrometry.
Keywords: oxidation; reduction; stability; electrochemistry; DFT; in silico methods oxidation; reduction; stability; electrochemistry; DFT; in silico methods

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MDPI and ACS Style

Witkowska, A.B.; Stolarczyk, K.; Fusaro, M.; Leś, A.; Giebułtowicz, J.; Stolarczyk, E.U. Oxidation and Reduction of Hydrazones—Risk Factors Related to the Manufacture and Stability of the Drugs. Int. J. Mol. Sci. 2025, 26, 4295. https://doi.org/10.3390/ijms26094295

AMA Style

Witkowska AB, Stolarczyk K, Fusaro M, Leś A, Giebułtowicz J, Stolarczyk EU. Oxidation and Reduction of Hydrazones—Risk Factors Related to the Manufacture and Stability of the Drugs. International Journal of Molecular Sciences. 2025; 26(9):4295. https://doi.org/10.3390/ijms26094295

Chicago/Turabian Style

Witkowska, Anna B., Krzysztof Stolarczyk, Massimo Fusaro, Andrzej Leś, Joanna Giebułtowicz, and Elżbieta U. Stolarczyk. 2025. "Oxidation and Reduction of Hydrazones—Risk Factors Related to the Manufacture and Stability of the Drugs" International Journal of Molecular Sciences 26, no. 9: 4295. https://doi.org/10.3390/ijms26094295

APA Style

Witkowska, A. B., Stolarczyk, K., Fusaro, M., Leś, A., Giebułtowicz, J., & Stolarczyk, E. U. (2025). Oxidation and Reduction of Hydrazones—Risk Factors Related to the Manufacture and Stability of the Drugs. International Journal of Molecular Sciences, 26(9), 4295. https://doi.org/10.3390/ijms26094295

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