Electrochemical oxidation of fesoterodine and identification of its oxidation products using liquid chromatography and mass spectrometry. (20th March 2015)

• Record Type: Journal Article
• Authors: Kučerová, Pavla; Skopalová, Jana; Kučera, Lukáš; Hrbáč, Jan; Lemr, Karel
• Is Part Of: Electrochimica acta. Volume 159(2015)
• Page Start: 131
• Page End: 139
• Publication Date: 2015-03-20
• Subjects: Fesoterodine -- Oxidation -- Hydrolysis -- Voltammetry -- Mass spectrometry; Electrochemistry -- Periodicals; Electrochemistry, Industrial -- Periodicals; 541.37
• DOI: 10.1016/j.electacta.2015.01.190
• Languages: English
• ISSNs: 0013-4686

Abstract

Abstract: The electrochemical behavior of fesoterodine (FES), an antimuscarinic drug used for the treatment of urge incontinence and overactive bladder, was investigated using linear sweep and cyclic voltammetry at a stationary and rotating disc glassy carbon electrodes. A single two-electron anodic signal of FES was observed in neutral buffered aqueous methanolic solutions. Kinetics of alkaline hydrolysis of FES to its active metabolite 5-hydroxymethyl tolterodine was investigated by time dependent linear sweep voltammetry. Controlled potential electrolysis of FES solutions was performed at platinum gauze electrode in aqueous-methanolic media. Electrolyzed solutions were analyzed using ultra performance liquid chromatography with electrospray ionization quadrupole time-of-flight mass spectrometry. Two main products of electrochemical oxidation of fesoterodine were identified as 5-formyl fesoterodine (isobutyric acid 2-(3-diisopropylamino-1-phenyl-propyl)-4-formyl-phenyl ester) and N -desisopropylated fesoterodine (isobutyric acid 4-hydroxymethyl-2-(3-isopropylamino-1-phenyl-propyl)-phenyl ester). The mechanism of the electrochemical oxidation of FES has been proposed and confirmed using on-line electrochemistry/mass spectrometry with porous glassy carbon electrode.