Structural elucidation of phase I and II metabolites of bupivacaine in horse urine and fungi of the Cunninghamella species using liquid chromatography/multi-stage mass spectrometry

Rapid Communications in Mass Spectrometry : RCM
Axel RydevikMikael Hedeland

Abstract

Bupivacaine is a local anaesthetic prohibited in equine sports. It is highly metabolized in the horse but a thorough description of its metabolite profile is lacking. An administration study should find appropriate analytical targets for doping control. Furthermore, knowledge of an in vitro system for production of metabolites would be beneficial. Marcain® (bupivacaine hydrochloride) was administered subcutaneously to a horse and urine samples were collected. In vitro metabolic systems consisting of the fungi Cunninghamella elegans and Cunninghamella blakesleeana were incubated with bupivacaine and bupivacaine-d(9). Samples were analyzed directly after dilution or cleaned up using liquid-liquid extraction. Separation was achieved with liquid chromatography. Mass spectrometric analysis was performed using positive electrospray ionization with both a tandem quadrupole and an ion trap instrument using MS(n) and hydrogen/deuterium exchange. In horse urine, seven phase I metabolites were found: 3'- and 4'-hydroxybupivacaine, N-desbutylbupivacaine, two aliphatically hydroxylated metabolites, one N-oxide, and dihydroxybupivacaine. Sulfated hydroxybupivacaine and glucuronides of 3'- and 4'-hydroxybupivacaine and of dihydroxybupivacaine...Continue Reading

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Citations

Nov 17, 2012·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·Axel RydevikMikael Hedeland
Jul 23, 2013·Journal of Pharmaceutical and Biomedical Analysis·Axel RydevikMikael Hedeland
Jan 14, 2021·Drug Testing and Analysis·Fernando MoreiraMaria de Lourdes Bastos

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