Figure 22.17 • Metabolism of prilocaine.

_zCH3 O


of action than lidocaine. Prilocaine metabolism has been studied extensively in animal models, less is known about the human metabolites or the human CYP enzymes involved in their formation (Fig. 22.17).88,89 The metabolism of prilo-caine in the liver yields o-toluidine, which is a possible carcinogen. Many aromatic amines, including o-toluidine have been shown to be mutagenic, and metabolites of o-toluidine have been shown to form DNA adducts. Metabolites of o-toluidine are also believed to be responsible for the methemoglobinemia observed with prilocaine use. To decrease the potential for methemoglobinemia, strict adherence to the maximum recommended dose should be followed. Metabolism of prilocaine is extensive with less than 5% of a dose excreted unchanged in the urine.

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