1

Figure 1 Common catalytic groups in hydrolases involved in ester and amide bond hydrolysis: Z+ = electrophilic component polarizing the carbonyl group; Y: = nucleophilic group attacking the carbonyl carbon; H-P = proton donor transforming the -OR' or -NR'R' moiety into a better leaving group. (Reproduced from Testa, B.; Mayer, J. M. Hydrolysis in Drug and Prodrug Metabolism - Chemistry, Biochemistry and Enzymology; Wiley-Verlag Helvetica Chimica Acta: Zurich, Switzerland, 2003, with the kind permission of the copyright owner, Verlag Helvetica Chimica Acta in Zurich.)

Figure 2 The hydrolytic metabolism of cocaine (1) to form benzoylecgonine (2), ecgonine methyl ester (3), and ecgonine (4). In the presence of ethanol, benzoylecgonine ethyl ester (5, cocaethylene) is also formed enzymatically as discussed in the text. (Reproduced from Testa, B.; Mayer, J. M. Hydrolysis in Drug and Prodrug Metabolism - Chemistry, Biochemistry and Enzymology; Wiley-Verlag Helvetica Chimica Acta: Zurich, Switzerland, 2003, with the kind permission of the copyright owner, Verlag Helvetica Chimica Acta in Zurich.)

Figure 2 The hydrolytic metabolism of cocaine (1) to form benzoylecgonine (2), ecgonine methyl ester (3), and ecgonine (4). In the presence of ethanol, benzoylecgonine ethyl ester (5, cocaethylene) is also formed enzymatically as discussed in the text. (Reproduced from Testa, B.; Mayer, J. M. Hydrolysis in Drug and Prodrug Metabolism - Chemistry, Biochemistry and Enzymology; Wiley-Verlag Helvetica Chimica Acta: Zurich, Switzerland, 2003, with the kind permission of the copyright owner, Verlag Helvetica Chimica Acta in Zurich.)

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