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In vitro hydrolysis of steroid acid ester derivatives of prednisolone in plasma of different species.

The in vitro hydrolysis of two new classes of steroid acid esters synthesized from prednisolone as local anti-inflammatory steroids was investigated in rat, rabbit, and human plasma. One class was synthesized by incorporating methoxycarbonyl groups at the 16 position of prednisolone to produce 16 alpha-methoxycarbonyl prednisolone (P16CM) and its 17-deoxy analogue (DP16CM). The other class was synthesized by modifying the ketol side chain of prednisolone to produce methyl 20 alpha- and methyl beta-dihydroprednisolonate (P4 alpha and P4 beta). The P16CM and P4 beta were rapidly and completely hydrolyzed within 1 h of incubation in rat and rabbit plasma and within 4 h in human plasma. There was a marked species difference in the hydrolysis of DP16CM which occurred in the following order: rat greater than human greater than rabbit. The in vitro hydrolysis of P4 alpha was much slower than that of P4 beta; the process continued over 24 h in rat plasma. As expected, no change in the initial concentration of prednisolone was found over 120 h of incubation in rat plasma. This marked species difference in the hydrolysis of these steroid acid esters is probably related to the differences in the amounts, types, and activities of the hydrolyzing enzymes (e.g., esterases) in the plasma of the three species. From this study it can be concluded that the existence of an hydroxyl group at C-17 and the orientation of hydroxyl groups at C-20 play an important role in the systemic hydrolysis rate of the carboxy ester group on the steroid nucleus.