Abstract
Various bispilocarpic acid diesters (double prodrugs of pilocarpine) were synthesized, and theirin vitroesterase catalyzed hydrolysis was evaluated in diluted human plasma, rabbit cornea homogenate, and specific butyrylcholinesterase solution. The structural changes greatly affected the rate of enzymatic hydrolysis of the prodrugs. Bispilocarpic acid with 2 cyclopropane substituents was the most stable derivative, whereas bispilocarpic acid with 2 cyclobutane substituents was the most labile derivative. The charged bispilocarpic acid diester hydrolyzed more slowly than the uncharged form. Comparison of the results obtained from different plasma and cornea homogenate batches is difficult because of the variety of the enzyme systems involved. This variety also makes comparing the results between different laboratories difficult.
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