Enalapril is an anti-hypertension "pro-drug" (i.e., a drug precursor) that is inactive until the ethyl ester (arrow in figure)

Question

Enalapril is an anti-hypertension "pro-drug" (i.e., a drug precursor) that is inactive until the ethyl ester (arrow in figure) is hydrolyzed by esterases present in blood plasma. The active drug is the dicarboxylic acid ("enalaprilat") that results from this hydrolysis reaction. 
a. Enalapril is administered in pill form, but enalaprilat must be administered intravenously. Why do you suppose enalapril works as a pill but enalaprilat does not?

Kunduz · Accepted Answer

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