Enalaprilat

Brief Description

Medical use

Enalaprilat is the active metabolite of enalapril. It is the first dicarboxylate-containing ACE inhibitor and was developed partly to overcome these limitations of captopril. The sulfhydryl-moiety was replaced by a carboxylate-moiety, but additional modifications were required in its structure-based design to achieve a potency similar to captopril.

Enalaprilat, however, had a problem of its own. The consequence of the structural modifications was to give it ionisation characteristics that do not allow sufficient GI absorption for oral administration (in tablets). Thus, enalaprilat was only suitable for intravenousadministration. This was overcome by the esterification of enalaprilat with ethanol to produce enalapril.