EtOOC -NH N- CH ноос HOOC Enalapril
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? (b) Enalaprilat is a competitive inhibitor of the angiotensin-converting
enzyme (ACE), which cleaves the blood-pressure regulating peptide
angiotensin I. ACE has a KM = 52 μM for angiotensin I, which is present
in plasma at a concentration of 75 μM. When enalaprilat is present
at 2.4 nM, the activity of ACE in plasma is 10% of its uninhibited
activity. What is the value of K1 for enalaprilat?
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