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Enalapril is an anti-hypertension "prodrug" (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? EtOOC -NH CH3 HOOC Enalapril (b) Enalaprilat is a competitive inhibitor of the angiotensin-converting enzyme (ACE), which cleaves the blood-pressure regulating peptide angiotensin. ACE has a KM = 12 µM for angiotensin, 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 uninhib- ited activity. What is the value of K; for enalaprilat?

Enalapril is an anti-hypertension "prodrug" (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? EtOOC -NH CH3 HOOC Enalapril (b) Enalaprilat is a competitive inhibitor of the angiotensin-converting enzyme (ACE), which cleaves the blood-pressure regulating peptide angiotensin. ACE has a KM = 12 µM for angiotensin, 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 uninhib- ited activity. What is the value of K; for enalaprilat?

Biochemistry
Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
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Enalapril is an anti-hypertension "prodrug" (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? EtOOC -NH CH3 HOOC Enalapril (b) Enalaprilat is a competitive inhibitor of the angiotensin-converting enzyme (ACE), which cleaves the blood-pressure regulating peptide angiotensin. ACE has a KM = 12 µM for angiotensin, 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 uninhib- ited activity. What is the value of K; for enalaprilat?
Transcribed Image Text:Enalapril is an anti-hypertension "prodrug" (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? EtOOC -NH CH3 HOOC Enalapril (b) Enalaprilat is a competitive inhibitor of the angiotensin-converting enzyme (ACE), which cleaves the blood-pressure regulating peptide angiotensin. ACE has a KM = 12 µM for angiotensin, 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 uninhib- ited activity. What is the value of K; for enalaprilat?
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