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Enalapril, sold under the brand name Vasotec among others, is a medication used to treat high blood pressure, diabetic kidney disease, and heart failure.
Common side effects include headache, tiredness, lightheadedness with standing, and cough.
Enalapril was patented in 1978 and came into medical use in 1984.
1 Medical uses
1.1 Pregnancy and breastfeeding
2 Side effects
3 Mechanism of action
7 External links
Enalapril three-dimensional structure
Enalapril is used to treat hypertension, symptomatic heart failure, and asymptomatic left ventricular dysfunction.
Pregnancy and breastfeeding
Enalapril is pregnancy category D. Some evidence suggests it will cause injury and death to a developing fetus. Patients are advised not to become pregnant while taking enalapril and to notify their doctors immediately if they become pregnant. In pregnancy, enalapril may result in damage to the fetus’s kidneys and resulting oligohydramnios (not enough amniotic fluid). Enalapril is secreted in breast milk and is not recommended for use while breastfeeding.
The most common side effects of enalapril include increased serum creatinine (20%), dizziness (2–8%), low blood pressure (1–7%), syncope (2%), and dry cough (1–2%). The most serious common adverse event is angioedema (swelling) (0.68%) which often affects the face and lips, endangering the patient’s airway. Angioedema can occur at any point during treatment with enalapril, but is most common after the first few doses.
Mechanism of action
See also: Renin–angiotensin system
Normally, angiotensin I is converted to angiotensin II by an angiotensin-converting enzyme (ACE). Angiotensin II constricts blood vessels, increasing blood pressure. Enalaprilat, the active metabolite of enalapril, inhibits ACE. Inhibition of ACE decreases levels of angiotensin II, leading to less vasoconstriction and decreased blood pressure.
Pharmacokinetic data of enalapril:
Onset of action: about 1 hour
Peak effect: 4–6 hours
Duration: 12–24 hours
Metabolism: prodrug, undergoes biotransformation to enalaprilat
Squibb developed the first ACE inhibitor, captopril, but it had adverse effects such as a metallic taste (which, as it turned out, was due to the sulfhydryl group). Merck & Co. developed enalapril as a competing prodrug. : 12–13
Enalaprilat 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 in that it had poor oral availability. This was overcome by the researchers at Merck by the esterification of enalaprilat with ethanol to produce enalapril. : 13
Merck introduced enalapril to market in 1981; it became Merck’s first billion dollar-selling drug in 1988.
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