Enalapril

Enalapril, sold under the brand name Vasotec among others, is an ACE inhibitor medication used to treat high blood pressure, diabetic kidney disease, and heart failure. For heart failure, it is generally used with a diuretic, such as furosemide. It is given by mouth or by injection into a vein. Onset of effects are typically within an hour when taken by mouth and last for up to a day.

Enalapril
Clinical data
Trade namesVasotec, Renitec, Enacard, others
AHFS/Drugs.comMonograph
MedlinePlusa686022
License data
Pregnancy
category
  • AU: D
  • Contraindicated
Routes of
administration		By mouth
Drug classACE inhibitor
ATC code
Legal status
Legal status
  • US: WARNINGRx-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability60% (by mouth)
MetabolismLiver (to enalaprilat)
Elimination half-life11 hours (enalaprilat)
ExcretionKidney
Identifiers
  • (2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.119.661
Chemical and physical data
FormulaC20H28N2O5
Molar mass376.453 g·mol−1
3D model (JSmol)
Melting point143 to 144.5 °C (289.4 to 292.1 °F)
SMILES
  • O=C(O)[C@H]2N(C(=O)[C@@H](N[C@H](C(=O)OCC)CCc1ccccc1)C)CCC2
  • InChI=1S/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16-,17-/m0/s1 Y
  • Key:GBXSMTUPTTWBMN-XIRDDKMYSA-N Y
  (verify)

Common side effects include headache, tiredness, feeling lightheaded with standing, and cough. Serious side effects include angioedema and low blood pressure. Use during pregnancy is believed to result in harm to the baby. It is in the angiotensin-converting-enzyme (ACE) inhibitor family of medications.

Enalapril was patented in 1978, and came into medical use in 1984. It is on the World Health Organization's List of Essential Medicines. In 2021, it was the 278th most commonly prescribed medication in the United States, with more than 800,000 prescriptions. It is available as a generic medicine.

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