Enalapril

Enalapril
Clinical data
Trade namesVasotec, Renitec, Enacard, others
AHFS/Drugs.comMonograph
MedlinePlusa686022
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classACE inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability60% (by mouth)
MetabolismLiver (to enalaprilat)
Elimination half-life11 hours (enalaprilat)
ExcretionKidney
Identifiers
IUPAC name
  • (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
  • 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)

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.[4] For heart failure, it is generally used with a diuretic, such as furosemide.[5] It is given by mouth or by injection into a vein.[4] Onset of effects are typically within an hour when taken by mouth and last for up to a day.[4]

Common side effects include headache, tiredness, feeling lightheaded with standing, and cough.[4] Serious side effects include angioedema and low blood pressure.[4] Use during pregnancy is believed to result in harm to the baby.[4] It is in the angiotensin-converting-enzyme (ACE) inhibitor family of medications.[4]

Enalapril was patented in 1978, and came into medical use in 1984.[6] It is on the World Health Organization's List of Essential Medicines.[7] In 2022, it was the 141st most commonly prescribed medication in the United States, with more than 4 million prescriptions.[8][9] It is available as a generic medicine.[10]

  1. ^ a b "Enalapril Use During Pregnancy". Drugs.com. 28 February 2020. Retrieved 13 March 2020.
  2. ^ Cite error: The named reference Vasotec FDA label was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference Aqumeldi EPAR was invoked but never defined (see the help page).
  4. ^ a b c d e f g "Enalaprilat/Enalapril Maleate". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  5. ^ World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 286. hdl:10665/44053. ISBN 9789241547659.
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 467. ISBN 9783527607495. Archived from the original on 20 December 2016.
  7. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  8. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  9. ^ "Enalapril Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  10. ^ "Enalapril maleate: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 24 September 2021.
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