Enalapril

Enalapril

Clinical data
Trade names	Vasotec, Renitec, Enacard, others
AHFS/Drugs.com	Monograph
MedlinePlus	a686022
Pregnancy category	D
Routes of administration	by mouth
ATC code	C09AA02 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	60% (by mouth)
Metabolism	liver (to enalaprilat)
Biological half-life	11 hours (enalaprilat)
Excretion	kidney
Identifiers
IUPAC name (2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid
CAS Number	75847-73-3 Y
PubChem CID	5388962
IUPHAR/BPS	6322
DrugBank	DB00584 Y
ChemSpider	4534998 Y
UNII	69PN84IO1A
KEGG	D07892 Y
ChEBI	CHEBI:4784 Y
ChEMBL	CHEMBL578 Y
ECHA InfoCard	100.119.661
Chemical and physical data
Formula	C20H28N2O5
Molar mass	376.447 g/mol
3D model (Jmol)	Interactive image
Melting point	143 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

Enalapril, sold under the brand name Vasotec among others, is a 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 injection into a vein. Onset of effects are typically within an hour when taken by mouth and last for up to day.

Common side effects include headache, tiredness, lightheadedness 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. Enalapril is in the angiotensin-converting-enzyme inhibitor (ACEi) 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, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 0.08 to 0.80 USD per month. In the United States it costs about 25 to 50 USD per month.

Enalapril is used to treat hypertension, symptomatic heart failure, and asymptomatic left ventricular dysfunction. It has been proven to protect the function of the kidneys in hypertension, heart failure, and diabetes, and may be used in the absence of hypertension for its kidney protective effects. It is widely used in chronic kidney failure. Furthermore, enalapril is an emerging treatment for psychogenic polydipsia. A double-blind, placebo-controlled trial showed that when used for this purpose, enalapril lead to decreased water consumption (determined by urine output and osmality) in 60% of patients.