Enalapril

Enalapril
Clinical data
Trade names	Vasotec, Renitec, Enacard, others
AHFS/Drugs.com	Monograph
MedlinePlus	a686022
License data	US DailyMed: Enalapril;
Pregnancy; category	AU: D; Contraindicated;
Routes of; administration	By mouth
Drug class	ACE inhibitor
ATC code	C09AA02 (WHO) ;
Legal status
Legal status	US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	60% (by mouth)
Metabolism	Liver (to enalaprilat)
Elimination 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 ;
PubChem CID	5388962;
IUPHAR/BPS	6322;
DrugBank	DB00584 ;
ChemSpider	4534998 ;
UNII	69PN84IO1A;
KEGG	D07892 ;
ChEBI	CHEBI:4784 ;
ChEMBL	ChEMBL578 ;
CompTox Dashboard (EPA)	DTXSID5022982 ;
ECHA InfoCard	100.119.661
Chemical and physical data
Formula	C20H28N2O5
Molar mass	376.453 g·mol−1
3D model (JSmol)	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 ; Key:GBXSMTUPTTWBMN-XIRDDKMYSA-N ;
	(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. 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.

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 2022, it was the 141st most commonly prescribed medication in the United States, with more than 4 million prescriptions. It is available as a generic medicine.