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: WARNINGRx-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.^[5] For heart failure, it is generally used with a diuretic, such as furosemide.^[6] It is given by mouth or by injection into a vein.^[5] Onset of effects are typically within an hour when taken by mouth and last for up to a day.^[5]

Common side effects include headache, tiredness, feeling lightheaded with standing, and cough.^[5] Serious side effects include angioedema and low blood pressure.^[5] Use during pregnancy is believed to result in harm to the baby.^[5] It is in the angiotensin-converting-enzyme (ACE) inhibitor family of medications.^[5]

Enalapril was patented in 1978, and came into medical use in 1984.^[7] It is on the World Health Organization's List of Essential Medicines.^[8] In 2022, it was the 141st most commonly prescribed medication in the United States, with more than 4 million prescriptions.^[9]^[10] It is available as a generic medicine.^[11]

^ ^a ^b "Enalapril Use During Pregnancy". Drugs.com. 28 February 2020. Retrieved 13 March 2020.
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ Cite error: The named reference Vasotec FDA label was invoked but never defined (see the help page).
^ Cite error: The named reference Aqumeldi EPAR was invoked but never defined (see the help page).
^ ^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.
^ 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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 467. ISBN 9783527607495. Archived from the original on 20 December 2016.
^ 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.
^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
^ "Enalapril Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
^ "Enalapril maleate: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 24 September 2021.

[Drugs.com_pregnancy-1] "Enalapril Use During Pregnancy". Drugs.com. 28 February 2020. Retrieved 13 March 2020.

[FDA-AllBoxedWarnings-2] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[Vasotec_FDA_label-3] Cite error: The named reference Vasotec FDA label was invoked but never defined (see the help page).

[Aqumeldi_EPAR-4] Cite error: The named reference Aqumeldi EPAR was invoked but never defined (see the help page).

[AHFS2016-5] ^ ^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.

[WHO2008-6] 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.

[Fis2006-7] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 467. ISBN 9783527607495. Archived from the original on 20 December 2016.

[WHO23rd-8] 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.

[9] "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.

[10] "Enalapril Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

[11] "Enalapril maleate: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 24 September 2021.

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Enalapril

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