Enalapril is a prodrug of an ACE inhibitor used to treat hypertension and congestive heart failure.

Brand Names
Epaned, Vaseretic, Vasotec
Generic Name
DrugBank Accession Number

Enalapril is a prodrug belonging to the angiotensin-converting enzyme (ACE) inhibitor drug class that works on the renin-angiotensin-aldosterone system, which is responsible for the regulation of blood pressure and fluid and electrolyte homeostasis. Enalapril is an orally-active and long-acting nonsulphydryl antihypertensive agent that suppresses the renin-angiotensin-aldosterone system to lower blood pressure. It was developed from a targeted research programmed using molecular modelling.2 Being a prodrug, enalapril is rapidly biotransformed into its active metabolite, enalaprilat, which is responsible for the pharmacological actions of enalapril. The active metabolite of enalapril competitively inhibits the ACE to hinder the production of angiotensin II, a key component of the renin-angiotensin-aldosterone system that promotes vasoconstriction and renal reabsorption of sodium ions in the kidneys. Ultimately, enalaprilat works to reduce blood pressure and blood fluid volume.

Commonly marketed under the trade name Vasotec, enalapril was first approved by the FDA in 1985 for the management of hypertension, heart failure, and asymptomatic left ventricular dysfunction. It is also found in a combination product containing hydrochlorothiazide that is used for the management of hypertension. The active metabolite enalaprilat is also available in oral tablets and intravenous formulations for injection.

Small Molecule
Approved, Vet approved
Average: 376.4467
Monoisotopic: 376.199822016
Chemical Formula
  • (S)-1-(N-(1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-L-proline
  • (S)-1-{(S)-2-[1-((S)-Ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylic acid
  • 1-(N-((S)-1-carboxy-3-phenylpropyl)-L-alanyl)-L-proline 1'-ethyl ester
  • ánalapril
  • Enalapril
  • Enalaprila
  • Enalaprilum
External IDs
  • L 154739-01 D
  • MK 421



Indicated for the management of essential or renovascular hypertension 10 as monotherapy or in combination with other antihypertensive agents, such as thiazide diuretics, for an additive effect.Label

Indicated for the treatment of symptomatic congestive heart failure, usually in combination with diuretics and digitalis.Label

Indicated for the management of asymptomatic left ventricular dysfunction in patients with an ejection fraction of ≤ to 35 percent to decrease the rate of development of overt heart failure and the incidence of hospitalization for heart failure.Label

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofDiabetic nephropathy••• •••••
Used in combination to manageHigh blood pressure (hypertension)Combination Product in combination with: Nitrendipine (DB01054)•••••••••••••••••••••• •••••••• •••••••••••• •••••••••• •••• •••••••••••••••••
Used in combination to manageHypertensionCombination Product in combination with: Hydrochlorothiazide (DB00999)••••••••••••
Treatment ofHypertension••• ••••••••••••••
Management ofHypertension••••••••••••
Contraindications & Blackbox Warnings
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Enalapril is an antihypertensive agent that exhibits natriuretic and uricosuric properties. Enalapril lowers blood pressure in all grades of essential and renovascular hypertension, and peripheral vascular resistance without causing an increase in heart rate.6 Individuals with low-renin hypertensive population were still responsive to enalapril.Label The duration of hypertensive effect in the systolic and diastolic blood pressure persists for at least 24 hours following initial administration of a single oral dose, and repeated daily administration of enalapril confers an additional reduction in blood pressure and a steady-state antihypertensive response may take several weeks.7 In patients with severe congestive heart failure and inadequate clinical response to conventional antihypertensive therapies, treatment with enalapril resulted in improvements in cardiac performance as observed by a reduction in both preload and afterload, and improved clinical status long-term.6 Furthermore, enalapril was shown to increase cardiac output and stroke volume while decreasing pulmonary capillary wedge pressure in patients with congestive heart failure refractory to conventional treatment with digitalis and diuretics. In clinical studies, enalapril reduced left ventricular mass, and did not affect cardiac function or myocardial perfusion during exercise.5 Enalapril is not highly associated with the risk of bradycardia unlike most diuretics and beta-blockers 6 and it does not produce rebound hypertension upon discontinuation of therapy.5

Enalapril is not reported to produce hypokalaemia, hyperglycaemia, hyperuricaemia or hypercholesterolaemia. In the kidneys, enalapril was shown to increase renal blood flow and decrease renal vascular resistance. It also augmented the glomerular filtration rate in patients with a glomerular filtration rate less than 80 mL/min.5 When used in combination, enalapril was shown to attenuate the extent of drug-induced hypokalemia caused by hydrochlorothiazide 6 and the antihypertensive effects of both drugs were potentiated.2

Mechanism of action

The renin-angiotensin-aldosterone system (RAAS) is a signaling pathway that works in synergism with the sympathetic system to regulate blood pressure and fluid and electrolyte homeostasis. Activation of this system upon stimulation by different factors, such as low blood pressure and nerve impulses, leads to increased release of norepinephrine (NE) from sympathetic nerve terminals and effects on the vascular growth, vasoconstriction, and salt retention in the kidneys.9 Renin is released from Renin acts on the precursor prottein angiotensinogen, which is a plasma globulin synthesized from the liver, to produce cleaved peptide hormone angiotensin I.9 Angiotensin I then can be further cleaved by ACE to produce angiotensin II, a vasoconstrictive peptide hormone.Label Present in different isoforms, angiotensin converting enzyme (ACE) is peptidyl dipeptidase enzyme expressed in various tissues, including the vascular tissues, such as the heart, brain, and kidneys.9 ACE also plays a role in inactivation of bradykinin, a potent vasodepressor peptide.9,Label Angiotensin II mediates various actions on the body by working on its G-protein coupled receptors, AT1 and AT2.9 It causes direct vasoconstriction of precapillary arterioles and postcapillary venules, inhibits the reuptake of NE thereby increasing available levels, stimulates the release of catecholamines from the adrenal medulla, reduces urinary excretion of sodium ions and water by promoting proximal tubular reabsorption, stimulates synthesis and release of aldosterone from the adrenal cortex, and stimulates hypertrophy of both vascular smooth muscle cells and cardiac myocytes.11

Enalapril is a pharmacologically inactive prodrug that requires hepatic biotransformation to form enalaprilat, its active metabolite that works on the RAAS to inhibit ACE.Label Biotransformation is critial for the therapeutic actions of the drug, as enalapril itself is only a weak inhibitor of ACE.4 ACE inhibition results in reduced production and plasma levels of angiotensin II, increased plasma renin activity due to the loss of feedback inhibition by angiotensin II, and decreased aldosterone secretion.10 However, plasma aldosterone levels usually return to normal during long-term administration of enalapril.7 Decreased levels of angiotensin II subsequently leads to the dilatation of peripheral vessles and reduced vascular resistance which in turn lower blood pressure.7 While inhibition of ACE leading to suppression of RAAS is thought to be the primary mechanism of action of enalapril, the drug was shown to still exert antihypertensive effects on individuals with low-renin hypertension. It is suggested that enalapril may mediate its pharmacological actions via other modes of action that are not fully understood.Label As ACE is structurally similar to kininase I, which is a carboxypeptidase that degrades bradykinin, whether increased levels of bradykinin play a role in the therapeutic effects of enalapril remains to be elucidated.Label

AAngiotensin-converting enzyme

Following oral administration, the peak plasma concentrations (Cmax) of enalapril is achieved within 1 hour post dosing while the Cmax of enalaprilat occurs at three to four hours post dosing.Label The steady-state is achieved by the fourth daily dose and there is no accumulation with repeated dosing.5 However, accumulation of enalaprilat may occur in patients with creatinine clearance less than 30 mL/min.4 Food intake is reported to have a minimal effect on drug absorption.1 Following oral administration, about 60% of enalapril was absorbed.Label Bioavailability of enalapril averaged about 40% when intravenous enalaprilat was used as a reference standard.2

Volume of distribution

The volume of distribution of enalapril has not been established. Enalaprilat is shown to penetrate into most tissuesm, in particular the kidneys and vascular tissuem, although penetration of the blood-brain barrier has not been demonstrated after administration at therapeutic doses.7 In dog studies, enalapril and enalaprilat cross the blood-brain barrier poorly.10 Minimal penetration occurs into breast milk but significant fetal transfer occurs.7 The drug crosses the placental barrier in rats and hamsters.10

Protein binding

It is reported that less than 50% of enalaprilat is bound to human plasma proteins, based on limited data from binding studies of enalaprilat in human plasma both by equilibrium dialysis and by ultrafiltration.2,7


About 60% of the absorbed dose is extensively hydrolyzed to enalaprilat via de-esterification mediated by hepatic esterases.Label In humans, metabolism beyond bioactivation to enalaprilat is not observed.5

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Route of elimination

Enalapril is mainly eliminated through renal excretion, where approximately 94% of the total dose is excreted via urine or feces as either enalaprilat or unchanged parent compound.Label About 61% and 33% of the total dose can be recovered in the urine and feces, respectively.7 In the urine, about 40% of the recovered dose is in the form of enalaprilat.Label


The average terminal half life of enalaprilat is 35-38 hours. The effective half life following multiple doses is 11-14 hours. The prolonged terminal half-life is due to the binding of enalaprilat to ACE.5


Following oral administration in healthy male volunteers, the renal clearance was approximately 158 ± 47 mL/min.8 It is reported that enalapril and enalaprilat are undetectable in the plasma by 4 hours post-dosing.3

Adverse Effects
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LD50 and Overdose

Oral LD50 in rats is 2973 mg/kg.MSDS Lethality was observed with single oral doses of enalapril above 1000 mg/kg in mice and greater than or equal to 1775 mg/kg in rats. Serum enalaprilat levels 100- and 200-fold higher than usually seen after therapeutic doses have been reported after ingestion of 300 mg and 440 mg of enalapril, respectively.10 While there is limited data about enalapril overdose in humans, overdosage may result in marked hypotension and stupor based on the pharmacological properties of the drug. Most common adverse effects of enalapril include cough, hypotension, stupor, headache, dizziness and fatigue. If hypotension is seen, usual treatment of intravenous infusion of normal saline solution is recommended. Enalaprilat may be removed from systemic circulation with the use of hemodialysis. It has been removed from neonatal circulation by peritoneal dialysis.Label

Nonclinical toxicology

Maternal and fetal toxicity occudred in some rabbits treated with enalapril at doses of 1 mg/kg/day or more. There was no fetotoxicity, expressed as a decrease in average fetal weight, or teratogenicity in rats treated with enalapril at doses up to 200 mg/kg/day, which is about 333 times the maximum human dose.10 In mice and rats receiving enalapril at doses ranging from 90 to 180 mg/kg/day, there was no evidence of a tumorigenic effect. Neither enalapril or its active metabolite were shown to be mutagenic or genotoxic in in vitro and in vivo studies. There were no adverse effects on reproductive performance of male and female rats treated with up to 90 mg/kg/day of enalapril. Label

Use in special populations

Caution is warranted in patients who are concurrently using another ACE inhibitors with enalapril, as there have been incidences of agranulocytosis with the use of captopril, which is another ACE inhibitor. This adverse event may be particularly significant in patients with renal impairment or collagen vascular disease.Label As enalapril and enalaprilat were shown to be secreted in human milk in trace amounts, the use of enalaprilat in nursing women is not recommended.10 Significant fetal transfer occurs with enalapril and enalaprilat thus the use of the drug in pregnant women should be strongly avoided. Caution is advised when enalapril is used in patients who are elderly or with renal impairment, as dosage adjustments may be appropriate. The antihypertensive effect of angiotensin converting enzyme inhibitors is generally lower in individuals of African descent, usually a low-renin hypertensive population.Label

Enalapril Metabolism PathwayDrug metabolism
Enalapril Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available


Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
AbaloparatideThe risk or severity of adverse effects can be increased when Enalapril is combined with Abaloparatide.
AcamprosateThe excretion of Acamprosate can be decreased when combined with Enalapril.
AcebutololEnalapril may increase the hypotensive activities of Acebutolol.
AceclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Aceclofenac is combined with Enalapril.
AcemetacinThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Acemetacin is combined with Enalapril.
Food Interactions
  • Avoid hypertensive herbs (e.g. bayberry, blue cohosh, cayenne, ephedra, and licorice). Additive hypertensive effects may occur.
  • Avoid potassium-containing products. Potassium products increase the risk of hyperkalemia.
  • Take with or without food. The absorption is unaffected by food.


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Product Ingredients
IngredientUNIICASInChI Key
Enalapril maleate9O25354EPJ76095-16-4OYFJQPXVCSSHAI-QFPUQLAESA-N
Enalapril sodium94A7UFL2SI149404-21-7FTTHROYWFRGKST-BDURURIASA-M
Active Moieties
Product Images
International/Other Brands
Acetec (Alphapharm) / Acetensil (Grünenthal) / Alapren (Ranbaxy) / Amotac (Mass Pharma) / Amprace (Merck Sharp & Dohme) / Dilvas (Cipla) / Diotensil (Mintlab) / Drepatil (Fada) / Enace (Abbott) / EnaHexal (Sandoz) / Enal (East West) / Enalapoten (Del Bel) / Enpril (Wockhardt) / Feliberal (Silanes) / Gadopril (Gador (Argentina)) / Glioten (Bago) / Kinfil (Nova Argentia (Argentina)) / Vasotec IV (Sandoz (Canada))
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act EnalaprilTablet8 mgOralTEVA Canada Limited2007-10-17Not applicableCanada flag
Act EnalaprilTablet4 mgOralTEVA Canada Limited2007-10-17Not applicableCanada flag
Act EnalaprilTablet16 mgOralTEVA Canada Limited2007-10-17Not applicableCanada flag
Act EnalaprilTablet2 mgOralTEVA Canada Limited2007-10-17Not applicableCanada flag
EnalaprilTablet16 mgOralCobalt LaboratoriesNot applicableNot applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-enalaprilTablet20 mgOralApotex Corporation1993-12-31Not applicableCanada flag
Apo-enalaprilTablet2.5 mgOralApotex Corporation1993-12-31Not applicableCanada flag
Apo-enalaprilTablet10 mgOralApotex Corporation1993-12-31Not applicableCanada flag
Apo-enalaprilTablet5 mgOralApotex Corporation1993-12-31Not applicableCanada flag
Ava-enalaprilTablet20.0 mgOralAvanstra Inc2011-10-112014-08-21Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ACESISTEMEnalapril (20 MG) + Hydrochlorothiazide (12.5 MG)TabletOralAlfasigma s.p.a.2014-07-08Not applicableItaly flag
ACESISTEMEnalapril (20 MG) + Hydrochlorothiazide (12.5 MG)TabletOralAlfasigma s.p.a.2014-07-08Not applicableItaly flag
ACESISTEMEnalapril (20 MG) + Hydrochlorothiazide (12.5 MG)TabletOralAlfasigma s.p.a.2014-07-082022-04-14Italy flag
ATOVEREnalapril maleate (20 MG) + Lercanidipine hydrochloride (20 MG)Tablet, coatedOralRecordati Industria Chimica E Farmaceutica S.P.A.2015-09-22Not applicableItaly flag
ATOVEREnalapril maleate (10 MG) + Lercanidipine hydrochloride (10 MG)Tablet, coatedOralRecordati Industria Chimica E Farmaceutica S.P.A.2014-07-08Not applicableItaly flag


ATC Codes
C09BA02 — Enalapril and diureticsC09BB06 — Enalapril and nitrendipineC09BB02 — Enalapril and lercanidipineC09AA02 — Enalapril
Drug Categories
Chemical TaxonomyProvided by Classyfire
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Organic compounds
Super Class
Organic acids and derivatives
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alternative Parents
Proline and derivatives / Alpha amino acid esters / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Aralkylamines / Fatty acid esters / Benzene and substituted derivatives / Dicarboxylic acids and derivatives
show 10 more
Alpha-amino acid amide / Alpha-amino acid ester / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
dicarboxylic acid monoester, dipeptide (CHEBI:4784)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

CAS number
InChI Key
(2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid


Synthesis Reference

K. S. Keshava Murthy, Andrew Burchat, Gamini Weeratunga, "Sodium enalapril complex and the use thereof to make sodium enalapril." U.S. Patent US5637730, issued February, 1983.

General References
  1. Swanson BN, Vlasses PH, Ferguson RK, Bergquist PA, Till AE, Irvin JD, Harris K: Influence of food on the bioavailability of enalapril. J Pharm Sci. 1984 Nov;73(11):1655-7. [Article]
  2. Davies RO, Gomez HJ, Irvin JD, Walker JF: An overview of the clinical pharmacology of enalapril. Br J Clin Pharmacol. 1984;18 Suppl 2:215S-229S. [Article]
  3. MacFadyen RJ, Meredith PA, Elliott HL: Enalapril clinical pharmacokinetics and pharmacokinetic-pharmacodynamic relationships. An overview. Clin Pharmacokinet. 1993 Oct;25(4):274-82. doi: 10.2165/00003088-199325040-00003. [Article]
  4. Vlasses PH, Larijani GE, Conner DP, Ferguson RK: Enalapril, a nonsulfhydryl angiotensin-converting enzyme inhibitor. Clin Pharm. 1985 Jan-Feb;4(1):27-40. [Article]
  5. Gomez HJ, Cirillo VJ, Irvin JD: Enalapril: a review of human pharmacology. Drugs. 1985;30 Suppl 1:13-24. doi: 10.2165/00003495-198500301-00004. [Article]
  6. Todd PA, Heel RC: Enalapril. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in hypertension and congestive heart failure. Drugs. 1986 Mar;31(3):198-248. doi: 10.2165/00003495-198631030-00002. [Article]
  7. Todd PA, Goa KL: Enalapril. A reappraisal of its pharmacology and therapeutic use in hypertension. Drugs. 1992 Mar;43(3):346-81. doi: 10.2165/00003495-199243030-00005. [Article]
  8. Ulm EH, Hichens M, Gomez HJ, Till AE, Hand E, Vassil TC, Biollaz J, Brunner HR, Schelling JL: Enalapril maleate and a lysine analogue (MK-521): disposition in man. Br J Clin Pharmacol. 1982 Sep;14(3):357-62. doi: 10.1111/j.1365-2125.1982.tb01991.x. [Article]
  9. 22. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 270-271). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
  10. Enalapril Oral Tablets - Product Monograph [Link]
  11. Angiotensin Converting Enzyme Inhibitors (ACEI) - StatPearls [Link]
  12. FDA Approved Drug Products: VASOTEC (enalapril maleate) tablets [Link]
  13. FDA Approved Drug Products: EPANED (enalapril maleate) solution [Link]
  14. FDA Approved Drug Products: LEXXEL (enalapril maleate and felodipine) tablets [Link]
  15. FDA Approved Drug Products: VASERETIC (enalapril maleate and hydrochlorothiazide) tablets [Link]
Human Metabolome Database
KEGG Compound
PubChem Compound
PubChem Substance
Therapeutic Targets Database
RxList Drug Page
Drugs.com Drug Page
PDRhealth Drug Page
FDA label
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Clinical Trials

Clinical Trials
4Active Not RecruitingScreeningHealthy Volunteers (HV)1
4Active Not RecruitingTreatmentChagas Disease / Heart Failure1
4CompletedBasic ScienceCarboxylesterase 1 (CES1) Genotype / CES1 Activity1
4CompletedBasic ScienceCoronavirus Disease 2019 (COVID‑19) / Myocarditis Allergic / Renal Dialysis / Severe Acute Respiratory Syndrome-related Coronavirus / Vaccines / Viral Infections1
4CompletedBasic ScienceHypertension / Syndrome, Metabolic1


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Dosage Forms
TabletOral10.000 mg
TabletOral2.5 mg
TabletOral20.000 mg
Tablet, orally disintegratingOral0.25 mg
TabletOral10.0 mg
TabletOral20.0 mg
TabletOral5.0 mg
Powder, for suspensionOral0.006 g
TabletOral5.254 mg
Capsule, coatedOral
TabletOral30 MG
TabletOral40 MG
TabletOral2 mg / tab
TabletOral2000000 mg
Tablet, film coatedOral5 mg
TabletOral5.1 mg
TabletOral500000 mg
Tablet, coatedOral
TabletOral10 mg/1
TabletOral2.5 mg/1
TabletOral20 mg/1
TabletOral5 mg/1
Tablet, solubleOral10 mg/1
Tablet, solubleOral2.5 mg/1
Tablet, solubleOral20 mg/1
Tablet, solubleOral5 mg/1
TabletOral20.4 mg
Tablet, film coatedOral
TabletOral10 MG
TabletOral5.000 mg
TabletOral10.00 MG
SolutionOral1 mg/1mL
TabletOral5.00 mg
Tablet, extended releaseOral
TabletOral48.31 mg
TabletOral32 mg
TabletOral4.0 mg
TabletOral8.0 mg
TabletOral2 mg
TabletOral16 mg
TabletOral2.0 mg
TabletOral4 mg
TabletOral8 mg
TabletOral20 mg
TabletOral5 mg
Tablet, coatedOral20 mg
Unit descriptionCostUnit
Enalapril maleate powder9.18USD g
Enalaprilat 1.25 mg/ml vial3.6USD ml
Vasotec 20 mg tablet3.36USD tablet
Vaseretic 10-25 mg tablet3.15USD tablet
Vasotec 10 mg tablet2.63USD tablet
Vasotec 5 mg tablet2.08USD tablet
Vasotec 2.5 mg tablet1.65USD tablet
Enalapril maleate 20 mg tablet1.56USD tablet
Vaseretic 5-12.5 mg tablet1.49USD tablet
Vasotec 20 mg Tablet1.34USD tablet
Vasotec 10 mg Tablet1.11USD tablet
Enalapril maleate 10 mg tablet1.09USD tablet
Enalapril maleate 5 mg tablet1.03USD tablet
Vasotec 5 mg Tablet0.92USD tablet
Enalapril maleate 2.5 mg tablet0.82USD tablet
Vasotec 2.5 mg Tablet0.78USD tablet
Apo-Enalapril 20 mg Tablet0.75USD tablet
Co Enalapril 20 mg Tablet0.75USD tablet
Mylan-Enalapril 20 mg Tablet0.75USD tablet
Novo-Enalapril 20 mg Tablet0.75USD tablet
Pms-Enalapril 20 mg Tablet0.75USD tablet
Ratio-Enalapril 20 mg Tablet0.75USD tablet
Sandoz Enalapril 20 mg Tablet0.75USD tablet
Taro-Enalapril 20 mg Tablet0.75USD tablet
Apo-Enalapril 10 mg Tablet0.62USD tablet
Co Enalapril 10 mg Tablet0.62USD tablet
Mylan-Enalapril 10 mg Tablet0.62USD tablet
Novo-Enalapril 10 mg Tablet0.62USD tablet
Pms-Enalapril 10 mg Tablet0.62USD tablet
Ratio-Enalapril 10 mg Tablet0.62USD tablet
Sandoz Enalapril 10 mg Tablet0.62USD tablet
Taro-Enalapril 10 mg Tablet0.62USD tablet
Apo-Enalapril 5 mg Tablet0.52USD tablet
Co Enalapril 5 mg Tablet0.52USD tablet
Mylan-Enalapril 5 mg Tablet0.52USD tablet
Novo-Enalapril 5 mg Tablet0.52USD tablet
Pms-Enalapril 5 mg Tablet0.52USD tablet
Ratio-Enalapril 5 mg Tablet0.52USD tablet
Sandoz Enalapril 5 mg Tablet0.52USD tablet
Taro-Enalapril 5 mg Tablet0.52USD tablet
Apo-Enalapril 2.5 mg Tablet0.44USD tablet
Co Enalapril 2.5 mg Tablet0.44USD tablet
Mylan-Enalapril 2.5 mg Tablet0.44USD tablet
Novo-Enalapril 2.5 mg Tablet0.44USD tablet
Pms-Enalapril 2.5 mg Tablet0.44USD tablet
Ratio-Enalapril 2.5 mg Tablet0.44USD tablet
Sandoz Enalapril 2.5 mg Tablet0.44USD tablet
Taro-Enalapril 2.5 mg Tablet0.44USD tablet
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Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
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US9669008No2017-06-062036-03-25US flag
US9808442No2017-11-072036-03-25US flag
US9855214No2018-01-022032-11-06US flag
US9968553No2018-05-152032-11-06US flag
US10039745No2018-08-072036-03-25US flag
US10154987No2018-12-182036-03-25US flag
US10772868No2020-09-152036-03-25US flag
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Experimental Properties
melting point (°C)143-144.5MSDS
water solubility1.64E+004 mg/LMCFARLAND,JW ET AL. (2001)
logP0.07HANSCH,C ET AL. (1995)
Caco2 permeability-5.64ADME Research, USCD
Predicted Properties
Water Solubility0.213 mg/mLALOGPS
pKa (Strongest Acidic)3.67Chemaxon
pKa (Strongest Basic)5.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area95.94 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity99.57 m3·mol-1Chemaxon
Polarizability40.41 Å3Chemaxon
Number of Rings2Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Human Intestinal Absorption+0.7428
Blood Brain Barrier-0.9659
Caco-2 permeable-0.8956
P-glycoprotein substrateSubstrate0.7691
P-glycoprotein inhibitor INon-inhibitor0.6681
P-glycoprotein inhibitor IINon-inhibitor0.5136
Renal organic cation transporterNon-inhibitor0.8442
CYP450 2C9 substrateNon-substrate0.8632
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5696
CYP450 1A2 substrateNon-inhibitor0.9125
CYP450 2C9 inhibitorNon-inhibitor0.9154
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6825
Ames testNon AMES toxic0.9383
BiodegradationNot ready biodegradable0.8686
Rat acute toxicity1.8269 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9719
hERG inhibition (predictor II)Non-inhibitor0.7456
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)


Mass Spec (NIST)
Not Available
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0udi-4329000000-0ccc991d6f82c8023381
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0809000000-0e192d1573028e60641c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-003r-1859000000-8b202071e8860792a59f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-0329000000-831478ce8de7741826a0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0249000000-1fa4c3835837163595b7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-6923000000-531b7bd3fc250f143a49
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-08i3-2933000000-b16ec6c5a3d022c07ebe
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-2911000000-97697e1a52f2fea8031f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06r6-6911000000-f2027429f1a90f09ec98
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
DarkChem Lite v0.1.0
DarkChem Lite v0.1.0
DeepCCS 1.0 (2019)
DarkChem Lite v0.1.0
DarkChem Lite v0.1.0
DeepCCS 1.0 (2019)
DarkChem Lite v0.1.0
DarkChem Lite v0.1.0
DeepCCS 1.0 (2019)


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Pharmacological action
General Function
Zinc ion binding
Specific Function
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent...
Gene Name
Uniprot ID
Uniprot Name
Angiotensin-converting enzyme
Molecular Weight
149713.675 Da
  1. Andujar-Sanchez M, Jara-Perez V, Camara-Artigas A: Thermodynamic determination of the binding constants of angiotensin-converting enzyme inhibitors by a displacement method. FEBS Lett. 2007 Jul 24;581(18):3449-54. Epub 2007 Jun 27. [Article]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  3. Liu YH, Liu LY, Wu JX, Chen SX, Sun YX: Comparison of captopril and enalapril to study the role of the sulfhydryl-group in improvement of endothelial dysfunction with ACE inhibitors in high dieted methionine mice. J Cardiovasc Pharmacol. 2006 Jan;47(1):82-8. [Article]
  4. Natesh R, Schwager SL, Evans HR, Sturrock ED, Acharya KR: Structural details on the binding of antihypertensive drugs captopril and enalaprilat to human testicular angiotensin I-converting enzyme. Biochemistry. 2004 Jul 13;43(27):8718-24. [Article]


Pharmacological action
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
Uniprot ID
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
  1. Trbojevic-Stankovic J, Aleksic M, Odovic J: Estimation of angiotensin-converting enzyme inhibitors protein binding degree using chromatographic hydrophobicity data. Srp Arh Celok Lek. 2015 Jan-Feb;143(1-2):50-5. [Article]


Pharmacological action
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
Uniprot ID
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
  1. Takara K, Kakumoto M, Tanigawara Y, Funakoshi J, Sakaeda T, Okumura K: Interaction of digoxin with antihypertensive drugs via MDR1. Life Sci. 2002 Feb 15;70(13):1491-500. [Article]
Pharmacological action
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
Uniprot ID
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
  1. Han H, de Vrueh RL, Rhie JK, Covitz KM, Smith PL, Lee CP, Oh DM, Sadee W, Amidon GL: 5'-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter. Pharm Res. 1998 Aug;15(8):1154-9. [Article]
  2. Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. [Article]
  3. Temple CS, Boyd CA: Proton-coupled oligopeptide transport by rat renal cortical brush border membrane vesicles: a functional analysis using ACE inhibitors to determine the isoform of the transporter. Biochim Biophys Acta. 1998 Aug 14;1373(1):277-81. [Article]
  4. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [Article]
Pharmacological action
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
Uniprot ID
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
  1. Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. [Article]
Pharmacological action
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
Uniprot ID
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
  1. Kobayashi Y, Ohshiro N, Tsuchiya A, Kohyama N, Ohbayashi M, Yamamoto T: Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. Drug Metab Dispos. 2004 May;32(5):479-83. [Article]
Pharmacological action
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
Gene Name
Uniprot ID
Uniprot Name
Solute carrier family 22 member 7
Molecular Weight
60025.025 Da
  1. Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. [Article]
  2. Sekine T, Cha SH, Tsuda M, Apiwattanakul N, Nakajima N, Kanai Y, Endou H: Identification of multispecific organic anion transporter 2 expressed predominantly in the liver. FEBS Lett. 1998 Jun 12;429(2):179-82. [Article]
Pharmacological action
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
Uniprot ID
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
  1. Abu-Zahra TN, Wolkoff AW, Kim RB, Pang KS: Uptake of enalapril and expression of organic anion transporting polypeptide 1 in zonal, isolated rat hepatocytes. Drug Metab Dispos. 2000 Jul;28(7):801-6. [Article]
  2. Pang KS, Wang PJ, Chung AY, Wolkoff AW: The modified dipeptide, enalapril, an angiotensin-converting enzyme inhibitor, is transported by the rat liver organic anion transport protein. Hepatology. 1998 Nov;28(5):1341-6. [Article]

Drug created at June 13, 2005 13:24 / Updated at May 27, 2024 21:58