Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H27N2O5.Na |
Molecular Weight | 398.4285 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CCC[C@H]2C([O-])=O
InChI
InChIKey=FTTHROYWFRGKST-BDURURIASA-M
InChI=1S/C20H28N2O5.Na/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);/q;+1/p-1/t14-,16-,17-;/m0./s1
Enalapril (marketed as Vasotec in the US, Enaladex and Renitec in some other countries) is an angiotensin-converting-enzyme (ACE) inhibitor used in the treatment of hypertension, diabetic nephropathy, and some types of chronic heart failure. Enalapril, after hydrolysis to enalaprilat, inhibits angiotensin-converting enzyme (ACE) in human subjects and animals. ACE is a peptidyl dipeptidase that catalyzes the conversion of angiotensin I to the vasoconstrictor substance, angiotensin II. Angiotensin II also stimulates aldosterone secretion by the adrenal cortex. The beneficial effects of enalapril in hypertension and heart failure appear to result primarily from suppression of the renin-angiotensin-aldosterone system. Inhibition of ACE results in decreased plasma angiotensin II, which leads to decreased vasopressor activity and to decrease aldosterone secretion.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1808 |
1.94 nM [IC50] | ||
Target ID: CHEMBL1808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15236580 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | VASOTEC Approved UseHypertension Enalapril maleate is indicated for the treatment of hypertension. Enalapril maleate is effective alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. The blood pressure lowering effects of enalapril maleate and thiazides are approximately additive. Heart Failure Enalapril maleate is indicated for the treatment of symptomatic congestive heart failure, usually in combination with diuretics and digitalis. In these patients enalapril maleate improves symptoms, increases survival, and decreases the frequency of hospitalization (see CLINICAL PHARMACOLOGY, Heart Failure, Mortality Trials for details and limitations of survival trials). Asymptomatic Left Ventricular Dysfunction In clinically stable asymptomatic patients with left ventricular dysfunction (ejection fraction ≤35 percent), enalapril maleate decreases the rate of development of overt heart failure and decreases the incidence of hospitalization for heart failure. (See CLINICAL PHARMACOLOGY, Heart Failure, Mortality Trials for details and limitations of survival trials.) In using enalapril maleate, consideration should be given to the fact that another angiotensin converting enzyme inhibitor, captopril, has caused agranulocytosis, particularly in patients with renal impairment or collagen vascular disease, and that available data are insufficient to show that enalapril maleate does not have a similar risk. (See WARNINGS.) In considering use of enalapril maleate, it should be noted that in controlled clinical trials ACE inhibitors have an effect on blood pressure that is less in black patients than in non-blacks. In addition, it should be noted that black patients receiving ACE inhibitors have been reported to have a higher incidence of angioedema compared to non-blacks. (See WARNINGS, Head and Neck Angioedema.), Hypertension Enalapril maleate is indicated for the treatment of hypertension. Enalapril maleate is effective alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. The blood pressure lowering effects of enalapril maleate and thiazides are approximately additive., Heart Failure Enalapril maleate is indicated for the treatment of symptomatic congestive heart failure, usually in combination with diuretics and digitalis. In these patients enalapril maleate improves symptoms, increases survival, and decreases the frequency of hospitalization (see CLINICAL PHARMACOLOGY, Heart Failure, Mortality Trials for details and limitations of survival trials)., Asymptomatic Left Ventricular Dysfunction In clinically stable asymptomatic patients with left ventricular dysfunction (ejection fraction ≤35 percent), enalapril maleate decreases the rate of development of overt heart failure and decreases the incidence of hospitalization for heart failure. (See CLINICAL PHARMACOLOGY, Heart Failure, Mortality Trials for details and limitations of survival trials.) In using enalapril maleate, consideration should be given to the fact that another angiotensin converting enzyme inhibitor, captopril, has caused agranulocytosis, particularly in patients with renal impairment or collagen vascular disease, and that available data are insufficient to show that enalapril maleate does not have a similar risk. (See WARNINGS.) In considering use of enalapril maleate, it should be noted that in controlled clinical trials ACE inhibitors have an effect on blood pressure that is less in black patients than in non-blacks. In addition, it should be noted that black patients receiving ACE inhibitors have been reported to have a higher incidence of angioedema compared to non-blacks. (See WARNINGS, Head and Neck Angioedema.) Launch Date1985 |
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Palliative | VASOTEC Approved UseHypertension Enalapril maleate is indicated for the treatment of hypertension. Enalapril maleate is effective alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. The blood pressure lowering effects of enalapril maleate and thiazides are approximately additive. Heart Failure Enalapril maleate is indicated for the treatment of symptomatic congestive heart failure, usually in combination with diuretics and digitalis. In these patients enalapril maleate improves symptoms, increases survival, and decreases the frequency of hospitalization (see CLINICAL PHARMACOLOGY, Heart Failure, Mortality Trials for details and limitations of survival trials). Asymptomatic Left Ventricular Dysfunction In clinically stable asymptomatic patients with left ventricular dysfunction (ejection fraction ≤35 percent), enalapril maleate decreases the rate of development of overt heart failure and decreases the incidence of hospitalization for heart failure. (See CLINICAL PHARMACOLOGY, Heart Failure, Mortality Trials for details and limitations of survival trials.) In using enalapril maleate, consideration should be given to the fact that another angiotensin converting enzyme inhibitor, captopril, has caused agranulocytosis, particularly in patients with renal impairment or collagen vascular disease, and that available data are insufficient to show that enalapril maleate does not have a similar risk. (See WARNINGS.) In considering use of enalapril maleate, it should be noted that in controlled clinical trials ACE inhibitors have an effect on blood pressure that is less in black patients than in non-blacks. In addition, it should be noted that black patients receiving ACE inhibitors have been reported to have a higher incidence of angioedema compared to non-blacks. (See WARNINGS, Head and Neck Angioedema.), Hypertension Enalapril maleate is indicated for the treatment of hypertension. Enalapril maleate is effective alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. The blood pressure lowering effects of enalapril maleate and thiazides are approximately additive., Heart Failure Enalapril maleate is indicated for the treatment of symptomatic congestive heart failure, usually in combination with diuretics and digitalis. In these patients enalapril maleate improves symptoms, increases survival, and decreases the frequency of hospitalization (see CLINICAL PHARMACOLOGY, Heart Failure, Mortality Trials for details and limitations of survival trials)., Asymptomatic Left Ventricular Dysfunction In clinically stable asymptomatic patients with left ventricular dysfunction (ejection fraction ≤35 percent), enalapril maleate decreases the rate of development of overt heart failure and decreases the incidence of hospitalization for heart failure. (See CLINICAL PHARMACOLOGY, Heart Failure, Mortality Trials for details and limitations of survival trials.) In using enalapril maleate, consideration should be given to the fact that another angiotensin converting enzyme inhibitor, captopril, has caused agranulocytosis, particularly in patients with renal impairment or collagen vascular disease, and that available data are insufficient to show that enalapril maleate does not have a similar risk. (See WARNINGS.) In considering use of enalapril maleate, it should be noted that in controlled clinical trials ACE inhibitors have an effect on blood pressure that is less in black patients than in non-blacks. In addition, it should be noted that black patients receiving ACE inhibitors have been reported to have a higher incidence of angioedema compared to non-blacks. (See WARNINGS, Head and Neck Angioedema.) Launch Date1985 |
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Palliative | VASOTEC Approved UseHypertension Enalapril maleate is indicated for the treatment of hypertension. Enalapril maleate is effective alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. The blood pressure lowering effects of enalapril maleate and thiazides are approximately additive. Heart Failure Enalapril maleate is indicated for the treatment of symptomatic congestive heart failure, usually in combination with diuretics and digitalis. In these patients enalapril maleate improves symptoms, increases survival, and decreases the frequency of hospitalization (see CLINICAL PHARMACOLOGY, Heart Failure, Mortality Trials for details and limitations of survival trials). Asymptomatic Left Ventricular Dysfunction In clinically stable asymptomatic patients with left ventricular dysfunction (ejection fraction ≤35 percent), enalapril maleate decreases the rate of development of overt heart failure and decreases the incidence of hospitalization for heart failure. (See CLINICAL PHARMACOLOGY, Heart Failure, Mortality Trials for details and limitations of survival trials.) In using enalapril maleate, consideration should be given to the fact that another angiotensin converting enzyme inhibitor, captopril, has caused agranulocytosis, particularly in patients with renal impairment or collagen vascular disease, and that available data are insufficient to show that enalapril maleate does not have a similar risk. (See WARNINGS.) In considering use of enalapril maleate, it should be noted that in controlled clinical trials ACE inhibitors have an effect on blood pressure that is less in black patients than in non-blacks. In addition, it should be noted that black patients receiving ACE inhibitors have been reported to have a higher incidence of angioedema compared to non-blacks. (See WARNINGS, Head and Neck Angioedema.), Hypertension Enalapril maleate is indicated for the treatment of hypertension. Enalapril maleate is effective alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. The blood pressure lowering effects of enalapril maleate and thiazides are approximately additive., Heart Failure Enalapril maleate is indicated for the treatment of symptomatic congestive heart failure, usually in combination with diuretics and digitalis. In these patients enalapril maleate improves symptoms, increases survival, and decreases the frequency of hospitalization (see CLINICAL PHARMACOLOGY, Heart Failure, Mortality Trials for details and limitations of survival trials)., Asymptomatic Left Ventricular Dysfunction In clinically stable asymptomatic patients with left ventricular dysfunction (ejection fraction ≤35 percent), enalapril maleate decreases the rate of development of overt heart failure and decreases the incidence of hospitalization for heart failure. (See CLINICAL PHARMACOLOGY, Heart Failure, Mortality Trials for details and limitations of survival trials.) In using enalapril maleate, consideration should be given to the fact that another angiotensin converting enzyme inhibitor, captopril, has caused agranulocytosis, particularly in patients with renal impairment or collagen vascular disease, and that available data are insufficient to show that enalapril maleate does not have a similar risk. (See WARNINGS.) In considering use of enalapril maleate, it should be noted that in controlled clinical trials ACE inhibitors have an effect on blood pressure that is less in black patients than in non-blacks. In addition, it should be noted that black patients receiving ACE inhibitors have been reported to have a higher incidence of angioedema compared to non-blacks. (See WARNINGS, Head and Neck Angioedema.) Launch Date1985 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
44.27 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29050316 |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENALAPRIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
37.61 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29050316 |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENALAPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
84.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29050316 |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENALAPRIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
372.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29050316 |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENALAPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.75 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29050316 |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENALAPRIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
24.73 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29050316 |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENALAPRILAT plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
22.5 mg 1 times / day multiple, oral (mean) Recommended Dose: 22.5 mg, 1 times / day Route: oral Route: multiple Dose: 22.5 mg, 1 times / day Sources: |
unhealthy, adult n = 276 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: M+F Population Size: 276 Sources: |
Disc. AE: Pruritus, Glossitis... AEs leading to discontinuation/dose reduction: Pruritus (grade 1-3, 0.7%) Sources: Glossitis (grade 1-4, 0.4%) Dry cough (all grades, 1.1%) |
10 mg 1 times / day single, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: single Dose: 10 mg, 1 times / day Sources: Page: nda/2013/204308Orig1s000MedR.pdf - p.40 |
healthy, mean age 32.4 years n = 51 Health Status: healthy Age Group: mean age 32.4 years Sex: M+F Population Size: 51 Sources: Page: nda/2013/204308Orig1s000MedR.pdf - p.40 |
Disc. AE: Dysphagia, Hypotension... AEs leading to discontinuation/dose reduction: Dysphagia (grade 1-2, 2%) Sources: Page: nda/2013/204308Orig1s000MedR.pdf - p.40Hypotension (grade 1-2, 2%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dry cough | all grades, 1.1% Disc. AE |
22.5 mg 1 times / day multiple, oral (mean) Recommended Dose: 22.5 mg, 1 times / day Route: oral Route: multiple Dose: 22.5 mg, 1 times / day Sources: |
unhealthy, adult n = 276 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: M+F Population Size: 276 Sources: |
Pruritus | grade 1-3, 0.7% Disc. AE |
22.5 mg 1 times / day multiple, oral (mean) Recommended Dose: 22.5 mg, 1 times / day Route: oral Route: multiple Dose: 22.5 mg, 1 times / day Sources: |
unhealthy, adult n = 276 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: M+F Population Size: 276 Sources: |
Glossitis | grade 1-4, 0.4% Disc. AE |
22.5 mg 1 times / day multiple, oral (mean) Recommended Dose: 22.5 mg, 1 times / day Route: oral Route: multiple Dose: 22.5 mg, 1 times / day Sources: |
unhealthy, adult n = 276 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: M+F Population Size: 276 Sources: |
Dysphagia | grade 1-2, 2% Disc. AE |
10 mg 1 times / day single, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: single Dose: 10 mg, 1 times / day Sources: Page: nda/2013/204308Orig1s000MedR.pdf - p.40 |
healthy, mean age 32.4 years n = 51 Health Status: healthy Age Group: mean age 32.4 years Sex: M+F Population Size: 51 Sources: Page: nda/2013/204308Orig1s000MedR.pdf - p.40 |
Hypotension | grade 1-2, 2% Disc. AE |
10 mg 1 times / day single, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: single Dose: 10 mg, 1 times / day Sources: Page: nda/2013/204308Orig1s000MedR.pdf - p.40 |
healthy, mean age 32.4 years n = 51 Health Status: healthy Age Group: mean age 32.4 years Sex: M+F Population Size: 51 Sources: Page: nda/2013/204308Orig1s000MedR.pdf - p.40 |
PubMed
Title | Date | PubMed |
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Severe childhood pemphigus vulgaris aggravated by enalapril. | 2001 |
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Barnidipine. | 2001 |
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Modulation of the renin-angiotensin system may alter the adrenocortical regeneration. | 2001 |
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Aspirin and ACE-inhibitors: for wedding or funeral? | 2001 Apr |
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Involvement of angiotensin II in progression of renal injury in rats with genetic non-insulin-dependent diabetes mellitus (Wistar fatty rats). | 2001 Apr |
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Angiotensin converting enzyme inhibitor suppresses glomerular transforming growth factor beta receptor expression in experimental diabetes in rats. | 2001 Apr |
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Comparison of a vasopeptidase inhibitor with neutral endopeptidase and angiotensin-converting enzyme inhibitors on bradykinin metabolism in the rat coronary bed. | 2001 Apr |
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Different potentiating effects of imidapril and enalapril on kaolin-induced writhing reaction in mice. | 2001 Apr 13 |
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Determination of the antihypertensive drug cilazapril and its active metabolite cilazaprilat in pharmaceuticals and urine by solid-phase extraction and high-performance liquid chromatography with photometric detection. | 2001 Apr 15 |
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Comparison of candesartan versus enalapril in essential hypertension. Italian Candesartan Study Group. | 2001 Feb |
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Effects of the replacement of the angiotensin converting enzyme inhibitor enalapril by the angiotensin II receptor blocker telmisartan in patients with congestive heart failure. The replacement of angiotensin converting enzyme inhibition (REPLACE) investigators. | 2001 Feb |
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Angiotensin converting enzyme inhibitor induced hyperkalaemic paralysis. | 2001 Feb |
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Treatment of congestive heart failure: guidelines for the primary care physician and the heart failure specialist. | 2001 Feb 12 |
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Volume-weighted mean nuclear volume and numerical nuclear density in the cardiomyocyte following enalapril and verapamil treatment. | 2001 Jan |
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Losartan, an angiotensin type I receptor antagonist, improves conduit vessel endothelial function in Type II diabetes. | 2001 Jan |
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Protective role of enalapril for chronic tubulointerstitial lesions of hyperoxaluria. | 2001 Jul |
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Remission achieved in chronic nephropathy by a multidrug approach targeted at urinary protein excretion. | 2001 Jul |
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Effect of the drug-matrix on the stability of enalapril maleate in tablet formulations. | 2001 Jul |
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Effects of the vasopeptidase inhibitor omapatrilat on cardiac endogenous kinins in rats with acute myocardial infarction. | 2001 Jun |
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Comparison of effects of losartan versus enalapril on fibrinolysis and coagulation in patients with acute myocardial infarction. | 2001 Jun 15 |
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A retrospective analysis comparing the costs and cost effectiveness of amlodipine and enalapril in the treatment of hypertension. | 2001 Mar |
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Beneficial effects of nicorandil versus enalapril in chronic rheumatic severe mitral regurgitation: six months follow up echocardiographic study. | 2001 Mar |
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Angiotensin-converting enzyme inhibitor dosages in elderly patients with heart failure. | 2001 Mar |
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Does enalapril prevent peritoneal fibrosis induced by hypertonic (3.86%) peritoneal dialysis solution? | 2001 Mar-Apr |
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A randomized and double-blind comparison of isradipine and spirapril as monotherapy and in combination on the decline in renal function in patients with chronic renal failure and hypertension. | 2001 May |
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Angiotensin type 1 receptor antagonism and ACE inhibition produce similar renoprotection in N(omega)-nitro-L>-arginine methyl ester/spontaneously hypertensive rats. | 2001 May |
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Bradykinin stimulates the release of tissue plasminogen activator in human coronary circulation: effects of angiotensin-converting enzyme inhibitors. | 2001 May |
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Reversible renal impairment induced by treatment with the angiotensin II receptor antagonist candesartan in a patient with bilateral renal artery stenosis. | 2001 May 17 |
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Lesser response to angiotensin-converting-enzyme inhibitor therapy in black as compared with white patients with left ventricular dysfunction. | 2001 May 3 |
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Effect of column temperature on the behaviour of some angiotensin converting enzyme inhibitors during high-performance liquid chromatographic analysis. | 2001 May 5 |
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The effect of enalapril on advanced diabetic nephropathy in African-American females. | 2001 Spring-Summer |
Patents
Sample Use Guides
Hypertension: The recommended initial dose in patients not on diuretics is 5 mg once a day.
Dosage Adjustment in Hypertensive Patients with Renal Impairment: The usual dose of enalapril is recommended for patients with a creatinine clearance >30 mL/min (serum
creatinine of up to approximately 3 mg/dL). For patients with creatinine clearance ≤30 mL/min (serum creatinine ≥3 mg/dL), the first dose is 2.5 mg once daily. The dosage may be titrated upward until blood pressure is controlled or to a maximum of 40 mg daily.
Heart Failure: The recommended initial dose is 2.5 mg. The recommended dosing range is 2.5 to 20 mg given twice a day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11124597
Primary cultures of human proximal tubular cells (PTC) and renal cortical fibroblasts (CF) were exposed for 24 h to CyA in the presence or absence of enalaprilat (enalapril is a prodrug that is rapidly metabolized by liver esterases to enalaprilat). Enalaprilat completely reversed the stimulatory effects of CyA on CF collagen synthesis (CyA + enalaprilat 6.40 +/- 0.50% vs. CyA alone 8.33 +/- 0.56% vs. control 6.57 +/- 0.62% vs. enalaprilat alone 5.55 +/- 0.93%, p < 0.05) and PTC secretion of TGFbeta1 (0.71 +/- 0.11, 1.13 +/- 0.09, 0.89 +/- 0.07, and 0.67 +/- 0.09 ng/mg protein/day, respectively, p < 0.05).
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SUBSTANCE RECORD