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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H28N2O5.C4H4O4
Molecular Weight 492.5189
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ENALAPRIL MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CCC[C@H]2C(O)=O

InChI

InChIKey=OYFJQPXVCSSHAI-QFPUQLAESA-N
InChI=1S/C20H28N2O5.C4H4O4/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;5-3(6)1-2-4(7)8/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25);1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,16-,17-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C20H28N2O5
Molecular Weight 376.4467
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

PubMed

PubMed

TitleDatePubMed
Severe childhood pemphigus vulgaris aggravated by enalapril.
2001
Barnidipine.
2001
Perindopril: an updated review of its use in hypertension.
2001
The role of angiotensin II receptor antagonists in the management of diabetes.
2001
The effect duration of candesartan cilexetil once daily, in comparison with enalapril once daily, in patients with mild to moderate hypertension.
2001
The effect of enalapril and verapamil on the left ventricular hypertrophy and the left ventricular cardiomyocyte numerical density in rats submitted to nitric oxide inhibition.
2001 Apr
Aspirin and ACE-inhibitors: for wedding or funeral?
2001 Apr
Involvement of angiotensin II in progression of renal injury in rats with genetic non-insulin-dependent diabetes mellitus (Wistar fatty rats).
2001 Apr
Angiotensin-converting enzyme inhibitors and AT1-receptor antagonist restore nitric oxide synthase (NOS) activity and neuronal NOS expression in the adrenal glands of spontaneously hypertensive rats.
2001 Apr
Angiotensin converting enzyme inhibitor suppresses glomerular transforming growth factor beta receptor expression in experimental diabetes in rats.
2001 Apr
The effects of allicin and enalapril in fructose-induced hyperinsulinemic hyperlipidemic hypertensive rats.
2001 Apr
Different potentiating effects of imidapril and enalapril on kaolin-induced writhing reaction in mice.
2001 Apr 13
Cyclosporine induces myocardial connective tissue growth factor in spontaneously hypertensive rats on high-sodium diet.
2001 Apr 15
Abnormality of the myocardial sympathetic nervous system in a patient with Becker muscular dystrophy detected with iodine-123 metaiodobenzylguanidine scintigraphy.
2001 Aug
Low-dose ACE with alpha- or beta-adrenergic receptor inhibitors have beneficial SHR cardiovascular effects.
2001 Jan
Angiotensin-converting enzyme inhibition with enalapril slows progressive intima-media thickening of the common carotid artery in patients with non-insulin-dependent diabetes mellitus.
2001 Jul
Protective role of enalapril for chronic tubulointerstitial lesions of hyperoxaluria.
2001 Jul
IgA nephropathy and inhibitors of the renin angiotensin system: is reduction in proteinuria adequate proof of efficacy?
2001 Jul
Coadministration of losartan and enalapril exerts additive antiproteinuric effect in IgA nephropathy.
2001 Jul
Remission achieved in chronic nephropathy by a multidrug approach targeted at urinary protein excretion.
2001 Jul
Effect of the drug-matrix on the stability of enalapril maleate in tablet formulations.
2001 Jul
The quantitative determination of several inhibitors of the angiotensin-converting enzyme by CE.
2001 Jul
Weight reduction and pharmacologic treatment in obese hypertensives.
2001 Jun
Effects of various antihypertensive drugs on the function of osteoblast.
2001 Jun
Effects of the vasopeptidase inhibitor omapatrilat on cardiac endogenous kinins in rats with acute myocardial infarction.
2001 Jun
Dyslipidemia and hypertension: twin killers in renal vascular disease.
2001 Jun
The effects of enalapril-digoxin-diuretic combination therapy on nutritional and anthropometric indices in chronic congestive heart failure: preliminary findings in cardiac cachexia.
2001 Jun
Comparison of effects of losartan versus enalapril on fibrinolysis and coagulation in patients with acute myocardial infarction.
2001 Jun 15
Differential effects of nifedipine and co-amilozide on the progression of early carotid wall changes.
2001 Jun 19
The influence of chronic antihypertensive treatment on the central pressor response in SHR.
2001 Mar
Heart biometry and allometry in rats submitted to nitric oxide synthesis blockade and treatment with antihypertensive drugs.
2001 Mar
Does enalapril prevent peritoneal fibrosis induced by hypertonic (3.86%) peritoneal dialysis solution?
2001 Mar-Apr
Comparison of the angiotensin II type 1-receptor antagonist YM358 and the angiotensin-converting enzyme inhibitor enalapril in rats with cardiac volume overload.
2001 May
Influence of ACE-inhibition on salt-mediated worsening of pulmonary gas exchange in heart failure.
2001 May
Low birth weight-associated adult hypertension in the rat.
2001 May
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
Effect of antihypertensive therapy using enalapril or losartan on haemostatic markers in essential hypertension: a pilot prospective randomised double-blind parallel group trial.
2001 May
Angiotensin type 1 receptor antagonism and ACE inhibition produce similar renoprotection in N(omega)-nitro-L>-arginine methyl ester/spontaneously hypertensive rats.
2001 May
Bradykinin stimulates the release of tissue plasminogen activator in human coronary circulation: effects of angiotensin-converting enzyme inhibitors.
2001 May
The bladder angiotensin system in female rats: response to infusions of angiotensin I and the angiotensin converting enzyme inhibitor enalaprilat.
2001 May
Suppression of experimental abdominal aortic aneurysms in the rat by treatment with angiotensin-converting enzyme inhibitors.
2001 May
Hypertensive rebound after angiotensin converting enzyme inhibitor withdrawal in diabetic patients with chronic renal failure.
2001 May
The effect of ACE inhibitor and angiotensin II receptor antagonist therapy on serum uric acid levels and potassium homeostasis in hypertensive renal transplant recipients treated with CsA.
2001 May
Resetting baroreceptors to a lower arterial pressure level by enalapril avoids baroreflex mediated activation of sympathetic nervous system by nifedipine.
2001 May 11
Improved survival with simendan after experimental myocardial infarction in rats.
2001 May 11
Reversible renal impairment induced by treatment with the angiotensin II receptor antagonist candesartan in a patient with bilateral renal artery stenosis.
2001 May 17
Racial differences in the response to drugs--pointers to genetic differences.
2001 May 3
Lesser response to angiotensin-converting-enzyme inhibitor therapy in black as compared with white patients with left ventricular dysfunction.
2001 May 3
Effect of column temperature on the behaviour of some angiotensin converting enzyme inhibitors during high-performance liquid chromatographic analysis.
2001 May 5
The effect of enalapril on advanced diabetic nephropathy in African-American females.
2001 Spring-Summer
Patents

Sample Use Guides

In Vivo Use Guide
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
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).
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:26:59 UTC 2019
Edited
by admin
on Tue Oct 22 00:26:59 UTC 2019
Record UNII
9O25354EPJ
Record Status Validated (UNII)
Record Version
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Name Type Language
ENALAPRIL MALEATE
EP   GREEN BOOK   HSDB   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
VASERETIC COMPONENT ENALAPRIL MALEATE
Common Name English
MK-421
Code English
ENACARD
Brand Name English
ENALAPRIL MALEATE [JAN]
Common Name English
ENALAPRIL MALEATE COMPONENT OF VASERETIC
Common Name English
ENALAPRIL MALEATE [USP-RS]
Common Name English
1-(N-((S)-1-CARBOXY-3-PHENYLPROPYL)-L-ALANYL)-L-PROLINE 1'-ETHYL ESTER, MALEATE
Common Name English
L-PROLINE, 1-(N-(1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)-L-ALANYL)-,(S)-,(Z)-2 BUTENEDIOATE (1:1)
Common Name English
RENITEN
Brand Name English
EPANED
Brand Name English
ENALAPRIL MALEATE [USP]
Common Name English
CARDIOVET
Brand Name English
ENALAPRIL MALEATE [GREEN BOOK]
Common Name English
ENALAPRIL MALEATE COMPONENT OF TECZEM
Common Name English
INNOVACE
Brand Name English
ENALAPRIL MALEATE [WHO-DD]
Common Name English
ENALAPRIL MALEATE COMPONENT OF LEXXEL
Common Name English
HIPOARTEL
Brand Name English
LEXXEL COMPONENT ENALAPRIL MALEATE
Common Name English
RENITEC
Brand Name English
ENALAPRIL MALEATE [VANDF]
Common Name English
AMPRACE
Brand Name English
GLIOTEN
Brand Name English
NAPRILENE
Brand Name English
ENALAPRIL MALEATE [HSDB]
Common Name English
XANEF
Brand Name English
RENIVACE
Brand Name English
TECZEM COMPONENT ENALAPRIL MALEATE
Common Name English
ENALAPRIL MALEATE [MART.]
Common Name English
ENAPREN
Brand Name English
ENALAPRIL MALEATE [MI]
Common Name English
ENALAPRIL MALEATE [USAN]
Common Name English
VASOTEC
Brand Name English
ENALAPRIL MALEATE [ORANGE BOOK]
Common Name English
ENALAPRIL MALEATE [EP]
Common Name English
PRES
Brand Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 376712
Created by admin on Tue Oct 22 00:26:59 UTC 2019 , Edited by admin on Tue Oct 22 00:26:59 UTC 2019
NCI_THESAURUS C247
Created by admin on Tue Oct 22 00:26:59 UTC 2019 , Edited by admin on Tue Oct 22 00:26:59 UTC 2019
Code System Code Type Description
HSDB
76095-16-4
Created by admin on Tue Oct 22 00:26:59 UTC 2019 , Edited by admin on Tue Oct 22 00:26:59 UTC 2019
PRIMARY
ECHA (EC/EINECS)
278-375-7
Created by admin on Tue Oct 22 00:26:59 UTC 2019 , Edited by admin on Tue Oct 22 00:26:59 UTC 2019
PRIMARY
PUBCHEM
5388961
Created by admin on Tue Oct 22 00:26:59 UTC 2019 , Edited by admin on Tue Oct 22 00:26:59 UTC 2019
PRIMARY
CAS
76095-16-4
Created by admin on Tue Oct 22 00:26:59 UTC 2019 , Edited by admin on Tue Oct 22 00:26:59 UTC 2019
PRIMARY
MERCK INDEX
M4893
Created by admin on Tue Oct 22 00:26:59 UTC 2019 , Edited by admin on Tue Oct 22 00:26:59 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C468
Created by admin on Tue Oct 22 00:26:59 UTC 2019 , Edited by admin on Tue Oct 22 00:26:59 UTC 2019
PRIMARY
EVMPD
SUB01884MIG
Created by admin on Tue Oct 22 00:26:59 UTC 2019 , Edited by admin on Tue Oct 22 00:26:59 UTC 2019
PRIMARY
RXCUI
203123
Created by admin on Tue Oct 22 00:26:59 UTC 2019 , Edited by admin on Tue Oct 22 00:26:59 UTC 2019
PRIMARY RxNorm
ChEMBL
CHEMBL578
Created by admin on Tue Oct 22 00:26:59 UTC 2019 , Edited by admin on Tue Oct 22 00:26:59 UTC 2019
PRIMARY
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