CHEBI:4785 - enalapril maleate

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ChEBI Name enalapril maleate
ChEBI ID CHEBI:4785
Definition The maleic acid salt of enalapril. It contains one molecule of maleic acid for each molecule of enalapril. Following oral administration, the ethyl ester group of enalapril is hydrolysed to afford the corresponding carboxylic acid, enalaprilat, an angiotensin-converting enzyme (ACE) inhibitor. Enalapril is thus a prodrug for enalaprilat (which, unlike enalapril, is not absorbed by mouth), and its maleate is used in the treatment of hypertension and heart failure, for reduction of proteinuria and renal disease in patients with nephropathies, and for the prevention of stroke, myocardial infarction, and cardiac death in high-risk patients.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H32N2O9
Net Charge 0
Average Mass 492.51890
Monoisotopic Mass 492.21078
InChI 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
InChIKey OYFJQPXVCSSHAI-QFPUQLAESA-N
SMILES OC(=O)\C=C/C(O)=O.CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O
Roles Classification
Biological Role(s): EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).
Application(s): EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing enalapril maleate (CHEBI:4785) has part enalapril (CHEBI:4784)
enalapril maleate (CHEBI:4785) has role antihypertensive agent (CHEBI:35674)
enalapril maleate (CHEBI:4785) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
enalapril maleate (CHEBI:4785) has role prodrug (CHEBI:50266)
enalapril maleate (CHEBI:4785) is a maleate salt (CHEBI:50221)
IUPAC Name
N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl-L-proline (2Z)-but-2-enedioate
Synonyms Sources
(S)-1-(N-(1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-L-proline maleate (1:1) ChemIDplus
enalapril hydrogen maleate ChEBI
N-((S)-1-ethoxycarbonyl-3-phenylpropyl)-L-alanyl-L-proline maleate (1:1) ChemIDplus
N-{N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl}-L-proline hydrogen maleate ChEBI
Manual Xrefs Databases
2974 VSDB
D00621 KEGG DRUG
DB00584 DrugBank
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Registry Numbers Types Sources
3645274 Beilstein Registry Number Beilstein
76095-16-4 CAS Registry Number ChemIDplus
76095-16-4 CAS Registry Number KEGG DRUG
Last Modified
27 July 2010