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CHEBI:4785 - enalapril maleate

ChEBI IDCHEBI:4785
ChEBI Nameenalapril maleate
Stars
DefinitionThe 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.
Last Modified27 July 2010
DownloadsMolfile
FormulaC20H28N2O5.C4H4O4
Net Charge0
Average Mass492.525
Monoisotopic Mass492.21078
SMILESCCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)O.O=C(O)/C=C\C(=O)O
InChIInChI=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
InChIKeyOYFJQPXVCSSHAI-QFPUQLAESA-N
Roles Classification
Biological Role:
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).
Applications:
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).
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.
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
ChEBI Ontology
Outgoing Relation(s)
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  Source
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 maleateChEBI
(S)-1-(N-(1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-L-proline maleate (1:1)ChemIDplus
enalapril hydrogen maleateChEBI
Manual XrefsDatabases
D00621KEGG DRUG
DB00584DrugBank
2974VSDB
Registry NumbersSources
Beilstein:3645274Beilstein
CAS:76095-16-4KEGG DRUG
CAS:76095-16-4ChemIDplus