CHEBI:4784 - enalapril

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ChEBI Name enalapril
Definition A dicarboxylic acid monoester that is ethyl 4-phenylbutanoate in which a hydrogen α to the carboxy group is substituted by the amino group of L-alanyl-L-proline (S-configuration).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:116847
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Formula C20H28N2O5
Net Charge 0
Average Mass 376.44670
Monoisotopic Mass 376.19982
InChI InChI=1S/C20H28N2O5/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)/t14-,16-,17-/m0/s1
SMILES CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): EC (peptidyl-dipeptidase A) inhibitor
An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC
Application(s): 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.
EC (peptidyl-dipeptidase A) inhibitor
An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
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ChEBI Ontology
Outgoing enalapril (CHEBI:4784) has functional parent enalaprilat (anhydrous) (CHEBI:4786)
enalapril (CHEBI:4784) has role antihypertensive agent (CHEBI:35674)
enalapril (CHEBI:4784) has role EC (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
enalapril (CHEBI:4784) has role geroprotector (CHEBI:176497)
enalapril (CHEBI:4784) has role prodrug (CHEBI:50266)
enalapril (CHEBI:4784) is a dicarboxylic acid monoester (CHEBI:36244)
enalapril (CHEBI:4784) is a dipeptide (CHEBI:46761)
Incoming enalapril maleate (CHEBI:4785) has part enalapril (CHEBI:4784)
INNs Sources
ánalapril WHO MedNet
enalapril ChemIDplus
enalaprila ChemIDplus
enalaprilum ChemIDplus
Synonyms Sources
(S)-1-(N-(1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-L-proline ChemIDplus
(S)-1-{(S)-2-[1-((S)-Ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylic acid ChEMBL
1-(N-((S)-1-carboxy-3-phenylpropyl)-L-alanyl)-L-proline 1'-ethyl ester ChemIDplus
Manual Xrefs Databases
1005 DrugCentral
4534998 ChemSpider
CPD0-2065 MetaCyc
DB00584 DrugBank
Enalapril Wikipedia
EP12401 Patent
HMDB0014722 HMDB
US4374829 Patent
View more database links
Registry Numbers Types Sources
3657467 Beilstein Registry Number Beilstein
75847-73-3 CAS Registry Number KEGG COMPOUND
75847-73-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10669559 PubMed citation ChEMBL
11523315 PubMed citation Europe PMC
12725609 PubMed citation Europe PMC
19019755 PubMed citation Europe PMC
19549507 PubMed citation Europe PMC
23030053 PubMed citation Europe PMC
23413003 PubMed citation Europe PMC
32835726 PubMed citation Europe PMC
33643971 PubMed citation Europe PMC
33881639 PubMed citation Europe PMC
33963573 PubMed citation Europe PMC
34020248 PubMed citation Europe PMC
34101308 PubMed citation Europe PMC
34412508 PubMed citation Europe PMC
34440064 PubMed citation Europe PMC
34533783 PubMed citation Europe PMC
Last Modified
05 October 2021
General Comment
2011-03-18 Following oral administration, esterases hydrolyse the ethyl ester group 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 is used as the maleate salt 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.