CHEBI:3011 - benazepril

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ChEBI Name benazepril
ChEBI ID CHEBI:3011
Definition A benzazepine that is benazeprilat in which the carboxy group of the 2-amino-4-phenylbutanoic acid moiety has been converted to the corresponding ethyl ester. It is used (generally as its hydrochloride salt) as a prodrug for the angiotensin-converting enzyme inhibitor benazeprilat in the treatment of hypertension and heart failure.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H28N2O5
Net Charge 0
Average Mass 424.48950
Monoisotopic Mass 424.200
InChI InChI=1S/C24H28N2O5/c1-2-31-24(30)20(14-12-17-8-4-3-5-9-17)25-19-15-13-18-10-6-7-11-21(18)26(23(19)29)16-22(27)28/h3-11,19-20,25H,2,12-16H2,1H3,(H,27,28)/t19-,20-/m0/s1
InChIKey XPCFTKFZXHTYIP-PMACEKPBSA-N
SMILES CCOC(=O)[C@H](CCc1ccccc1)N[C@H]1CCc2ccccc2N(CC(O)=O)C1=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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).
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 benazepril (CHEBI:3011) has functional parent benazeprilat (CHEBI:88200)
benazepril (CHEBI:3011) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
benazepril (CHEBI:3011) has role prodrug (CHEBI:50266)
benazepril (CHEBI:3011) is a benzazepine (CHEBI:35676)
benazepril (CHEBI:3011) is a dicarboxylic acid monoester (CHEBI:36244)
benazepril (CHEBI:3011) is a ethyl ester (CHEBI:23990)
benazepril (CHEBI:3011) is a lactam (CHEBI:24995)
benazepril (CHEBI:3011) is conjugate base of benazepril(1+) (CHEBI:88201)
Incoming benazepril(1+) (CHEBI:88201) is conjugate acid of benazepril (CHEBI:3011)
IUPAC Name
[(3S)-3-{[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino}-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl]acetic acid
INNs Sources
bénazépril WHO MedNet
benazepril WHO MedNet
benazepril WHO MedNet
benazeprilum WHO MedNet
Synonyms Sources
1H-1-Benzazepine-1-acetic acid, 3-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-2,3,4,5-tetrahydro-2-oxo-, (S-(R*,R*))- ChemIDplus
Benazepril KEGG COMPOUND
Manual Xrefs Databases
299 DrugCentral
Benazepril Wikipedia
C06843 KEGG COMPOUND
CPD-15329 MetaCyc
D07499 KEGG DRUG
DB00542 DrugBank
EP72352 Patent
HMDB0014682 HMDB
LSM-5609 LINCS
US4410520 Patent
View more database links
Registry Numbers Types Sources
4302258 Reaxys Registry Number Reaxys
86541-75-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
25224804 PubMed citation Europe PMC
25738503 PubMed citation Europe PMC
25784709 PubMed citation Europe PMC
25912588 PubMed citation Europe PMC
Last Modified
22 February 2017