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CHEBI:3011 - benazepril

ChEBI IDCHEBI:3011
ChEBI Namebenazepril
Stars
DefinitionA 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.
Last Modified22 February 2017
DownloadsMolfile
FormulaC24H28N2O5
Net Charge0
Average Mass424.497
Monoisotopic Mass424.19982
SMILES[H][C@]1(N[C@@H](CCc2ccccc2)C(=O)OCC)CCc2ccccc2N(CC(=O)O)C1=O
InChIInChI=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
InChIKeyXPCFTKFZXHTYIP-PMACEKPBSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
bénazéprilWHO MedNet
benazeprilWHO MedNet
benazeprilWHO MedNet
benazeprilumWHO MedNet
Synonyms  Source
BenazeprilKEGG COMPOUND
1H-1-Benzazepine-1-acetic acid, 3-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-2,3,4,5-tetrahydro-2-oxo-, (S-(R*,R*))-ChemIDplus
Manual XrefsDatabases
C06843KEGG COMPOUND
BenazeprilWikipedia
DB00542DrugBank
D07499KEGG DRUG
HMDB0014682HMDB
CPD-15329MetaCyc
EP72352Patent
US4410520Patent
LSM-5609LINCS
299DrugCentral
Registry NumbersSources
Reaxys:4302258Reaxys
CAS:86541-75-5KEGG COMPOUND
CAS:86541-75-5ChemIDplus
Citations