CHEBI:3698 - cilazapril

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ChEBI Name cilazapril
ChEBI ID CHEBI:3698
Definition A pyridazinodiazepine resulting from the formal condensation of the carboxy group of cilazaprilat with ethanol. It is a drug used in the treatment of hypertension and heart failure.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C22H31N3O5
Net Charge 0
Average Mass 417.506
Monoisotopic Mass 417.22637
InChI InChI=1S/C22H31N3O5/c1-2-30-22(29)18(13-12-16-8-4-3-5-9-16)23-17-10-6-14-24-15-7-11-19(21(27)28)25(24)20(17)26/h3-5,8-9,17-19,23H,2,6-7,10-15H2,1H3,(H,27,28)/t17-,18-,19-/m0/s1
InChIKey HHHKFGXWKKUNCY-FHWLQOOXSA-N
SMILES C1CC[C@@H](C(N2N1CCC[C@H]2C(=O)O)=O)N[C@H](C(OCC)=O)CCC3=CC=CC=C3
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): 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.
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).
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ChEBI Ontology
Outgoing cilazapril (CHEBI:3698) has functional parent Cilazaprilat (CHEBI:81005)
cilazapril (CHEBI:3698) has role antihypertensive agent (CHEBI:35674)
cilazapril (CHEBI:3698) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
cilazapril (CHEBI:3698) has role prodrug (CHEBI:50266)
cilazapril (CHEBI:3698) is a dicarboxylic acid monoester (CHEBI:36244)
cilazapril (CHEBI:3698) is a ethyl ester (CHEBI:23990)
cilazapril (CHEBI:3698) is a pyridazinodiazepine (CHEBI:48393)
Incoming cilazapril monohydrate (CHEBI:145568) has part cilazapril (CHEBI:3698)
IUPAC Name
(1S,9S)-9-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-10-oxooctahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
INNs Sources
cilazapril WHO MedNet
cilazapril WHO MedNet
cilazapril WHO MedNet
cilazaprilum WHO MedNet
Synonyms Sources
Cilazapril anhydrous ChemIDplus
Ro 34-2848 ChemIDplus
Brand Names Sources
Dynorm ChEBI
Inhibace KEGG DRUG
Vascace DrugCentral
Vascase ChEBI
Manual Xrefs Databases
641 DrugCentral
Cilazapril Wikipedia
D07699 KEGG DRUG
DB01340 DrugBank
HMDB0015433 HMDB
View more database links
Registry Number Type Source
88768-40-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
18297254 PubMed citation Europe PMC
1836986 PubMed citation Europe PMC
21760854 PubMed citation Europe PMC
24383331 PubMed citation Europe PMC
24754013 PubMed citation Europe PMC
25272892 PubMed citation Europe PMC
28334985 PubMed citation Europe PMC
28445944 PubMed citation Europe PMC
31531043 PubMed citation Europe PMC
Last Modified
28 January 2020