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CHEBI:5163 - fosinopril

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ChEBI Name fosinopril
ChEBI ID CHEBI:5163
Definition A phosphinate ester-containing N-acyl derivative of (4S)-cyclohexyl-L-proline. It is used for the treatment of hypertension and heart failure. A pro-drug, it is hydrolysed in vivo to the corresponding phosphininc acid, fosinoprilat, which is the active metabolite.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:288733, CHEBI:159901
Supplier Information
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Formula C30H46NO7P
Net Charge 0
Average Mass 563.66250
Monoisotopic Mass 563.301
InChI InChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)/t25-,26+,30?,39?/m1/s1
InChIKey BIDNLKIUORFRQP-FKDWWROVSA-N
SMILES [H][C@]1(C[C@H](N(C1)C(=O)CP(=O)(CCCCc1ccccc1)OC(OC(=O)CC)C(C)C)C(O)=O)C1CCCCC1
Roles Classification
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.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing fosinopril (CHEBI:5163) has functional parent fosinoprilat (CHEBI:116962)
fosinopril (CHEBI:5163) has role antihypertensive agent (CHEBI:35674)
fosinopril (CHEBI:5163) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
fosinopril (CHEBI:5163) has role prodrug (CHEBI:50266)
fosinopril (CHEBI:5163) is a L-proline derivative (CHEBI:84186)
fosinopril (CHEBI:5163) is a phosphinic ester (CHEBI:26043)
fosinopril (CHEBI:5163) is conjugate acid of fosinopril(1−) (CHEBI:59125)
Incoming fosinopril(1−) (CHEBI:59125) is conjugate base of fosinopril (CHEBI:5163)
IUPAC Name
(4S)-4-cyclohexyl-1-({[2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl}acetyl)-L-proline
INN Source
fosinopril ChemIDplus
Synonyms Sources
(2S,4S)-4-cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid DrugBank
(2S,4S)-4-cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid ChEBI
(S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid ChEMBL
Fosinopril KEGG COMPOUND
Database Links Databases
C07016 KEGG COMPOUND
CN101367839 Patent
D07992 KEGG DRUG
DB00492 DrugBank
EP2264039 Patent
LSM-6485 LINCS
US2010297711 Patent
US4337201 Patent
View more database links
Registry Numbers Types Sources
8176492 Beilstein Registry Number Beilstein
98048-97-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11937741 PubMed citation Europe PMC
18209565 PubMed citation Europe PMC
22729889 PubMed citation Europe PMC
8285178 PubMed citation Europe PMC
9195116 PubMed citation Europe PMC
Last Modified
25 February 2016