CHEBI:116962 - fosinoprilat

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ChEBI Name fosinoprilat
ChEBI ID CHEBI:116962
Definition A phosphinic acid-containing N-acyl derivative of (4S)-cyclohexyl-L-proline. An inhibitor of angiotensin converting enzyme (ACE), it is used as the phosphinate ester pro-drug fosinopril for treatment of hypertension and chronic heart failure.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C23H34NO5P
Net Charge 0
Average Mass 435.49350
Monoisotopic Mass 435.217
InChI InChI=1S/C23H34NO5P/c25-22(17-30(28,29)14-8-7-11-18-9-3-1-4-10-18)24-16-20(15-21(24)23(26)27)19-12-5-2-6-13-19/h1,3-4,9-10,19-21H,2,5-8,11-17H2,(H,26,27)(H,28,29)/t20-,21+/m1/s1
InChIKey WOIWWYDXDVSWAZ-RTWAWAEBSA-N
SMILES [H][C@]1(C[C@H](N(C1)C(=O)CP(O)(=O)CCCCc1ccccc1)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): 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 fosinoprilat (CHEBI:116962) has role antihypertensive agent (CHEBI:35674)
fosinoprilat (CHEBI:116962) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
fosinoprilat (CHEBI:116962) is a L-proline derivative (CHEBI:84186)
fosinoprilat (CHEBI:116962) is a phosphinic acids (CHEBI:26044)
Incoming fosinopril (CHEBI:5163) has functional parent fosinoprilat (CHEBI:116962)
IUPAC Name
(4S)-4-cyclohexyl-1-{[hydroxy(4-phenylbutyl)phosphoryl]acetyl}-L-proline
INNs Sources
fosinoprilat ChemIDplus
fosinoprilat WHO MedNet
fosinoprilat WHO MedNet
fosinoprilatum ChemIDplus
Synonyms Sources
(2S,4S)-4-cyclohexyl-1-{2-[hydroxy(4-phenylbutyl)phosphoryl]acetyl}pyrrolidine-2-carboxylic acid ChEBI
(2S,4S)-4-cyclohexyl-1-{2-[hydroxy-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid ChEBI
(4S)-4-cyclohexyl-1-((hydroxy(4-phenylbutyl)phosphinyl)acetyl)-L-proline ChemIDplus
4-Cyclohexyl-1-{2-[hydroxy-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid ChEMBL
fosinopril diacid ChemIDplus
fosinoprilic acid ChemIDplus
Database Link Database
D03772 KEGG DRUG
View more database links
Registry Numbers Types Sources
6492772 Beilstein Registry Number Beilstein
6492772 Reaxys Registry Number Reaxys
95399-71-6 CAS Registry Number KEGG DRUG
95399-71-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10606834 PubMed citation Europe PMC
17482898 PubMed citation Europe PMC
7751424 PubMed citation Europe PMC
9549638 PubMed citation Europe PMC
Last Modified
07 January 2015