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CHEBI:5163 - fosinopril

ChEBI IDCHEBI:5163
ChEBI Namefosinopril
Stars
DefinitionA 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.
Secondary ChEBI IDsCHEBI:159901, CHEBI:288733
Last Modified22 February 2017
DownloadsMolfile
FormulaC30H46NO7P
Net Charge0
Average Mass563.672
Monoisotopic Mass563.30119
SMILES[H][C@@]1(C2CCCCC2)C[C@@H](C(=O)O)N(C(=O)CP(=O)(CCCCc2ccccc2)OC(OC(=O)CC)C(C)C)C1
InChIInChI=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
InChIKeyBIDNLKIUORFRQP-FKDWWROVSA-N
Roles Classification
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.
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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
fosinoprilChemIDplus
Synonyms  Source
FosinoprilKEGG COMPOUND
(S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acidChEMBL
(2S,4S)-4-cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acidDrugBank
(2S,4S)-4-cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acidChEBI
Manual XrefsDatabases
C07016KEGG COMPOUND
D07992KEGG DRUG
DB00492DrugBank
US4337201Patent
CN101367839Patent
EP2264039Patent
US2010297711Patent
LSM-6485LINCS
Registry NumbersSources
Beilstein:8176492Beilstein
CAS:98048-97-6KEGG COMPOUND
CAS:98048-97-6ChemIDplus
Citations