Page last updated: 2024-12-06

libenzapril

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

Lisinopril is an angiotensin-converting enzyme (ACE) inhibitor, a type of medication primarily used to treat hypertension and heart failure. It is a prodrug, meaning that it is inactive when administered but is converted to its active form in the body. Lisinopril's mechanism of action involves inhibiting the enzyme ACE, which is responsible for converting angiotensin I to angiotensin II. Angiotensin II is a potent vasoconstrictor, meaning it narrows blood vessels, leading to increased blood pressure. By blocking the conversion of angiotensin I to angiotensin II, lisinopril reduces vasoconstriction, thereby lowering blood pressure. Lisinopril is also studied for its potential role in preventing heart attacks and strokes. It is widely used and is generally well-tolerated, although side effects can occur. The drug is available as a generic medication and is considered a cornerstone treatment for hypertension.'

libenzapril: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID71320
CHEMBL ID430554
CHEBI ID177593
SCHEMBL ID295229
MeSH IDM0148105

Synonyms (27)

Synonym
CHEBI:177593
(2s)-6-amino-2-[[(3s)-1-(carboxymethyl)-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]amino]hexanoic acid
109214-55-3
D03758
libenzapril (usan/inn)
libenzapril [usan:inn]
libenzapril
1h-1-benzazepine-1-acetic acid, 3-((5-amino-1-carboxypentyl)amino)-2,3,4,5-tetrahydro-2-oxo-, (s-(r*,r*))
n-((3s)-1-(carboxymethyl)-2,3,4,5-tetrahydro-2-oxo-1h-1-benzazepin-3-yl)-l-lysine
cgs 16617
cgs-16617
CHEMBL430554 ,
abutapril
6-amino-2-(1-carboxymethyl-2-oxo-2,3,4,5-tetrahydro-1h-benzo[b]azepin-3-ylamino)-hexanoic acid
bdbm50021142
qd8496wwyk ,
unii-qd8496wwyk
1h-1-benzazepine-1-aceticacid, 3-[[(1s)-5-amino-1-carboxypentyl]amino]-2,3,4,5-tetrahydro-2-oxo-, (3s)-
libenzapril [inn]
libenzapril [mart.]
libenzapril [who-dd]
1h-1-benzazepine-1-acetic acid, 3-(((1s)-5-amino-1-carboxypentyl)amino)-2,3,4,5-tetrahydro-2-oxo-, (3s)-
libenzapril [usan]
SCHEMBL295229
1h-1-benzazepine-1acetic acid,3-[[(1s)-5-amino-1-carboxypentyl]amino]-2,3,4,5-tetrahydro-2-oxo-,(3s)-
Q27287204
AKOS040748746

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"Libenzapril, an angiotensin converting enzyme inhibitor, was administered to healthy male volunteers in a randomized, two-phase pharmacokinetic study."( Pharmacodynamic dependent disposition of the angiotensin converting enzyme inhibitor, libenzapril.
Choi, RL; deSilva, JK; Kochak, GM; Reydel-Bax, P, 1990
)
1.95

Bioavailability

ExcerptReferenceRelevance
" The absolute bioavailability was estimated at less than 10% and the renal clearance following oral administration exhibited additional route dependency."( Pharmacodynamic dependent disposition of the angiotensin converting enzyme inhibitor, libenzapril.
Choi, RL; deSilva, JK; Kochak, GM; Reydel-Bax, P, 1990
)
0.5
"The intrasubject and intersubject variabilities for CGS 16617, an angiotensin converting enzyme inhibitor, were evaluated in an open-label, repeat single-dose bioavailability trial."( Intra- and intersubject variability: mixed-effects statistical analysis of repeated doses of an angiotensin converting enzyme inhibitor, CGS 16617.
Choi, RL; deSilva, JK; Honc, F; John, V; Kochak, GM; Smith, RA; Tipnis, V; Weidler, DJ, 1989
)
0.28

Dosage Studied

ExcerptRelevanceReference
" The dose-response curves of contractions obtained with ANG I or ANG II as well as the dose-dependent inhibition of ANG I-induced responses in the presence of CGS 16617 were similar for carotids taken from both WKY and SHR."( Rapid reversal of angiotensin I-induced contractions in rat carotid arteries after acute and chronic treatment with the angiotensin-converting enzyme inhibitor, 3-[(5-amino-1-carboxy-1S-pentyl)amino]2,3,4,5-tetrahydro-2-oxo- 3S-1H-1-benzazepena-1-acetic a
Levens, NR; Sturm, B; Weiss, GB, 1993
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
dipeptideAny molecule that contains two amino-acid residues connected by peptide linkages.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Angiotensin-converting enzyme Homo sapiens (human)IC50 (µMol)0.00700.00010.533610.0000AID38860
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (56)

Processvia Protein(s)Taxonomy
response to hypoxiaAngiotensin-converting enzyme Homo sapiens (human)
kidney developmentAngiotensin-converting enzyme Homo sapiens (human)
blood vessel remodelingAngiotensin-converting enzyme Homo sapiens (human)
angiotensin maturationAngiotensin-converting enzyme Homo sapiens (human)
regulation of renal output by angiotensinAngiotensin-converting enzyme Homo sapiens (human)
neutrophil mediated immunityAngiotensin-converting enzyme Homo sapiens (human)
antigen processing and presentation of peptide antigen via MHC class IAngiotensin-converting enzyme Homo sapiens (human)
regulation of systemic arterial blood pressure by renin-angiotensinAngiotensin-converting enzyme Homo sapiens (human)
proteolysisAngiotensin-converting enzyme Homo sapiens (human)
spermatogenesisAngiotensin-converting enzyme Homo sapiens (human)
female pregnancyAngiotensin-converting enzyme Homo sapiens (human)
regulation of blood pressureAngiotensin-converting enzyme Homo sapiens (human)
male gonad developmentAngiotensin-converting enzyme Homo sapiens (human)
response to xenobiotic stimulusAngiotensin-converting enzyme Homo sapiens (human)
embryo development ending in birth or egg hatchingAngiotensin-converting enzyme Homo sapiens (human)
post-transcriptional regulation of gene expressionAngiotensin-converting enzyme Homo sapiens (human)
negative regulation of gene expressionAngiotensin-converting enzyme Homo sapiens (human)
substance P catabolic processAngiotensin-converting enzyme Homo sapiens (human)
bradykinin catabolic processAngiotensin-converting enzyme Homo sapiens (human)
regulation of smooth muscle cell migrationAngiotensin-converting enzyme Homo sapiens (human)
regulation of vasoconstrictionAngiotensin-converting enzyme Homo sapiens (human)
animal organ regenerationAngiotensin-converting enzyme Homo sapiens (human)
response to nutrient levelsAngiotensin-converting enzyme Homo sapiens (human)
response to lipopolysaccharideAngiotensin-converting enzyme Homo sapiens (human)
mononuclear cell proliferationAngiotensin-converting enzyme Homo sapiens (human)
response to laminar fluid shear stressAngiotensin-converting enzyme Homo sapiens (human)
angiotensin-activated signaling pathwayAngiotensin-converting enzyme Homo sapiens (human)
vasoconstrictionAngiotensin-converting enzyme Homo sapiens (human)
hormone metabolic processAngiotensin-converting enzyme Homo sapiens (human)
hormone catabolic processAngiotensin-converting enzyme Homo sapiens (human)
eating behaviorAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of apoptotic processAngiotensin-converting enzyme Homo sapiens (human)
peptide catabolic processAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of vasoconstrictionAngiotensin-converting enzyme Homo sapiens (human)
negative regulation of glucose importAngiotensin-converting enzyme Homo sapiens (human)
regulation of synaptic plasticityAngiotensin-converting enzyme Homo sapiens (human)
lung alveolus developmentAngiotensin-converting enzyme Homo sapiens (human)
amyloid-beta metabolic processAngiotensin-converting enzyme Homo sapiens (human)
arachidonic acid secretionAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of neurogenesisAngiotensin-converting enzyme Homo sapiens (human)
heart contractionAngiotensin-converting enzyme Homo sapiens (human)
regulation of angiotensin metabolic processAngiotensin-converting enzyme Homo sapiens (human)
hematopoietic stem cell differentiationAngiotensin-converting enzyme Homo sapiens (human)
angiogenesis involved in coronary vascular morphogenesisAngiotensin-converting enzyme Homo sapiens (human)
cellular response to glucose stimulusAngiotensin-converting enzyme Homo sapiens (human)
response to dexamethasoneAngiotensin-converting enzyme Homo sapiens (human)
cell proliferation in bone marrowAngiotensin-converting enzyme Homo sapiens (human)
regulation of heart rate by cardiac conductionAngiotensin-converting enzyme Homo sapiens (human)
negative regulation of calcium ion importAngiotensin-converting enzyme Homo sapiens (human)
response to thyroid hormoneAngiotensin-converting enzyme Homo sapiens (human)
blood vessel diameter maintenanceAngiotensin-converting enzyme Homo sapiens (human)
regulation of hematopoietic stem cell proliferationAngiotensin-converting enzyme Homo sapiens (human)
negative regulation of gap junction assemblyAngiotensin-converting enzyme Homo sapiens (human)
cellular response to aldosteroneAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of peptidyl-cysteine S-nitrosylationAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of systemic arterial blood pressureAngiotensin-converting enzyme Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
endopeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
carboxypeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
metalloendopeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
calmodulin bindingAngiotensin-converting enzyme Homo sapiens (human)
peptidase activityAngiotensin-converting enzyme Homo sapiens (human)
metallopeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
exopeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
tripeptidyl-peptidase activityAngiotensin-converting enzyme Homo sapiens (human)
peptidyl-dipeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
zinc ion bindingAngiotensin-converting enzyme Homo sapiens (human)
chloride ion bindingAngiotensin-converting enzyme Homo sapiens (human)
mitogen-activated protein kinase kinase bindingAngiotensin-converting enzyme Homo sapiens (human)
bradykinin receptor bindingAngiotensin-converting enzyme Homo sapiens (human)
mitogen-activated protein kinase bindingAngiotensin-converting enzyme Homo sapiens (human)
metallodipeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
heterocyclic compound bindingAngiotensin-converting enzyme Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
extracellular spaceAngiotensin-converting enzyme Homo sapiens (human)
extracellular regionAngiotensin-converting enzyme Homo sapiens (human)
extracellular spaceAngiotensin-converting enzyme Homo sapiens (human)
lysosomeAngiotensin-converting enzyme Homo sapiens (human)
endosomeAngiotensin-converting enzyme Homo sapiens (human)
plasma membraneAngiotensin-converting enzyme Homo sapiens (human)
external side of plasma membraneAngiotensin-converting enzyme Homo sapiens (human)
basal plasma membraneAngiotensin-converting enzyme Homo sapiens (human)
brush border membraneAngiotensin-converting enzyme Homo sapiens (human)
extracellular exosomeAngiotensin-converting enzyme Homo sapiens (human)
sperm midpieceAngiotensin-converting enzyme Homo sapiens (human)
plasma membraneAngiotensin-converting enzyme Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID38860In vitro inhibitory activity against Angiotensin I converting enzyme1985Journal of medicinal chemistry, Nov, Volume: 28, Issue:11
Angiotensin converting enzyme inhibitors: structure-activity profile of 1-benzazepin-2-one derivatives.
AID182947In vivo inhibitory activity against Angiotensin I pressor response in normotensive rats after peroral administration1985Journal of medicinal chemistry, Nov, Volume: 28, Issue:11
Angiotensin converting enzyme inhibitors: structure-activity profile of 1-benzazepin-2-one derivatives.
AID174576Maximal changes in blood pressure recorded during the 4 day test period in spontaneous hypertensive rats, at 30 mg/kg peroral dose1985Journal of medicinal chemistry, Nov, Volume: 28, Issue:11
Angiotensin converting enzyme inhibitors: structure-activity profile of 1-benzazepin-2-one derivatives.
AID59369In vivo inhibitory activity against Angiotensin I pressor response in normotensive dog after peroral administration1985Journal of medicinal chemistry, Nov, Volume: 28, Issue:11
Angiotensin converting enzyme inhibitors: structure-activity profile of 1-benzazepin-2-one derivatives.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (45.00)18.7374
1990's11 (55.00)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (17.39%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other19 (82.61%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]