Page last updated: 2024-12-06

ceronapril

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

Description

ceronapril: structure given in first source; RN given for (S)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID189729
CHEMBL ID36503
CHEBI ID177391
SCHEMBL ID121163
MeSH IDM0153898

Synonyms (39)

Synonym
(2s)-1-[(2s)-6-amino-2-[hydroxy(4-phenylbutyl)phosphoryl]oxyhexanoyl]pyrrolidine-2-carboxylic acid
CHEBI:177391
ceronapril
novopril
sq-29852
D03440
ceronapril (usan/inn)
111223-26-8
(s)-1-(6-amino-2-((hydroxy(4-phenylbutyl)phosphinyl)oxy)-1-oxohexyl)-l-proline
ceronapril [usan:inn]
l-proline, 1-(6-amino-2-((hydroxy(4-phenylbutyl)phosphinyl)oxy)-1-oxohexyl)-, (s)-
brn 3635091
sq 29852
ceronaprilum [inn-latin]
1-((2s)-6-amino-2-hydroxyhexanoyl)-l-proline, hydrogen (4-phenylbutyl)phosphonate (ester)
CHEMBL36503 ,
sq 29,852
120122-26-1
A19756
2,6-difluoro-4-iodo-phenylamine
unii-x3mm60sovp
ceronaprilum
x3mm60sovp ,
bdbm50405594
sq29,852
SCHEMBL121163
ceronapril [jan]
ceronapril [usan]
ceronapril [inn]
ceronapril [who-dd]
ceronapril [mart.]
ceronapril [mi]
ceronapril; sq 29852
DTXSID80891418
Q27293516
((2s)-6-amino-2-((hydroxy(4-phenylbutyl)phosphoryl)oxy)hexanoyl)-l-proline
CS-0026611
HY-106816
AKOS040746686

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Compound 2 is well absorbed from rat jejunum, whereas lisinopril absorption is relatively low."( Intestinal absorption mechanism of dipeptide angiotensin converting enzyme inhibitors of the lysyl-proline type: lisinopril and SQ 29,852.
Amidon, GL; Friedman, DI, 1989
)
0.28

Dosage Studied

ExcerptRelevanceReference
" Clinical samples from the ascending dosage studies have been analyzed by the ceronapril RIA."( Radioimmunoassay for ceronapril, a new angiotensin-converting enzyme inhibitor, and its application to a pharmacokinetic study in healthy male volunteers.
Brennan, J; Mantha, S; Stouffer, B; Tsay, HM; Tu, JI; Turabi, N, 1992
)
0.28
" In ex vivo dose-response and time-course studies, the inhibitory effects of the seven drugs on tissue ACEs and their relative distributions to SHR tissues were compared following oral administration."( Comparisons in vitro, ex vivo, and in vivo of the actions of seven structurally diverse inhibitors of angiotensin converting enzyme (ACE).
Cushman, DW; DeForrest, JM; Fung, WC; Grover, GJ; Harvey, CM; Mitch, SL; Scalese, RJ; Wang, FL, 1989
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-acyl-amino acidA carboxamide resulting from the formal condensation of a carboxylic acid with the amino group of an amino acid.
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Angiotensin-converting enzyme Homo sapiens (human)IC50 (µMol)0.03630.00010.533610.0000AID39018
Angiotensin-converting enzymeOryctolagus cuniculus (rabbit)IC50 (µMol)0.03600.00001.612910.0000AID37643
[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 (8)

Assay IDTitleYearJournalArticle
AID39018Inhibitory activity against angiotensin converting enzyme (ACE)1993Journal of medicinal chemistry, Aug-06, Volume: 36, Issue:16
Three-dimensional quantitative structure-activity relationship of angiotesin-converting enzyme and thermolysin inhibitors. II. A comparison of CoMFA models incorporating molecular orbital fields and desolvation free energies based on active-analog and com
AID37646In vitro inhibition of angiotensin I converting enzyme in rabbit lung with hippuryl-histidyl-leucine as substrate1988Journal of medicinal chemistry, Jan, Volume: 31, Issue:1
(Phosphinyloxy)acyl amino acid inhibitors of angiotensin converting enzyme (ACE). 1. Discovery of (S)-1-[6-amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]-L -proline a novel orally active inhibitor of ACE.
AID177501In vivo inhibition of angiotensin I induced pressor effect after po administration in rats1988Journal of medicinal chemistry, Jan, Volume: 31, Issue:1
(Phosphinyloxy)acyl amino acid inhibitors of angiotensin converting enzyme (ACE). 1. Discovery of (S)-1-[6-amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]-L -proline a novel orally active inhibitor of ACE.
AID177147In vivo dose required to produce 50% inhibition against angiotensin I in normotensive rat after intravenous administration1990Journal of medicinal chemistry, May, Volume: 33, Issue:5
(Phosphinyloxy)acyl amino acid inhibitors of angiotensin converting enzyme. 2. Terminal amino acid analogues of (S)-1-[6-amino-2 [[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]-L-proline.
AID37643Inhibition of rabbit lung angiotensin I converting enzyme (ACE) using hippuryl-histidyl-leucine as substrate1990Journal of medicinal chemistry, May, Volume: 33, Issue:5
(Phosphinyloxy)acyl amino acid inhibitors of angiotensin converting enzyme. 2. Terminal amino acid analogues of (S)-1-[6-amino-2 [[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]-L-proline.
AID177500In vivo inhibition of angiotensin I induced pressor effect after iv administration in rats1988Journal of medicinal chemistry, Jan, Volume: 31, Issue:1
(Phosphinyloxy)acyl amino acid inhibitors of angiotensin converting enzyme (ACE). 1. Discovery of (S)-1-[6-amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]-L -proline a novel orally active inhibitor of ACE.
AID183703In vivo oral activity in normotensive rat and percent maximal inhibition of the angiotensin I pressor response1990Journal of medicinal chemistry, May, Volume: 33, Issue:5
(Phosphinyloxy)acyl amino acid inhibitors of angiotensin converting enzyme. 2. Terminal amino acid analogues of (S)-1-[6-amino-2 [[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]-L-proline.
AID181898In vivo inhibition angiotensin I induced pressor effect after (5 uML/kg) p.o. administration in rats1988Journal of medicinal chemistry, Jan, Volume: 31, Issue:1
(Phosphinyloxy)acyl amino acid inhibitors of angiotensin converting enzyme (ACE). 1. Discovery of (S)-1-[6-amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]-L -proline a novel orally active inhibitor of ACE.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (43)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (11.63)18.7374
1990's35 (81.40)18.2507
2000's3 (6.98)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 (%)
Trials3 (6.67%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other42 (93.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]