Page last updated: 2024-11-10

zofenoprilate

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

Description

zofenoprilate: RN given refers to ((1(R*),2alpha,4alpha)-isomer; RN for cpd without isomeric designation not avail 9/90 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

zofenoprilat : A proline derivative that is 4-(phenylsulfanyl)-L-proline in which the amine proton is replaced by a (2S)-2-methyl-3-sulfanylpropanoyl group. The active metabolite of zofenopril. [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]

Cross-References

ID SourceID
PubMed CID3034048
CHEMBL ID16332
CHEBI ID82602
SCHEMBL ID678738
MeSH IDM0180157

Synonyms (31)

Synonym
l-proline, 1-[(2s)-3-mercapto-2-methyl-1-oxopropyl]-4-(phenylthio)-, 4s
ZED ,
zofenoprilat
2EWB
zofenoprilate
DB08766
CHEMBL16332 ,
chebi:82602 ,
(2s,4s)-1-[(2s)-2-methyl-3-sulfanylpropanoyl]-4-phenylsulfanylpyrrolidine-2-carboxylic acid
75176-37-3
bdbm50018850
1-(3-mercapto-2-methyl-propionyl)-4-phenylsulfanyl-pyrrolidine-2-carboxylic acid
zofenoprilate [inn-french]
zofenoprilat [inn]
4g4wdk2ybs ,
zofenoprilatum
l-proline, 1-(3-mercapto-2-methyl-1-oxopropyl)-4-(phenylthio)-, (1(r*),2alpha,4alpha)-
unii-4g4wdk2ybs
zofenoprilatum [inn-latin]
l-proline,1-[(2s)-3-mercapto-2-methyl-1-oxopropyl]-4-(phenylthio)-, (4s)-
gtpl6463
SCHEMBL678738
l-proline, 1-(3-mercapto-2-methyl-1-oxopropyl)-4-(phenylthio)-, (1(r*),2.alpha.,4.alpha.)-
(4s)-1-[(2s)-2-methyl-3-sulfanylpropanoyl]-4-(phenylsulfanyl)-l-proline
DTXSID50231443
AC-32038
C21576
(2s,4s)-1-((s)-3-mercapto-2-methylpropanoyl)-4-(phenylthio)pyrrolidine-2-carboxylic acid
Q8073347
(2s,4s)-1-((s)-3-mercapto-2-methylpropanoyl)-4-(phenylthio)pyrrolidine-2-carboxylicacid
EX-A7844Q

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The quantitative structure-bioavailability relationship of 232 structurally diverse drugs was studied to evaluate the feasibility of constructing a predictive model for the human oral bioavailability of prospective new medicinal agents."( QSAR model for drug human oral bioavailability.
Topliss, JG; Yoshida, F, 2000
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (6)

RoleDescription
anticonvulsantA drug used to prevent seizures or reduce their severity.
apoptosis inhibitorAny substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
cardioprotective agentAny protective agent that is able to prevent damage to the heart.
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitorAn EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).
drug metabolitenull
vasodilator agentA drug used to cause dilation of the blood vessels.
[role 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]

Drug Classes (4)

ClassDescription
N-acyl-L-amino acidAny N-acylamino acid having L-configuration.
aryl sulfideAny organic sulfide in which the sulfur is attached to at least one aromatic group.
thiolAn organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety.
L-proline derivativeA proteinogenic amino acid derivative resulting from reaction of L-proline at the amino group or the carboxy group, or from the replacement of any hydrogen of L-proline by a heteroatom.
[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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Cytosol aminopeptidaseBos taurus (cattle)Ki0.80000.80000.80000.8000AID977610
Angiotensin-converting enzymeOryctolagus cuniculus (rabbit)Ki0.00040.00042.03378.6606AID37802
Angiotensin-converting enzymeRattus norvegicus (Norway rat)IC50 (µMol)0.00800.00090.33223.0300AID37962
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID27167Delta logD (logD6.5 - logD7.4)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID37802Inhibitory constant against rabbit lung Angiotensin I converting enzyme1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines.
AID29359Ionization constant (pKa)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID29813Oral bioavailability in human2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID28681Partition coefficient (logD6.5)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID37962In vitro inhibitory activity against angiotensin I converting enzyme of rats.1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines.
AID1345430Rat Angiotensin-converting enzyme (M2: Angiotensin-converting (ACE and ACE2))1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines.
AID1811Experimentally measured binding affinity data derived from PDB2006Biochemistry, Mar-14, Volume: 45, Issue:10
Metal ion substitution in the catalytic site greatly affects the binding of sulfhydryl-containing compounds to leucyl aminopeptidase.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2006Biochemistry, Mar-14, Volume: 45, Issue:10
Metal ion substitution in the catalytic site greatly affects the binding of sulfhydryl-containing compounds to leucyl aminopeptidase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (5.56)18.7374
1990's3 (16.67)18.2507
2000's8 (44.44)29.6817
2010's6 (33.33)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.97

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.97 (24.57)
Research Supply Index3.04 (2.92)
Research Growth Index5.01 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.97)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (5.26%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other18 (94.74%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]