Page last updated: 2024-11-08

temocaprilat

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

Description

temocaprilat: the diacid of temocapril; active metabolite of angiotensin converting enzyme inhibitor (CS-622); RN refers to (2S-(2alpha,6beta(R*))) isomer; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID443151
CHEMBL ID300841
CHEBI ID9436
SCHEMBL ID498916
MeSH IDM0188837

Synonyms (31)

Synonym
rs-5139
110221-53-9
temocaprilat
rnh-5139
chebi:9436 ,
temocapril diacid
CHEMBL300841 ,
(2s)-2-[[(2s,6r)-4-(carboxymethyl)-5-oxo-2-thiophen-2-yl-1,4-thiazepan-6-yl]amino]-4-phenylbutanoic acid
bdbm50024710
AKOS016010295
temocaprilat [inn:ban]
(+)-(2s,6r)-6-(((1s)-1-carboxy-3-phenylpropyl)amino)tetrahydro-5-oxo-2-(2-thienyl)-1,4-thiazepine-4(5h)-acetic acid
rnh 5139
2d6a12q12r ,
unii-2d6a12q12r
1,4-thiazepine-4(5h)-acetic acid, 6-((1-carboxy-3-phenylpropyl)amino)tetrahydro-5-oxo-2-(2-thienyl)-, (2s-(2alpha,6beta(r*)))-
temocaprilat [who-dd]
temocapril diacid [mi]
temocaprilat [inn]
1,4-thiazepine-4(5h)-acetic acid, 6-((1-carboxy-3-phenylpropyl)amino)tetrahydro-5-oxo-2-(2-thienyl)-, (2s- (2.alpha.,6.beta.(r*)))-
SCHEMBL498916
J-002404
(2s)-2-{[(2s,6r)-4-(carboxymethyl)-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-6-yl]amino}-4-phenylbutanoic acid
DTXSID60891350
(s)-2-(((2s,6r)-4-(carboxymethyl)-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-6-yl)amino)-4-phenylbutanoic acid
Q27108393
C90365
compound 24c [pmid: 3669006]
gtpl11737
CS-0014046
HY-A0117

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"For temocapril, there were no statistically significant differences in median tmax or mean Cmax, AUC(SS), t1/2,Z, CL/F between the four groups."( Pharmacokinetics of temocapril and temocaprilat after 14 once daily oral doses of temocapril in hypertensive patients with varying degrees of renal impairment.
Eckl, KM; Fritsche, L; Lavrijssen, AT; Neumayer, HH; Püchler, K; Renneisen, K; Roots, I; Sierakowski, B; Thomsen, T, 1997
)
0.57
" Pharmacokinetic profiles were determined after the single and the last dose."( Single dose and steady state pharmacokinetics of temocapril and temocaprilat in young and elderly hypertensive patients.
Püchler, K; Roots, I; Sierakowski, B, 1998
)
0.54
" All other pharmacokinetic parameters for temocapril and temocaprilat did not show any significant difference."( Single dose and steady state pharmacokinetics of temocapril and temocaprilat in young and elderly hypertensive patients.
Püchler, K; Roots, I; Sierakowski, B, 1998
)
0.78
"The pharmacokinetic differences detected in the elderly do not require a dose adjustment per se."( Single dose and steady state pharmacokinetics of temocapril and temocaprilat in young and elderly hypertensive patients.
Püchler, K; Roots, I; Sierakowski, B, 1998
)
0.54

Compound-Compound Interactions

ExcerptReferenceRelevance
" Although the participation of the particular transporters in observed drug-drug interactions can be difficult to confirm in humans, this review focuses mainly on pharmacokinetic interactions of clinically important drugs."( Transporter-mediated Drug Interactions.
Tsuji, A, 2002
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
non-proteinogenic alpha-amino acidAny alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
[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]

Pathways (2)

PathwayProteinsCompounds
Temocapril Metabolism Pathway02
Temocapril Action Pathway34

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Angiotensin-converting enzymeOryctolagus cuniculus (rabbit)IC50 (µMol)0.00360.00001.612910.0000AID37671
Canalicular multispecific organic anion transporter 1Rattus norvegicus (Norway rat)Ki343.00000.84004.968210.0000AID679037
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Solute carrier organic anion transporter family member 1A1Rattus norvegicus (Norway rat)Km46.70000.01503.49967.0000AID679964
Canalicular multispecific organic anion transporter 1Rattus norvegicus (Norway rat)Km92.50001.50004.34206.9000AID679014
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1222129Partition coefficient, log P between n-octanol and phosphate buffer at pH 7.42011Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 39, Issue:7
Prediction of human intestinal absorption of the prodrug temocapril by in situ single-pass perfusion using rat intestine with modified hydrolase activity.
AID1222147Drug uptake in Wistar rat jejunum blood vessel assessed as rate of drug appearance at 100 uM by in-situ single-pass perfusion method2011Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 39, Issue:7
Prediction of human intestinal absorption of the prodrug temocapril by in situ single-pass perfusion using rat intestine with modified hydrolase activity.
AID681152TP_TRANSPORTER: uptake in Xenopus laevis oocytes2002Drug metabolism and pharmacokinetics, , Volume: 17, Issue:4
Transporter-mediated Drug Interactions.
AID37671Inhibitory activity against rabbit lung Angiotensin I converting enzyme with 5 mM hippuryl-histidyl-leucine as substrate1987Journal of medicinal chemistry, Nov, Volume: 30, Issue:11
Angiotensin-converting enzyme inhibitors: perhydro-1,4-thiazepin-5-one derivatives.
AID1222148Drug uptake in Wistar rat jejunum lumen assessed as rate of drug appearance at 100 uM by in-situ single-pass perfusion method2011Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 39, Issue:7
Prediction of human intestinal absorption of the prodrug temocapril by in situ single-pass perfusion using rat intestine with modified hydrolase activity.
AID679581TP_TRANSPORTER: inhibition of Digoxin transepithelial transport (basal to apical)(Digoxin: 0.1 uM, Temocaprilat: 50 uM) in MDR1-expressing LLC-PK1 cells2002Life sciences, Feb-15, Volume: 70, Issue:13
Interaction of digoxin with antihypertensive drugs via MDR1.
AID1222144Drug uptake in Wistar rat jejunum blood vessel assessed as rate of drug appearance at 100 uM at pH 6.4 by in-situ single-pass perfusion method2011Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 39, Issue:7
Prediction of human intestinal absorption of the prodrug temocapril by in situ single-pass perfusion using rat intestine with modified hydrolase activity.
AID679964TP_TRANSPORTER: uptake in Oatp1-expressing COS-7 cells1998The Journal of pharmacology and experimental therapeutics, Oct, Volume: 287, Issue:1
Transport of temocaprilat into rat hepatocytes: role of organic anion transporting polypeptide.
AID679037TP_TRANSPORTER: inhibition of DNP-SG uptake in bile canalicular membrane vesicles from SD rat1997The Journal of pharmacology and experimental therapeutics, Mar, Volume: 280, Issue:3
Temocaprilat, a novel angiotensin-converting enzyme inhibitor, is excreted in bile via an ATP-dependent active transporter (cMOAT) that is deficient in Eisai hyperbilirubinemic mutant rats (EHBR).
AID1222133Apparent absorption clearance in Wistar rat jejunum at 100 uM at pH 6.4 by in-situ single-pass perfusion method2011Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 39, Issue:7
Prediction of human intestinal absorption of the prodrug temocapril by in situ single-pass perfusion using rat intestine with modified hydrolase activity.
AID1222139Intracellular drug level in Wistar rat jejunum at 100 uM at pH 6.4 by in-situ single-pass perfusion method2011Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 39, Issue:7
Prediction of human intestinal absorption of the prodrug temocapril by in situ single-pass perfusion using rat intestine with modified hydrolase activity.
AID679014TP_TRANSPORTER: uptake in bile canalicular membrane vesicles from SD rat1997The Journal of pharmacology and experimental therapeutics, Mar, Volume: 280, Issue:3
Temocaprilat, a novel angiotensin-converting enzyme inhibitor, is excreted in bile via an ATP-dependent active transporter (cMOAT) that is deficient in Eisai hyperbilirubinemic mutant rats (EHBR).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (3.45)18.7374
1990's7 (24.14)18.2507
2000's19 (65.52)29.6817
2010's2 (6.90)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 (13.79%)5.53%
Reviews1 (3.45%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (82.76%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]