Page last updated: 2024-11-13

2-oxo-clopidogrel

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

Description

2-oxo-clopidogrel: metabolite of clopidogrel [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID56848893
CHEMBL ID2042272
SCHEMBL ID10021031
MeSH IDM0536054

Synonyms (43)

Synonym
2-oxo-clopidogrel
thieno(3,2-c)pyridine-5(4h)-acetic acid, alpha-(2-chlorophenyl)-2,6,7,7a-tetrahydro-2-oxo-, methyl ester, (alphas)-
2-oxoclopidogrel
CHEMBL2042272
clopidogrel thiolactone
CS-4888
(2s)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3.2-c]pyridin-5(2h, 4h, 6h)-yl)-acetate
JBSAZVIMJUOBNB-WUJWULDRSA-N
(2s)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3,2-c]pyridin-5 (2h,4h, 6h)-yl)-acetate
(2s)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3.2-c]pyridine-5(2h,4h,6h)-yl)-acetate
(2s)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7, 7a-dihydrothieno[3,2-c]pyridin-5(2h,4h,6h)-yl)-acetate
(2s)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3,2-c]pyridine-5(2h,4h, 6h)-yl)-acetate
(2s)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3.2-c]pyridine-5(2h, 4h, 6h)-yl)-acetate
(2s)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3,2-c]pyridin-5(2h,4h,6h)-yl)-acetate
(2s)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3.2-c]pyridin-5 (2h,4h, 6h)-yl)-acetate
(2s)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3.2-c]pyridin-5(2h,4h,6h)-yl)-acetate
AKOS016844921
1147350-75-1
SCHEMBL10021031
(2s)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7, 7a-dihydrothieno(3,2-c)pyridin-5(2h,4h,6h)-yl)-acetate
(.alpha.s)-.alpha.-(2,4,5,6,7,7a-hexahydro-2-oxothieno(3,2-c)pyridine 5-yl)-2-chlorobenzeneacetic acid methyl ester
methyl (2s)-2-(2-chlorophenyl)-2-(2-oxo-4,6,7,7a-tetrahydrothieno(3,2-c)pyridin-5-yl)acetate
thieno(3,2-c)pyridine-5(4h)-acetic acid, .alpha.-(2-chlorophenyl)-2,6,7,7a-tetrahydro-2-oxo-, methyl ester, (.alpha.s)-
methyl (2s)-(2-chlorophenyl)(2-oxo-2,6,7,7a-tetrahydrothieno(3,2-c)pyridin-5(4h)-yl)acetate
(7s)-sr121683
j3.292.123j ,
sr-121683
0IX303KU54 ,
(alphas)-alpha-(2,4,5,6,7,7a-hexahydro-2-oxothieno(3,2-c)pyridine 5-yl)-2-chlorobenzeneacetic acid methyl ester
unii-0ix303ku54
(2s)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3,2-c]pyridin-5(2h,4h,6h)-yl)acetate
HY-15876
methyl (2s)-2-(2-chlorophenyl)-2-{2-oxo-2h,4h,5h,6h,7h,7ah-thieno[3,2-c]pyridin-5-yl}acetate
methyl (2s)-(2-chlorophenyl)(2-oxo-2,6,7,7a-tetrahydrothieno[3,2-c]pyridin-5(4h)-yl)acetate
DTXSID00718734
NCGC00484086-01
methyl (2s)-2-(2-chlorophenyl)-2-(2-oxo-2,6,7,7a-tetrahydrothieno[3,2-c]pyridin-5(4h)-yl)acetate
thieno[3,2-c]pyridine-5(4h)-acetic acid, alpha-(2-chlorophenyl)-2,6,7,7a-tetrahydro-2-oxo-, methyl ester, (alphas)-
Q27236838
methyl (2s)-2-(2-chlorophenyl)-2-(2-oxo-4,6,7,7a-tetrahydrothieno[3,2-c]pyridin-5-yl)acetate
F85263
MS-25134
XVB35075

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" In the present study, a dynamic physiologically based pharmacokinetic (PBPK) model was developed in Simcyp for clopidogrel and clopi-H4 using a specific sequential metabolite module in four populations with phenotypically different CYP2C19 activity (poor, intermediate, extensive, and ultrarapid metabolizers) receiving a loading dose of 300 mg followed by a maintenance dose of 75 mg."( Physiologically based pharmacokinetic modeling for sequential metabolism: effect of CYP2C19 genetic polymorphism on clopidogrel and clopidogrel active metabolite pharmacokinetics.
Boulenc, X; Djebli, N; Fabre, D; Fabre, G; Hurbin, F; Sultan, E, 2015
)
0.42

Compound-Compound Interactions

ExcerptReferenceRelevance
" Accordingly, potential drug-drug interactions associated with the concomitant use of these agents present an area of concern."( Carboxylesterase 1-mediated drug-drug interactions between clopidogrel and simvastatin.
Markowitz, JS; Wang, X; Zhu, HJ, 2015
)
0.42

Bioavailability

ExcerptReferenceRelevance
" Preliminary pharmacokinetic study results showed that the bioavailability of clopidogrel thiolactone generated from 9a was 6-fold higher than that generated from clopidogrel, implying a much lower clinically effective dose for 9a in comparison with clopidogrel."( Overcoming clopidogrel resistance: discovery of vicagrel as a highly potent and orally bioavailable antiplatelet agent.
Gong, Y; Jiao, B; Lv, F; Qi, X; Shan, J; Sun, H; Yuan, F; Zhang, B; Zheng, W; Zhu, Y, 2012
)
0.38
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" Additionally, CES1 genetic variants have the potential to serve as a biomarker to predict clopidogrel response and individualize clopidogrel dosing regimens in clinical practice."( Carboxylesterase 1 as a determinant of clopidogrel metabolism and activation.
Angiolillo, DJ; Brinda, BJ; Gawronski, BE; Markowitz, JS; Wang, X; Zhu, HJ, 2013
)
0.39
" Therefore, the ABCB1 C3435T genotyping should be one of the parameters taken into account when deciding about the dosing regimen of clopidogrel."( P-Glycoprotein Polymorphism C3435T Is Associated with Dose-Adjusted Clopidogrel and 2-Oxo-Clopidogrel Concentration.
Apostolovic, SR; Jankovic, SM; Jevtovic-Stoimenov, T; Konstantinovic, SS; Lilic, J; Nikolic, VN; Pavlovic, M; Stokanovic, D; Zivkovic, VS; Zvezdanovic, JB, 2016
)
0.66
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pathways (2)

PathwayProteinsCompounds
Clopidogrel Action Pathway98
Clopidogrel Metabolism Pathway98

Bioassays (9)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1211557Drug metabolism in human liver microsome assessed as (2S)-2-amino-5-((2R)-1-(carboxymethylamino)-3-(((E)-3-(carboxymethylene)-1-((S)-1-(2-chlorophenyl)-2-methoxy-2-oxoethyl)piperidin-4-yl)disulfanyl)-1-oxopropan-2-ylamino)-5-oxopentanoic acid formation at2012Drug metabolism and disposition: the biological fate of chemicals, Sep, Volume: 40, Issue:9
Glutaredoxin is involved in the formation of the pharmacologically active metabolite of clopidogrel from its GSH conjugate.
AID667513Antiplatelet activity in Wistar rat assessed as inhibition of ADP-induced platelet aggregation at 3 mg/kg, po measured after 2 hrs by Born's method2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Overcoming clopidogrel resistance: discovery of vicagrel as a highly potent and orally bioavailable antiplatelet agent.
AID1211560Drug metabolism in human liver microsome assessed as (2S)-2-amino-5-((2R)-1-(carboxymethylamino)-3-(((E)-3-(carboxymethylene)-1-((S)-1-(2-chlorophenyl)-2-methoxy-2-oxoethyl)piperidin-4-yl)disulfanyl)-1-oxopropan-2-ylamino)-5-oxopentanoic acid formation at2012Drug metabolism and disposition: the biological fate of chemicals, Sep, Volume: 40, Issue:9
Glutaredoxin is involved in the formation of the pharmacologically active metabolite of clopidogrel from its GSH conjugate.
AID1211558Drug metabolism in human liver microsome assessed as (E)-2-(1-((S)-1-(2-chlorophenyl)-2-methoxy-2-oxoethyl)-4-mercaptopiperidin-3-ylidene)acetic acid formation at 5 uM by LC-MS/MS analysis in presence of 5 mM GSH2012Drug metabolism and disposition: the biological fate of chemicals, Sep, Volume: 40, Issue:9
Glutaredoxin is involved in the formation of the pharmacologically active metabolite of clopidogrel from its GSH conjugate.
[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-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (5.00)29.6817
2010's17 (85.00)24.3611
2020's2 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.12

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index24.12 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index5.62 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.12)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (10.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other18 (90.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]