Page last updated: 2024-11-12

r-138727

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Description

R-138727: an active metabolite of CS-747 (prasugrel, LY640315) and P2Y12 receptor inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10405534
CHEMBL ID3526431
CHEBI ID172573
SCHEMBL ID1166529
MeSH IDM0498545

Synonyms (31)

Synonym
CHEBI:172573
(2z)-2-[1-[2-cyclopropyl-1-(2-luorophenyl)-2-oxoethyl]-4-sulanylpiperidin-3-ylidene]acetic acid
r-138727
r 138727
(2z)-2-[1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene]acetic acid
gtpl1771
r138727 ,
239466-74-1
prasugrel metabolite
204204-73-9
acetic acid, 2-(1-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4-mercapto-3-piperidinylidene)-, (2z)-
(2z)-2-(1-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4-mercapto-3-piperidinylidene) acetic acid
FLN02B3F1J ,
r-138727 [mi]
SCHEMBL1166529
AKOS025149434
prasugrel metabolite r-138727
(z)-2-(1-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4-mercaptopiperidin-3-ylidene)acetic acid
DTXSID50439427
(2z)-{1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene}acetic acid
CHEMBL3526431
{1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene}acetic acid
unii-fln02b3f1j
prasugrel, r-138727 [mi]
Q27088504
prasugrel active metabolite
(2z)-{1-[(1rs)-2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4-sulfanylpiperidin-3-ylidene}ethanoic acid
(z)-2-(1-(2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4-mercaptopiperidin-3-ylidene)aceticacid
prasugrel metabolite r-
CS-0084173
HY-123669

Research Excerpts

Pharmacokinetics

Plasma concentration of its active metabolite, R-138727, and pharmacokinetic parameters were determined on days 1 and 7 after dosing.

ExcerptReferenceRelevance
"Serial pharmacokinetic (PK) sampling in 1159 patients from TRITON-TIMI 38 was undertaken."( Population pharmacokinetic analyses to evaluate the influence of intrinsic and extrinsic factors on exposure of prasugrel active metabolite in TRITON-TIMI 38.
Antman, EM; Braunwald, E; Ernest, CS; Li, YG; Macias, WL; Ni, L; Riesmeyer, JR; Rohatagi, S; Salazar, DE; Small, DS; Weerakkody, GJ; Wiviott, SD; Wrishko, RE, 2009
)
0.35
"An integrated analysis of pharmacokinetic (PK) parameter estimates for prasugrel, from 16 phase I clinical pharmacology studies, consolidated exposure estimates from 506 healthy male and female participants and evaluated the effect of specific intrinsic and extrinsic factors on exposure to prasugrel's active metabolite (AM, R-138727)."( Integrated analysis of pharmacokinetic data across multiple clinical pharmacology studies of prasugrel, a new thienopyridine antiplatelet agent.
April, JH; Ernest, CS; Farid, NA; Li, YG; Ni, L; Payne, CD; Rohatagi, S; Small, DS; Winters, KJ, 2011
)
0.54
" We assessed the pharmacokinetic and pharmacodynamic effects of prasugrel at the clinical dose used in Japan in healthy Japanese elderly subjects compared with non-elderly subjects."( Evaluation of the Pharmacokinetics and Pharmacodynamics of Prasugrel in Japanese Elderly Subjects.
Fukase, H; Hasunuma, T; Miyazaki, A; Nishikawa, Y, 2017
)
0.46
" Plasma concentration of its active metabolite, R-138727, and pharmacokinetic parameters were determined on days 1 and 7 after dosing."( Evaluation of the Pharmacokinetics and Pharmacodynamics of Prasugrel in Japanese Elderly Subjects.
Fukase, H; Hasunuma, T; Miyazaki, A; Nishikawa, Y, 2017
)
0.71
" There was no statistically significant difference in pharmacokinetic parameters between groups: area under the plasma concentration-time curve up to the last quantifiable time and maximum plasma concentration were about 174-175 ng·h/mL and 134-153 ng/mL, respectively, after the loading dose; and about 25-26 ng·h/mL and 25 ng/mL, respectively, after the maintenance dose."( Evaluation of the Pharmacokinetics and Pharmacodynamics of Prasugrel in Japanese Elderly Subjects.
Fukase, H; Hasunuma, T; Miyazaki, A; Nishikawa, Y, 2017
)
0.46

Compound-Compound Interactions

ExcerptReferenceRelevance
"We evaluated the pharmacokinetics and pharmacodynamics of prasugrel used in combination with aspirin in healthy Japanese subjects."( Platelet Aggregation Inhibitory Effects and Pharmacokinetics of Prasugrel Used in Combination With Aspirin in Healthy Japanese Subjects.
Ikeda, Y; Kondo, K; Matsushima, N; Umemura, K, 2017
)
0.46

Bioavailability

ExcerptReferenceRelevance
" The relative bioavailability of the active metabolites of prasugrel and clopidogrel calculated by the ratio of active metabolite AUC (prodrug oral administration/active metabolite intravenous administration) were 25% and 7%, respectively, in rats, and 25% and 10%, respectively, in dogs."( Comparison of formation of thiolactones and active metabolites of prasugrel and clopidogrel in rats and dogs.
Farid, NA; Fusegawa, K; Hagihara, K; Ikeda, T; Ikenaga, H; Kazui, M; Kurihara, A; Nanba, T; Okazaki, O; Takahashi, M, 2009
)
0.35

Dosage Studied

ExcerptRelevanceReference
" The steady-state trough MPA to ADP 20 micromol/L during 10-mg maintenance dosing was 30."( Effect of age on the pharmacokinetics and pharmacodynamics of prasugrel during multiple dosing: an open-label, single-sequence, clinical trial.
Ernest, CS; Farid, NA; Li, YG; Ni, L; Payne, CD; Salazar, DE; Small, DS; Winters, KJ; Wrishko, RE, 2009
)
0.35
" These results characterize prasugrel's PK across a range of studies and highlight body weight as the most influential covariate on prasugrel AM exposure, with implications for prasugrel maintenance dosing in clinical practice."( Integrated analysis of pharmacokinetic data across multiple clinical pharmacology studies of prasugrel, a new thienopyridine antiplatelet agent.
April, JH; Ernest, CS; Farid, NA; Li, YG; Ni, L; Payne, CD; Rohatagi, S; Small, DS; Winters, KJ, 2011
)
0.37
" Although there was no effect on the patency rate before R-138727 dosing (P=0."( The active metabolite of prasugrel, R-138727, improves cerebral blood flow and reduces cerebral infarction and neurologic deficits in a non-human primate model of acute ischaemic stroke.
Jakubowski, JA; Mizuno, M; Ohno, K; Sugidachi, A; Tomizawa, A, 2016
)
0.95
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
organofluorine compoundAn organofluorine compound is a compound containing at least one carbon-fluorine bond.
[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]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1215196AUC (0 to 2 hrs) in beagle dog treated with 1 mg/kg, hepatic vein prasugrel2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
The intestine as an important contributor to prasugrel active metabolite formation in vivo.
AID1215199Drug level in human intestinal S9 fraction treated with 250 uM prasugrel upto 60 mins incubation2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
The intestine as an important contributor to prasugrel active metabolite formation in vivo.
AID1215106Drug metabolism in potassium phosphate buffer treated with R-133490 at 1 uM after 1 to 10 mins by LC-MS/MS analysis in presence of human liver cytosol and glutathione2011Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 39, Issue:2
Glutaredoxin and thioredoxin can be involved in producing the pharmacologically active metabolite of a thienopyridine antiplatelet agent, prasugrel.
AID1215118Drug metabolism in human liver cytosol treated with R-133490 at 0.1 to 0.05 mM after 5 mins by HPLC analysis in presence of dithiothreitol and 67 ug/ml anti-human thioredoxin antibody2011Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 39, Issue:2
Glutaredoxin and thioredoxin can be involved in producing the pharmacologically active metabolite of a thienopyridine antiplatelet agent, prasugrel.
AID1215107Drug metabolism in human liver microsomes treated with R-133490 at 1 uM after 1 to 10 mins by LC-MS/MS analysis in presence of human liver cytosol and glutathione2011Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 39, Issue:2
Glutaredoxin and thioredoxin can be involved in producing the pharmacologically active metabolite of a thienopyridine antiplatelet agent, prasugrel.
AID1215195AUC (0 to 2 hrs) in beagle dog treated with 1 mg/kg, portal vein prasugrel2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
The intestine as an important contributor to prasugrel active metabolite formation in vivo.
AID1215197AUC (0 to 2 hrs) in beagle dog treated with 1 mg/kg, systemic vein prasugrel2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
The intestine as an important contributor to prasugrel active metabolite formation in vivo.
AID1215198Drug level in dog intestinal S9 fraction treated with 250 uM prasugrel upto 60 mins incubation2011Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 39, Issue:4
The intestine as an important contributor to prasugrel active metabolite formation in vivo.
AID1215108Drug metabolism in potassium phosphate buffer treated with R-133490 at 1 uM after 1 to 10 mins by LC-MS/MS analysis2011Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 39, Issue:2
Glutaredoxin and thioredoxin can be involved in producing the pharmacologically active metabolite of a thienopyridine antiplatelet agent, prasugrel.
AID1346320Human P2Y12 receptor (P2Y receptors)2005Thrombosis and haemostasis, Sep, Volume: 94, Issue:3
Stereoselective inhibition of human platelet aggregation by R-138727, the active metabolite of CS-747 (prasugrel, LY640315), a novel P2Y12 receptor inhibitor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (32)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's12 (37.50)29.6817
2010's20 (62.50)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: 10.82

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 Index10.82 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.82)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (21.88%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other25 (78.13%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]