Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C20H20FNO3S.C4H4O4 |
| Molecular Weight | 489.513 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C/C(O)=O.CC(=O)OC1=CC2=C(CCN(C2)C(C(=O)C3CC3)C4=C(F)C=CC=C4)S1
InChI
InChIKey=YFTPSWAPYMNPMX-BTJKTKAUSA-N
InChI=1S/C20H20FNO3S.C4H4O4/c1-12(23)25-18-10-14-11-22(9-8-17(14)26-18)19(20(24)13-6-7-13)15-4-2-3-5-16(15)21;5-3(6)1-2-4(7)8/h2-5,10,13,19H,6-9,11H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
| Molecular Formula | C20H20FNO3S |
| Molecular Weight | 373.441 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| Molecular Formula | C4H4O4 |
| Molecular Weight | 116.0722 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB06209Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022307s002lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB06209
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022307s002lbl.pdf
Prasugrel, a thienopyridine derivative, is a platelet activation and aggregation inhibitor structurally and pharmacologically related to clopidogrel and ticlopidine. Similar to clopidogrel, prasugrel is a prodrug that requires enzymatic transformation in the liver to its active metabolite, R-138727. R-138727 irreversibly binds to P2Y12 type ADP receptors on platelets thus preventing activation of the GPIIb/IIIa receptor complex. As a result, inhibition of ADP-mediated platelet activation and aggregation occurs. Prasugrel was developed by Daiichi Sankyo Co. and is currently marketed under the brand name EFFIENT in the United States and Canada in cooperation with Eli Lilly and Company for acute coronary syndromes planned for percutaneous coronary intervention (PCI). FDA approved in 2009.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0070527 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | EFFIENT Approved UseAcute Coronary Syndrome
Effient is indicated to reduce the rate of thrombotic cardiovascular (CV) events (including stent thrombosis) in patients with acute coronary syndrome (ACS) who are to be managed with percutaneous coronary intervention (PCI) as follows:
• Patients with unstable angina (UA) or non-ST-elevation myocardial infarction (NSTEMI).
• Patients with ST-elevation myocardial infarction (STEMI) when managed with primary or delayed PCI. Launch Date1.24709765E12 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
153.3 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28417436 |
20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
R-138727 blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
163.2 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27474356 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
R-138727 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
178.8 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28417436 |
20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
R-138727 blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
163 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27474356 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
R-138727 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28417436 |
20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
R-138727 blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.2 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27474356 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
R-138727 plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
healthy, 18–50 years n = 6 Health Status: healthy Age Group: 18–50 years Sex: M Population Size: 6 Sources: |
Other AEs: Alanine aminotransferase increased... Other AEs: Alanine aminotransferase increased (2 patients) Sources: |
75 mg single, oral Highest studied dose |
healthy, 30.4 years (range: 19.0–48.0 years) n = 5 Health Status: healthy Age Group: 30.4 years (range: 19.0–48.0 years) Sex: M Population Size: 5 Sources: |
Other AEs: Dizziness... |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, ≥ 75 years Health Status: unhealthy Age Group: ≥ 75 years Sources: |
Disc. AE: Bleeding... AEs leading to discontinuation/dose reduction: Bleeding (grade 5|severe) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Alanine aminotransferase increased | 2 patients | 20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
healthy, 18–50 years n = 6 Health Status: healthy Age Group: 18–50 years Sex: M Population Size: 6 Sources: |
| Dizziness | 1 patient | 75 mg single, oral Highest studied dose |
healthy, 30.4 years (range: 19.0–48.0 years) n = 5 Health Status: healthy Age Group: 30.4 years (range: 19.0–48.0 years) Sex: M Population Size: 5 Sources: |
| Bleeding | grade 5|severe Disc. AE |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, ≥ 75 years Health Status: unhealthy Age Group: ≥ 75 years Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| unlikely | ||||
| unlikely | ||||
| unlikely | ||||
| unlikely | ||||
| unlikely | ||||
| unlikely | ||||
| unlikely | ||||
| weak | weak (co-administration study) Comment: prasugrel decreased exposure to hydroxybupropion, a CYP2B6-mediated metabolite of bupropion, by 23% Page: 13.0 |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| major | no (co-administration study) Comment: administration with rifampicin (CYP2B6 inducer) did not significantly change its inhibtion of platelet aggregation Page: 12.0 |
|||
| major | no (co-administration study) Comment: administration with ketoconazole (inhibitor) and atorvastatin (CYP3A4 substrate) did not affect prasugrel-mediated inhibition of platelet aggregation Page: 12.0 |
|||
| minor | no (co-administration study) Comment: administration with rifampicin (CYP2C19 inducer) did not significantly change its inhibtion of platelet aggregation Page: 12.0 |
|||
| minor | no (co-administration study) Comment: administration with rifampicin (CYP2C9 inducer) did not significantly change its inhibtion of platelet aggregation Page: 12.0 |
|||
| no | no (pharmacogenomic study) Comment: There is no relevant effect of genetic variation on the pharmacokinetics of prasugrel’s active metabolite or its inhibition of platelet aggregation Page: 13.0 |
|||
| no | no (pharmacogenomic study) Comment: There is no relevant effect of genetic variation on the pharmacokinetics of prasugrel’s active metabolite or its inhibition of platelet aggregation Page: 13.0 |
|||
| no | no (pharmacogenomic study) Comment: There is no relevant effect of genetic variation on the pharmacokinetics of prasugrel’s active metabolite or its inhibition of platelet aggregation Page: 13.0 |
|||
| no | no (pharmacogenomic study) Comment: There is no relevant effect of genetic variation on the pharmacokinetics of prasugrel’s active metabolite or its inhibition of platelet aggregation Page: 13.0 |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| The influence of P2Y12 receptor deficiency on the platelet inhibitory activities of prasugrel in a mouse model: evidence for specific inhibition of P2Y12 receptors by prasugrel. | 2007 Oct 1 |
|
| The reversible P2Y antagonist cangrelor influences the ability of the active metabolites of clopidogrel and prasugrel to produce irreversible inhibition of platelet function. | 2008 Jul |
|
| Prasugrel: new drug. After angioplasty and stenting: continue to use aspirin + clopidogrel. | 2009 Oct |
|
| Ticagrelor and prasugrel: two novel, most-promising antiplatelet agents. | 2010 Nov |
|
| Importance of potent P2Y(12) receptor blockade in acute myocardial infarction: focus on prasugrel. | 2012 Aug |
|
| Nonclinical assessment of carcinogenic risk and tumor growth enhancement potential of prasugrel, a platelet-inhibiting therapeutic agent. | 2012 Jul-Aug |
|
| Toxicity of thienopyridines on human neutrophil granulocytes and lymphocytes. | 2013 Jun 7 |
Sample Use Guides
Initiate treatment with a single 60 mg oral loading dose.
• Continue at 10 mg once daily with or without food. Consider 5 mg once daily for patients < 60 kg
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 17:31:31 UTC 2023
by
admin
on
Thu Jul 06 17:31:31 UTC 2023
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| Record UNII |
VC4YSF7KNU
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| Record Status |
Validated (UNII)
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| Record Version |
|
-
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9870150
Created by
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389574-20-3
Created by
admin on Thu Jul 06 17:31:31 UTC 2023 , Edited by admin on Thu Jul 06 17:31:31 UTC 2023
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VC4YSF7KNU
Created by
admin on Thu Jul 06 17:31:31 UTC 2023 , Edited by admin on Thu Jul 06 17:31:31 UTC 2023
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PRIMARY |
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|---|---|---|---|---|
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PARENT -> SALT/SOLVATE |
