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Details

Stereochemistry RACEMIC
Molecular Formula C20H20FNO3S
Molecular Weight 373.4429
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRASUGREL

SMILES

CC(=O)Oc1cc2CN(CCc2s1)C(c3ccccc3F)C(=O)C4CC4

InChI

InChIKey=DTGLZDAWLRGWQN-UHFFFAOYSA-N
InChI=1S/C20H20FNO3S/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/h2-5,10,13,19H,6-9,11H2,1H3

HIDE SMILES / InChI

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
EFFIENT

Approved Use

Acute 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 Date

1.24709765E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
153.3 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
178.8 ng × h/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
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
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

Doses

DosePopulationAdverse 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
Dose: 75 mg
Route: oral
Route: single
Dose: 75 mg
Sources:
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...
Other AEs:
Dizziness (1 patient)
Sources:
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

AEs

AESignificanceDosePopulation
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
Dose: 75 mg
Route: oral
Route: single
Dose: 75 mg
Sources:
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

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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

Drug as victim

TargetModalityActivityMetaboliteClinical 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

Tox targets

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day.
2012 Nov 12
Toxicity of thienopyridines on human neutrophil granulocytes and lymphocytes.
2013 Jun 7
Patents

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
Prasugrel used at aconcentration of 10 uM markedly inhibited P-selectin expression on human blood platelets induced by 10 uM ADP
Name Type Language
PRASUGREL
DASH   EMA EPAR   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
NSC-759625
Code English
PRASUGREL [INN]
Common Name English
PRASUGREL [WHO-DD]
Common Name English
2-(2-(ACETYLOXY)-6,7-DIHYDROTHIENO(3,2-C)PYRIDIN-5(4H)-YL)-1-CYCLOPROPYL-2-(2-FLUOROPHENYL)ETHANONE
Systematic Name English
5-((1RS)-2-CYCLOPROPYL-1-(2-FLUOROPHENYL)-2-OXOETHYL)-4,5,6,7-TETRAHYDROTHIENO(3,2-C)PYRIDIN-2-YL ACETATE
Systematic Name English
PRASUGREL [VANDF]
Common Name English
ETHANONE, 2-(2-(ACETYLOXY)-6,7-DIHYDROTHIENO(3,2-C)PYRIDIN-5(4H)-YL)-1-CYCLOPROPYL-2-(2-FLUOROPHENYL)-
Systematic Name English
PRASUGREL [EMA EPAR]
Common Name English
5-(2-CYCLOPROPYL-1-(2-FLUOROPHENYL)-2-OXOETHYL)-4,5,6,7-TETRAHYDROTHIENO(3,2-C)PYRIDIN-2-YL ACETATE
Systematic Name English
PRASUGREL [MI]
Common Name English
LY-640315
Code English
2-ACETOXY-5-(.ALPHA.-CYCLOPROPYLCARBONYL-2-FLUOROBENZYL)-4,5,6,7-TETRAHYDROTHIENO-(3,2-C)PYRIDINE
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000182142
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
NCI_THESAURUS C80483
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
WHO-ATC B01AC22
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
WHO-VATC QB01AC22
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
Code System Code Type Description
LACTMED
Prasugrel
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201772
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY
RXCUI
613391
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB06209
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY
NCI_THESAURUS
C81566
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY
FDA UNII
34K66TBT99
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY
NDF-RT
N0000182143
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY P2Y12 Receptor Antagonists [MoA]
DRUG CENTRAL
4113
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY
IUPHAR
7562
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY
PUBCHEM
6918456
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY
MERCK INDEX
M9103
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
PRASUGREL
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY
HSDB
7995
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY
INN
8503
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY
CAS
150322-43-3
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY
MESH
C408153
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY
EVMPD
SUB30236
Created by admin on Fri Jun 25 22:00:20 UTC 2021 , Edited by admin on Fri Jun 25 22:00:20 UTC 2021
PRIMARY