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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
Structure of PRASUGREL MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CC(=O)OC1=CC2=C(CCN(C2)C(C(=O)C3CC3)C4=CC=CC=C4F)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-

HIDE SMILES / InChI

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

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 ( + / - )

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

2009
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
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
Substance Class Chemical
Created
by admin
on Tue Apr 01 17:24:15 GMT 2025
Edited
by admin
on Tue Apr 01 17:24:15 GMT 2025
Record UNII
VC4YSF7KNU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRASUGREL MALEATE
Common Name English
ETHANONE, 2-(2-(ACETYLOXY)-6,7-DIHYDROTHIENO(3,2-C)PYRIDIN-5(4H)-YL)-1-CYCLOPROPYL-2-(2-FLUOROPHENYL)-, (2Z)-2-BUTENEDIOATE (1:1)
Preferred Name English
Code System Code Type Description
PUBCHEM
9870150
Created by admin on Tue Apr 01 17:24:15 GMT 2025 , Edited by admin on Tue Apr 01 17:24:15 GMT 2025
PRIMARY
CAS
389574-20-3
Created by admin on Tue Apr 01 17:24:15 GMT 2025 , Edited by admin on Tue Apr 01 17:24:15 GMT 2025
PRIMARY
FDA UNII
VC4YSF7KNU
Created by admin on Tue Apr 01 17:24:15 GMT 2025 , Edited by admin on Tue Apr 01 17:24:15 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE