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Identification
NamePrasugrel
Accession NumberDB06209
TypeSmall Molecule
GroupsApproved
DescriptionPrasugrel, 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 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.
Structure
Thumb
Synonyms
Effient
Prasugrel
External Identifiers
  • CS-747
  • LY-640315
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EffientTablet, film coated10 mg/1OralPhysicians Total Care, Inc.2011-03-15Not applicableUs
EffientTablet, film coated5 mg/1OralEli Lilly and Company2009-07-10Not applicableUs
EffientTablet10 mgOralEli Lilly Canada Inc2010-05-17Not applicableCanada
EffientTablet, film coated10 mg/1OralEli Lilly and Company2009-07-10Not applicableUs
EffientTablet, film coated10 mg/1OralCardinal Health2012-03-01Not applicableUs
EfientTablet, film coated5 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated10 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated10 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated5 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated5 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated10 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated10 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated5 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated5 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated5 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated10 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated5 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated10 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated5 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated10 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
EfientTablet, film coated10 mgOralDaiichi Sankyo Europe Gmb H2009-02-23Not applicableEu
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EfientDaiichi Sankyo Co.
PrasitaDaiichi Sankyo Co.
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Prasugrel Hydrochloride
Thumb
  • InChI Key: JALHGCPDPSNJNY-UHFFFAOYNA-N
  • Monoisotopic Mass: 409.091470145
  • Average Mass: 409.902
DBSALT000145
Categories
UNII34K66TBT99
CAS number150322-43-3
WeightAverage: 373.441
Monoisotopic: 373.114792406
Chemical FormulaC20H20FNO3S
InChI KeyDTGLZDAWLRGWQN-UHFFFAOYSA-N
InChI
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
IUPAC Name
5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4H,5H,6H,7H-thieno[3,2-c]pyridin-2-yl acetate
SMILES
CC(=O)OC1=CC2=C(CCN(C2)C(C(=O)C2CC2)C2=CC=CC=C2F)S1
Pharmacology
IndicationIndicated in combination with acetylsalicylic acid (ASA) to prevent atherothrombotic events in patients with acute coronary syndrome (ACS) who are to be managed with percutaneous coronary intervention (PCI). May be used in patients with unstable angina (UA), non-ST elevation myocardial infarction (NSTEMI), ST-elevation myocardial infarction (STEMI) who are to be managed with PCI. Prasugrel is not recommended in patients 75 years of age or greater, those that weigh<60kg, and patients with a history of stroke or transient ischemic attack due to increased risk of fatal and intracranial bleeding.
Structured Indications
PharmacodynamicsPrasugrel is a member of the thienopyridine class of ADP receptor inhibitors, like ticlopidine (trade name Ticlid) and clopidogrel (trade name Plavix). These agents reduce the aggregation ("clumping") of platelets by irreversibly binding to P2Y12 receptors. Compared to clopidogrel, prasugrel inhibits adenosine diphosphate–induced platelet aggregation more rapidly, more consistently, and to a greater extent than do standard and higher doses of clopidogrel in healthy volunteers and in patients with coronary artery disease, including those undergoing PCI. The increased potency of prasugrel appears to be due to more efficient conversion to its active metabolite. However, it carries a higher risk of bleed compared to clopidogrel, which may be a result of its higher potency. Prasugrel produces inhibition of platelet aggregation to 20 μM or 5 μM ADP, as measured by light transmission aggregometry.
Mechanism of actionPrasugrel is an thienopyridine and a prodrug which inhibits ADP receptors by irreversibly acting on the P2Y12 receptor on platelets. The active metabolite of prasugrel prevents binding of adenosine diphosphate (ADP) to its platelet receptor, impairing the ADP-mediated activation of the glycoprotein GPIIb/IIIa complex. Prasugrel is proposed to have a similar mechanism of action to clopidogrel.
TargetKindPharmacological actionActionsOrganismUniProt ID
P2Y purinoceptor 12Proteinyes
antagonist
HumanQ9H244 details
Related Articles
Absorption79% or greater of the dose is absorbed after oral administration. Absorption and metabolism occur rapidly and peak plasma concentrations (Cmax) are reached approximately 30 minutes following oral administration. Administration with a high fat, high calorie meal did not affect the AUC of the active metabolite in healthy individuals, but the Cmax was decreased by ~49% and the Tmax was increased to 0.5 to 1.5 hours. Prasugrel may be administered with or without food.
Volume of distribution

44-68L

Protein bindingApproximately 98% of the active metabolite was bound to human serum albumin in a 4% buffered solution. The major inactive metabolites are also highly bound to human plasma proteins.
Metabolism

Prasugrel is not detected in plasma following oral administration. It is rapidly hydrolyzed in the intestine to thiolactone by human carboxylesterase (hCE) 2. This intermediate is further metabolized to its active metabolite, R-138727, in a single step by cytochrome P450 enzymes in the liver (primarily CYP3A4 and CYP2B6 and to a lesser extent by CYP2C9 and CYP2C19). The active metabolite is further metabolized by S-methylation or cysteine conjugation to two inactive metabolites. Unlike clopidogrel, transformation of prasugrel to its active metabolite does not appear to be affected by cytochrome P450 polymorphisms.

SubstrateEnzymesProduct
Prasugrel
R-95913Details
R-95913
R-138727Details
Route of eliminationApproximately 68% of the orally administered dose is excreted in urine and 27% in the feces, as inactive metabolites. The active metabolite is not expected to be removed by dialysis.
Half lifeThe active metabolite has an elimination half-life of about 7.4 hours (range 2-15 hours).
Clearance

Apparent clearance = 112 – 166 L/hr

ToxicityLD50 (rat) 1,000 - 2,000 mg/kg; LD50 (rabbit) > 1,000 mg/kg
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbciximabPrasugrel may increase the anticoagulant activities of Abciximab.Approved
AbirateroneThe metabolism of Prasugrel can be decreased when combined with Abiraterone.Approved
AcenocoumarolPrasugrel may increase the anticoagulant activities of Acenocoumarol.Approved
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Prasugrel is combined with Acetylsalicylic acid.Approved, Vet Approved
AlprostadilAlprostadil may increase the anticoagulant activities of Prasugrel.Approved, Investigational
AlteplasePrasugrel may increase the anticoagulant activities of Alteplase.Approved
ALX-0081Prasugrel may increase the anticoagulant activities of ALX-0081.Investigational
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Prasugrel is combined with Aminosalicylic Acid.Approved
AmiodaroneThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Amiodarone resulting in a loss in efficacy.Approved, Investigational
AnagrelideAnagrelide may increase the anticoagulant activities of Prasugrel.Approved
AncrodPrasugrel may increase the anticoagulant activities of Ancrod.Investigational
AnistreplasePrasugrel may increase the anticoagulant activities of Anistreplase.Approved
Antithrombin III humanPrasugrel may increase the anticoagulant activities of Antithrombin III human.Approved
ApixabanThe risk or severity of adverse effects can be increased when Prasugrel is combined with Apixaban.Approved
AprepitantThe serum concentration of Prasugrel can be increased when it is combined with Aprepitant.Approved, Investigational
AprotininThe therapeutic efficacy of Prasugrel can be decreased when used in combination with Aprotinin.Approved, Withdrawn
ArdeparinPrasugrel may increase the anticoagulant activities of Ardeparin.Approved, Withdrawn
ArgatrobanPrasugrel may increase the anticoagulant activities of Argatroban.Approved, Investigational
ArmodafinilThe metabolism of Prasugrel can be decreased when combined with Armodafinil.Approved, Investigational
AstaxanthinPrasugrel may increase the anticoagulant activities of Astaxanthin.Investigational
AtazanavirThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Atazanavir resulting in a loss in efficacy.Approved, Investigational
AtomoxetineThe metabolism of Prasugrel can be decreased when combined with Atomoxetine.Approved
AzelastineAzelastine may increase the anticoagulant activities of Prasugrel.Approved
BalsalazideThe risk or severity of adverse effects can be increased when Prasugrel is combined with Balsalazide.Approved, Investigational
BatroxobinPrasugrel may increase the anticoagulant activities of Batroxobin.Experimental
BecaplerminPrasugrel may increase the anticoagulant activities of Becaplermin.Approved, Investigational
BemiparinPrasugrel may increase the anticoagulant activities of Bemiparin.Approved
BeraprostBeraprost may increase the anticoagulant activities of Prasugrel.Investigational
BexaroteneThe serum concentration of Prasugrel can be decreased when it is combined with Bexarotene.Approved, Investigational
BivalirudinPrasugrel may increase the anticoagulant activities of Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Boceprevir resulting in a loss in efficacy.Approved
BortezomibThe metabolism of Prasugrel can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Prasugrel can be decreased when it is combined with Bosentan.Approved, Investigational
ButylphthalideButylphthalide may increase the anticoagulant activities of Prasugrel.Investigational
CangrelorCangrelor may decrease the antiplatelet activities of Prasugrel.Approved
CapecitabineThe metabolism of Prasugrel can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Prasugrel can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Prasugrel can be increased when it is combined with Ceritinib.Approved
CertoparinPrasugrel may increase the anticoagulant activities of Certoparin.Approved
ChloramphenicolThe metabolism of Prasugrel can be decreased when combined with Chloramphenicol.Approved, Vet Approved
CholecalciferolThe metabolism of Prasugrel can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CilostazolCilostazol may increase the anticoagulant activities of Prasugrel.Approved
CimetidineThe metabolism of Prasugrel can be decreased when combined with Cimetidine.Approved
CitalopramThe metabolism of Prasugrel can be decreased when combined with Citalopram.Approved
Citric AcidPrasugrel may increase the anticoagulant activities of Citric Acid.Nutraceutical, Vet Approved
ClarithromycinThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Clarithromycin resulting in a loss in efficacy.Approved
ClemastineThe metabolism of Prasugrel can be decreased when combined with Clemastine.Approved
ClopidogrelThe metabolism of Prasugrel can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe metabolism of Prasugrel can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Cobicistat resulting in a loss in efficacy.Approved
CollagenaseThe risk or severity of adverse effects can be increased when Prasugrel is combined with Collagenase.Approved
ConivaptanThe serum concentration of Prasugrel can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Prasugrel can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Prasugrel can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilatePrasugrel may increase the anticoagulant activities of Dabigatran etexilate.Approved
DabrafenibThe serum concentration of Prasugrel can be decreased when it is combined with Dabrafenib.Approved
DalteparinPrasugrel may increase the anticoagulant activities of Dalteparin.Approved
DanaparoidPrasugrel may increase the anticoagulant activities of Danaparoid.Approved, Withdrawn
DarunavirThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Darunavir resulting in a loss in efficacy.Approved
DasatinibDasatinib may increase the anticoagulant activities of Prasugrel.Approved, Investigational
DeferasiroxThe serum concentration of Prasugrel can be decreased when it is combined with Deferasirox.Approved, Investigational
DefibrotideDefibrotide may increase the anticoagulant activities of Prasugrel.Approved, Investigational
DelavirdineThe metabolism of Prasugrel can be decreased when combined with Delavirdine.Approved
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Prasugrel is combined with Deoxycholic Acid.Approved
dersalazineThe risk or severity of adverse effects can be increased when Prasugrel is combined with dersalazine.Investigational
DesipramineThe metabolism of Prasugrel can be decreased when combined with Desipramine.Approved
DesirudinPrasugrel may increase the anticoagulant activities of Desirudin.Approved
DesmoteplasePrasugrel may increase the anticoagulant activities of Desmoteplase.Investigational
DexamethasoneThe serum concentration of Prasugrel can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextranPrasugrel may increase the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Prasugrel may increase the anticoagulant activities of Dextran 40.Approved
Dextran 70Prasugrel may increase the anticoagulant activities of Dextran 70.Approved
Dextran 75Prasugrel may increase the anticoagulant activities of Dextran 75.Approved
DicoumarolPrasugrel may increase the anticoagulant activities of Dicoumarol.Approved
DiflunisalThe risk or severity of adverse effects can be increased when Prasugrel is combined with Diflunisal.Approved
DihydroergotamineThe metabolism of Prasugrel can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Prasugrel can be decreased when combined with Diltiazem.Approved
DipyridamoleDipyridamole may increase the anticoagulant activities of Prasugrel.Approved
DitazolePrasugrel may increase the anticoagulant activities of Ditazole.Approved, Withdrawn
DoxorubicinThe metabolism of Prasugrel can be decreased when combined with Doxorubicin.Approved, Investigational
DoxycyclineThe metabolism of Prasugrel can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Prasugrel can be decreased when combined with Dronedarone.Approved
Drotrecogin alfaPrasugrel may increase the anticoagulant activities of Drotrecogin alfa.Approved, Investigational, Withdrawn
Edetic AcidPrasugrel may increase the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanPrasugrel may increase the anticoagulant activities of Edoxaban.Approved
EfavirenzThe serum concentration of Prasugrel can be decreased when it is combined with Efavirenz.Approved, Investigational
EnoxaparinPrasugrel may increase the anticoagulant activities of Enoxaparin.Approved
EnzalutamideThe serum concentration of Prasugrel can be decreased when it is combined with Enzalutamide.Approved
EpinastineEpinastine may increase the anticoagulant activities of Prasugrel.Approved, Investigational
eplivanserinePrasugrel may increase the anticoagulant activities of eplivanserine.Investigational
EpoprostenolEpoprostenol may increase the antiplatelet activities of Prasugrel.Approved
EptifibatideEptifibatide may increase the anticoagulant activities of Prasugrel.Approved, Investigational
ErythromycinThe metabolism of Prasugrel can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Prasugrel can be decreased when it is combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Prasugrel can be decreased when combined with Esomeprazole.Approved, Investigational
Ethyl biscoumacetatePrasugrel may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtravirineThe serum concentration of Prasugrel can be decreased when it is combined with Etravirine.Approved
FibrinolysinPrasugrel may increase the anticoagulant activities of Fibrinolysin.Approved
FloxuridineThe metabolism of Prasugrel can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Prasugrel can be decreased when combined with Fluconazole.Approved
FluindionePrasugrel may increase the anticoagulant activities of Fluindione.Investigational
FluorouracilThe metabolism of Prasugrel can be decreased when combined with Fluorouracil.Approved
FluoxetineThe metabolism of Prasugrel can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvastatinThe metabolism of Prasugrel can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Prasugrel can be decreased when combined with Fluvoxamine.Approved, Investigational
FondaparinuxPrasugrel may increase the anticoagulant activities of Fondaparinux.Investigational
Fondaparinux sodiumPrasugrel may increase the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
FosamprenavirThe metabolism of Prasugrel can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Prasugrel can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Prasugrel can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Prasugrel can be increased when it is combined with Fusidic Acid.Approved
GabexatePrasugrel may increase the anticoagulant activities of Gabexate.Investigational
GemfibrozilThe metabolism of Prasugrel can be decreased when combined with Gemfibrozil.Approved
GlucosamineGlucosamine may increase the antiplatelet activities of Prasugrel.Approved
HeparinPrasugrel may increase the anticoagulant activities of Heparin.Approved, Investigational
HigenaminePrasugrel may increase the anticoagulant activities of Higenamine.Investigational
HirulogPrasugrel may increase the anticoagulant activities of Hirulog.Experimental
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Prasugrel is combined with Ibritumomab tiuxetan.Approved
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Prasugrel.Approved
IbudilastIbudilast may increase the anticoagulant activities of Prasugrel.Approved, Investigational
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Prasugrel.Approved, Nutraceutical
IdelalisibThe serum concentration of Prasugrel can be increased when it is combined with Idelalisib.Approved
idraparinuxPrasugrel may increase the anticoagulant activities of idraparinux.Investigational
IfenprodilIfenprodil may increase the anticoagulant activities of Prasugrel.Approved, Withdrawn
IloprostIloprost may increase the antiplatelet activities of Prasugrel.Approved, Investigational
ImatinibThe metabolism of Prasugrel can be decreased when combined with Imatinib.Approved
IndinavirThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Indinavir resulting in a loss in efficacy.Approved
IndobufenPrasugrel may increase the anticoagulant activities of Indobufen.Investigational
IrbesartanThe metabolism of Prasugrel can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Prasugrel can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Prasugrel can be decreased when combined with Isoniazid.Approved
IsradipineThe metabolism of Prasugrel can be decreased when combined with Isradipine.Approved
ItraconazoleThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Itraconazole resulting in a loss in efficacy.Approved, Investigational
IvacaftorThe serum concentration of Prasugrel can be increased when it is combined with Ivacaftor.Approved
Kct 0809Prasugrel may increase the anticoagulant activities of Kct 0809.Investigational
KetanserinKetanserin may increase the anticoagulant activities of Prasugrel.Investigational
KetoconazoleThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Ketoconazole resulting in a loss in efficacy.Approved, Investigational
LeflunomideThe metabolism of Prasugrel can be decreased when combined with Leflunomide.Approved, Investigational
LepirudinPrasugrel may increase the anticoagulant activities of Lepirudin.Approved
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Prasugrel.Approved
LopinavirThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Lopinavir resulting in a loss in efficacy.Approved
LosartanThe metabolism of Prasugrel can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Prasugrel can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Prasugrel can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Prasugrel can be decreased when it is combined with Lumacaftor.Approved
MesalazineThe risk or severity of adverse effects can be increased when Prasugrel is combined with Mesalazine.Approved
MifepristoneThe serum concentration of Prasugrel can be increased when it is combined with Mifepristone.Approved, Investigational
MilrinoneMilrinone may increase the anticoagulant activities of Prasugrel.Approved
MitotaneThe serum concentration of Prasugrel can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Prasugrel can be decreased when combined with Moclobemide.Approved
ModafinilThe serum concentration of Prasugrel can be decreased when it is combined with Modafinil.Approved, Investigational
NadroparinPrasugrel may increase the anticoagulant activities of Nadroparin.Approved
NafamostatPrasugrel may increase the anticoagulant activities of Nafamostat.Investigational
NafcillinThe serum concentration of Prasugrel can be decreased when it is combined with Nafcillin.Approved
NaftopidilNaftopidil may increase the anticoagulant activities of Prasugrel.Investigational
NCX 4016The risk or severity of adverse effects can be increased when Prasugrel is combined with NCX 4016.Investigational
NefazodoneThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Nefazodone resulting in a loss in efficacy.Approved, Withdrawn
NelfinavirThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Nelfinavir resulting in a loss in efficacy.Approved
NetupitantThe serum concentration of Prasugrel can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Prasugrel can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Prasugrel can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of Prasugrel can be decreased when combined with Nilotinib.Approved, Investigational
NimesulideNimesulide may increase the anticoagulant activities of Prasugrel.Approved, Withdrawn
NitroaspirinThe risk or severity of adverse effects can be increased when Prasugrel is combined with Nitroaspirin.Investigational
ObinutuzumabThe risk or severity of adverse effects can be increased when Prasugrel is combined with Obinutuzumab.Approved
OlaparibThe metabolism of Prasugrel can be decreased when combined with Olaparib.Approved
OlsalazineThe risk or severity of adverse effects can be increased when Prasugrel is combined with Olsalazine.Approved
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Prasugrel.Approved
OmeprazoleThe metabolism of Prasugrel can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Prasugrel can be increased when it is combined with Osimertinib.Approved
OtamixabanPrasugrel may increase the anticoagulant activities of Otamixaban.Investigational
PalbociclibThe serum concentration of Prasugrel can be increased when it is combined with Palbociclib.Approved
PantoprazoleThe metabolism of Prasugrel can be decreased when combined with Pantoprazole.Approved
ParnaparinPrasugrel may increase the anticoagulant activities of Parnaparin.Approved
ParoxetineThe metabolism of Prasugrel can be decreased when combined with Paroxetine.Approved, Investigational
PentobarbitalThe metabolism of Prasugrel can be increased when combined with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Prasugrel.Approved
PentoxifyllinePentoxifylline may increase the antiplatelet activities of Prasugrel.Approved, Investigational
PhenindionePrasugrel may increase the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe metabolism of Prasugrel can be increased when combined with Phenobarbital.Approved
PhenprocoumonPrasugrel may increase the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe metabolism of Prasugrel can be increased when combined with Phenytoin.Approved, Vet Approved
PlasminPrasugrel may increase the anticoagulant activities of Plasmin.Investigational
PosaconazoleThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Posaconazole resulting in a loss in efficacy.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Prasugrel can be increased when combined with Primidone.Approved, Vet Approved
Protein CPrasugrel may increase the anticoagulant activities of Protein C.Approved
Protein S humanPrasugrel may increase the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydePrasugrel may increase the anticoagulant activities of Protocatechualdehyde.Approved
PyrimethamineThe metabolism of Prasugrel can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuazepamThe serum concentration of Prasugrel can be increased when it is combined with Quazepam.Approved, Illicit
QuinineThe metabolism of Prasugrel can be decreased when combined with Quinine.Approved
RamatrobanRamatroban may increase the anticoagulant activities of Prasugrel.Investigational
RanitidineThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Ranitidine resulting in a loss in efficacy.Approved
RanolazineThe metabolism of Prasugrel can be decreased when combined with Ranolazine.Approved, Investigational
ResveratrolResveratrol may increase the anticoagulant activities of Prasugrel.Experimental, Investigational
ReteplasePrasugrel may increase the anticoagulant activities of Reteplase.Approved
ReviparinPrasugrel may increase the anticoagulant activities of Reviparin.Approved
RidogrelRidogrel may increase the anticoagulant activities of Prasugrel.Approved
RifabutinThe metabolism of Prasugrel can be increased when combined with Rifabutin.Approved
RifampicinRifampicin may decrease the antiplatelet activities of Prasugrel.Approved
RifapentineThe metabolism of Prasugrel can be increased when combined with Rifapentine.Approved
RitonavirThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Ritonavir resulting in a loss in efficacy.Approved, Investigational
RivaroxabanPrasugrel may increase the anticoagulant activities of Rivaroxaban.Approved
RosiglitazonePrasugrel may increase the anticoagulant activities of Rosiglitazone.Approved, Investigational
Salicylic acidThe risk or severity of adverse effects can be increased when Prasugrel is combined with Salicylic acid.Approved, Vet Approved
SaquinavirThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Saquinavir resulting in a loss in efficacy.Approved, Investigational
SCH-530348SCH-530348 may increase the anticoagulant activities of Prasugrel.Investigational
SecobarbitalThe metabolism of Prasugrel can be increased when combined with Secobarbital.Approved, Vet Approved
SelexipagPrasugrel may increase the anticoagulant activities of Selexipag.Approved
SertralineThe metabolism of Prasugrel can be decreased when combined with Sertraline.Approved
SevofluraneSevoflurane may increase the anticoagulant activities of Prasugrel.Approved, Vet Approved
SildenafilThe metabolism of Prasugrel can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Prasugrel can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Prasugrel can be increased when it is combined with Simeprevir.Approved
SorafenibThe metabolism of Prasugrel can be decreased when combined with Sorafenib.Approved, Investigational
SRT501SRT501 may increase the anticoagulant activities of Prasugrel.Investigational
St. John's WortThe serum concentration of Prasugrel can be decreased when it is combined with St. John&#39;s Wort.Nutraceutical
StiripentolThe serum concentration of Prasugrel can be increased when it is combined with Stiripentol.Approved
StreptokinasePrasugrel may increase the anticoagulant activities of Streptokinase.Approved
SulfadiazineThe metabolism of Prasugrel can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Prasugrel can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Prasugrel can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulodexidePrasugrel may increase the anticoagulant activities of Sulodexide.Approved, Investigational
TelaprevirThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Telaprevir resulting in a loss in efficacy.Approved
TelithromycinThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Telithromycin resulting in a loss in efficacy.Approved
TenecteplasePrasugrel may increase the anticoagulant activities of Tenecteplase.Approved
TesmilifeneTesmilifene may increase the anticoagulant activities of Prasugrel.Investigational
ThiotepaThe metabolism of Prasugrel can be decreased when combined with Thiotepa.Approved
TicagrelorThe metabolism of Prasugrel can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Prasugrel can be decreased when combined with Ticlopidine.Approved
TinzaparinPrasugrel may increase the anticoagulant activities of Tinzaparin.Approved
TipranavirTipranavir may increase the antiplatelet activities of Prasugrel.Approved, Investigational
TirofibanTirofiban may increase the anticoagulant activities of Prasugrel.Approved
TocilizumabThe serum concentration of Prasugrel can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Prasugrel can be decreased when combined with Tolbutamide.Approved
TopiramateThe metabolism of Prasugrel can be decreased when combined with Topiramate.Approved
TositumomabThe risk or severity of adverse effects can be increased when Prasugrel is combined with Tositumomab.Approved
TranilastTranilast may increase the anticoagulant activities of Prasugrel.Approved, Investigational
TranylcypromineThe metabolism of Prasugrel can be decreased when combined with Tranylcypromine.Approved
TrapidilTrapidil may increase the anticoagulant activities of Prasugrel.Approved
TreprostinilTreprostinil may increase the antiplatelet activities of Prasugrel.Approved, Investigational
TriflusalPrasugrel may increase the anticoagulant activities of Triflusal.Approved
TrimethoprimThe metabolism of Prasugrel can be decreased when combined with Trimethoprim.Approved, Vet Approved
UrokinasePrasugrel may increase the anticoagulant activities of Urokinase.Approved, Investigational, Withdrawn
Valproic AcidThe metabolism of Prasugrel can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Prasugrel can be decreased when combined with Valsartan.Approved, Investigational
VenlafaxineThe metabolism of Prasugrel can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Prasugrel can be decreased when combined with Verapamil.Approved
Vitamin EVitamin E may increase the antiplatelet activities of Prasugrel.Approved, Nutraceutical, Vet Approved
VorapaxarPrasugrel may increase the anticoagulant activities of Vorapaxar.Approved
VoriconazoleThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Voriconazole resulting in a loss in efficacy.Approved, Investigational
WarfarinPrasugrel may increase the anticoagulant activities of Warfarin.Approved
XimelagatranPrasugrel may increase the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
Ym150Prasugrel may increase the anticoagulant activities of Ym150.Investigational
ZafirlukastThe metabolism of Prasugrel can be decreased when combined with Zafirlukast.Approved, Investigational
ZiprasidoneThe metabolism of Prasugrel can be decreased when combined with Ziprasidone.Approved
Food Interactions
  • Despite being a CYP3A4 inducer, grapefruit juice does not affect the pharmacokinetics of prasugrel
References
Synthesis Reference

Teruhiko Inoue, Kazuyoshi Nakamura, Masahiko Hagihara, Hiroyuki Miyata, Yukinori Wada, Naoyuki Yokota, “Process for Producing High-Purity Prasugrel and Acid Addition Salt Thereof.” U.S. Patent US20090203729, issued August 13, 2009.

US20090203729
General References
  1. Dovlatova NL, Jakubowski JA, Sugidachi A, Heptinstall S: The reversible P2Y antagonist cangrelor influences the ability of the active metabolites of clopidogrel and prasugrel to produce irreversible inhibition of platelet function. J Thromb Haemost. 2008 Jul;6(7):1153-9. doi: 10.1111/j.1538-7836.2008.03020.x. Epub 2008 Jul 1. [PubMed:18485086 ]
  2. Tagarakis GI: Ticagrelor and prasugrel: two novel, most-promising antiplatelet agents. Recent Pat Cardiovasc Drug Discov. 2010 Nov;5(3):208-11. [PubMed:20874669 ]
  3. Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [PubMed:23083110 ]
  4. Jeong YH, Tantry US, Gurbel PA: Importance of potent P2Y(12) receptor blockade in acute myocardial infarction: focus on prasugrel. Expert Opin Pharmacother. 2012 Aug;13(12):1771-96. doi: 10.1517/14656566.2012.704909. Epub 2012 Jul 12. [PubMed:22783896 ]
External Links
ATC CodesB01AC22
AHFS Codes
  • 20:12.18
PDB EntriesNot Available
FDA labelDownload (1000 KB)
MSDSDownload (134 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9352
Caco-2 permeable+0.5325
P-glycoprotein substrateSubstrate0.767
P-glycoprotein inhibitor IInhibitor0.6555
P-glycoprotein inhibitor IINon-inhibitor0.7365
Renal organic cation transporterInhibitor0.5312
CYP450 2C9 substrateNon-substrate0.7508
CYP450 2D6 substrateNon-substrate0.7371
CYP450 3A4 substrateSubstrate0.5402
CYP450 1A2 substrateNon-inhibitor0.5288
CYP450 2C9 inhibitorNon-inhibitor0.5706
CYP450 2D6 inhibitorNon-inhibitor0.7051
CYP450 2C19 inhibitorInhibitor0.7083
CYP450 3A4 inhibitorNon-inhibitor0.7432
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8719
Ames testNon AMES toxic0.6616
CarcinogenicityNon-carcinogens0.9521
BiodegradationNot ready biodegradable0.9961
Rat acute toxicity2.4834 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7927
hERG inhibition (predictor II)Non-inhibitor0.6438
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
TabletOral10 mg
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral5 mg/1
Tablet, film coatedOral10 mg
Tablet, film coatedOral5 mg
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2077695 No2002-08-202012-09-08Canada
US5288726 No1997-04-142017-04-14Us
US6693115 No2001-07-032021-07-03Us
US8404703 No2003-01-022023-01-02Us
US8569325 No2003-01-022023-01-02Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP3.536MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.00237 mg/mLALOGPS
logP3.67ALOGPS
logP4.31ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)14.25ChemAxon
pKa (Strongest Basic)5.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.61 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.81 m3·mol-1ChemAxon
Polarizability37.7 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropylamines. These are compounds containing a phenylpropylamine moiety, which consists of a phenyl group substituted at the third carbon by an propan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropylamines
Direct ParentPhenylpropylamines
Alternative Parents
Substituents
  • Phenylpropylamine
  • Thienopyridine
  • 2,3,5-trisubstituted thiophene
  • Aralkylamine
  • Halobenzene
  • Fluorobenzene
  • Pyridine
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • Acetate salt
  • Thiophene
  • Alpha-aminoketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ketone
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Guanyl-nucleotide exchange factor activity
Specific Function:
Receptor for ADP and ATP coupled to G-proteins that inhibit the adenylyl cyclase second messenger system. Not activated by UDP and UTP. Required for normal platelet aggregation and blood coagulation.
Gene Name:
P2RY12
Uniprot ID:
Q9H244
Molecular Weight:
39438.355 Da
References
  1. Dovlatova NL, Jakubowski JA, Sugidachi A, Heptinstall S: The reversible P2Y antagonist cangrelor influences the ability of the active metabolites of clopidogrel and prasugrel to produce irreversible inhibition of platelet function. J Thromb Haemost. 2008 Jul;6(7):1153-9. doi: 10.1111/j.1538-7836.2008.03020.x. Epub 2008 Jul 1. [PubMed:18485086 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Methylumbelliferyl-acetate deacetylase activity
Specific Function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:
CES2
Uniprot ID:
O00748
Molecular Weight:
61806.41 Da
References
  1. Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [PubMed:23083110 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [PubMed:23083110 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [PubMed:23083110 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [PubMed:23083110 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [PubMed:23083110 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
Comments
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Drug created on March 19, 2008 10:17 / Updated on December 04, 2016 02:44