Identification

Name
Prasugrel
Accession Number
DB06209
Type
Small Molecule
Groups
Approved
Description

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 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
  • Prasugrel
External IDs
CS-747 / LY-640315
Product Ingredients
IngredientUNIICASInChI Key
Prasugrel HydrochlorideG89JQ59I13389574-19-0JALHGCPDPSNJNY-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EffientTablet, film coated10 mg/1OralPhysicians Total Care, Inc.2011-03-15Not applicableUs
EffientTablet, film coated5 mg/1OralEli Lilly & Co. Ltd.2009-07-10Not applicableUs
EffientTablet10 mgOralEli Lilly & Co. Ltd.2010-05-17Not applicableCanada
EffientTablet, film coated10 mg/1OralEli Lilly & Co. Ltd.2009-07-10Not applicableUs00002 5123 30 nlmimage10 e848f457
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 coated10 mgOralDaiichi Sankyo Europe, Gmb H2009-02-23Not applicableEu
EfientTablet, film coated5 mgOralDaiichi Sankyo Europe, Gmb H2009-02-23Not applicableEu
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
PrasugrelTablet, film coated5 mg/1OralMylan Pharmaceuticals2017-08-15Not applicableUs
PrasugrelTablet, film coated5 mg/1OralPanacea Biotec Ltd.2017-10-16Not applicableUs
PrasugrelTablet, film coated10 mg/1OralApotex Corporation2017-10-16Not applicableUs
PrasugrelTablet, film coated5 mg/1OralAscend Laboratories, LLC2017-10-18Not applicableUs
PrasugrelTablet, film coated10 mg/1OralMylan Pharmaceuticals2017-08-15Not applicableUs
PrasugrelTablet, film coated10 mg/1OralPanacea Biotec Ltd.2017-10-16Not applicableUs
PrasugrelTablet, film coated5 mg/1OralAurobindo Pharma2017-10-16Not applicableUs
PrasugrelTablet, film coated10 mg/1OralAscend Laboratories, LLC2017-10-18Not applicableUs
PrasugrelTablet, film coated5 mg/1OralApotex Corporation2017-10-16Not applicableUs
PrasugrelTablet, film coated10 mg/1OralAurobindo Pharma2017-10-16Not applicableUs
International/Other Brands
Effient / Efient (Daiichi Sankyo Co.) / Prasita (Daiichi Sankyo Co.)
Categories
UNII
34K66TBT99
CAS number
150322-43-3
Weight
Average: 373.441
Monoisotopic: 373.114792406
Chemical Formula
C20H20FNO3S
InChI Key
DTGLZDAWLRGWQN-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

Indication

Indicated 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
Pharmacodynamics

Prasugrel 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 action

Prasugrel 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.

TargetActionsOrganism
AP2Y purinoceptor 12
antagonist
Human
Absorption

79% 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 binding

Approximately 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.

Route of elimination

Approximately 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 life

The active metabolite has an elimination half-life of about 7.4 hours (range 2-15 hours).

Clearance

Apparent clearance = 112 - 166 L/hr

Toxicity

LD50 (rat) 1,000 - 2,000 mg/kg; LD50 (rabbit) > 1,000 mg/kg

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not 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
AloxiprinThe risk or severity of adverse effects can be increased when Prasugrel is combined with Aloxiprin.Experimental
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
AnagrelidePrasugrel may increase the anticoagulant activities of Anagrelide.Approved
AncrodPrasugrel may increase the anticoagulant activities of Ancrod.Investigational
AndrographolideAndrographolide may increase the anticoagulant activities of Prasugrel.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, Investigational, 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, Investigational
BeraprostPrasugrel may increase the anticoagulant activities of Beraprost.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, Withdrawn
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
BrinasePrasugrel may increase the anticoagulant activities of Brinase.Experimental
BuflomedilBuflomedil may increase the anticoagulant activities of Prasugrel.Experimental
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
Carbaspirin calciumThe risk or severity of adverse effects can be increased when Prasugrel is combined with Carbaspirin calcium.Experimental, 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, Investigational
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
CilostazolPrasugrel may increase the anticoagulant activities of Cilostazol.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.Approved, 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
CloricromenPrasugrel may increase the anticoagulant activities of Cloricromen.Experimental
ClorindionePrasugrel may increase the anticoagulant activities of Clorindione.Experimental
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
Collagenase clostridium histolyticumThe risk or severity of adverse effects can be increased when Prasugrel is combined with Collagenase clostridium histolyticum.Approved, Investigational
ConivaptanThe serum concentration of Prasugrel can be increased when it is combined with Conivaptan.Approved, Investigational
CrisaboroleThe metabolism of Prasugrel can be decreased when combined with Crisaborole.Approved
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
DarexabanPrasugrel may increase the anticoagulant activities of Darexaban.Investigational
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
DefibrotidePrasugrel may increase the anticoagulant activities of Defibrotide.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
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
DiphenadionePrasugrel may increase the anticoagulant activities of Diphenadione.Experimental
DipyridamoleDipyridamole may increase the anticoagulant activities of Prasugrel.Approved
DitazolePrasugrel may increase the anticoagulant activities of Ditazole.Approved, Withdrawn
DosulepinThe metabolism of Prasugrel can be decreased when combined with Dosulepin.Approved
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 metabolism of Prasugrel can be decreased when 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
EplivanserinPrasugrel may increase the anticoagulant activities of Eplivanserin.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 metabolism of Prasugrel can be decreased when 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 metabolism of Prasugrel can be decreased when combined with Etravirine.Approved
Ferulic acidPrasugrel may increase the anticoagulant activities of Ferulic acid.Experimental
FibrinolysinPrasugrel may increase the anticoagulant activities of Fibrinolysin.Investigational
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
GuacetisalThe risk or severity of adverse effects can be increased when Prasugrel is combined with Guacetisal.Experimental
Hemoglobin crosfumarilThe risk or severity of adverse effects can be increased when Prasugrel is combined with Hemoglobin crosfumaril.Experimental
HeparinPrasugrel may increase the anticoagulant activities of Heparin.Approved, Investigational
HigenaminePrasugrel may increase the anticoagulant activities of Higenamine.Investigational
HydroxytyrosolHydroxytyrosol may increase the anticoagulant activities of Prasugrel.Investigational
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 the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Idelalisib resulting in a loss in efficacy.Approved
IdraparinuxPrasugrel may increase the anticoagulant activities of Idraparinux.Investigational
IfenprodilIfenprodil may increase the anticoagulant activities of Prasugrel.Approved, Investigational, Withdrawn
IfetrobanIfetroban may increase the anticoagulant activities of Prasugrel.Investigational
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
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
LetaxabanPrasugrel may increase the anticoagulant activities of Letaxaban.Investigational
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Prasugrel.Approved, Investigational
LinsidomineLinsidomine may increase the anticoagulant activities of Prasugrel.Experimental
LobeglitazoneThe metabolism of Prasugrel can be decreased when combined with Lobeglitazone.Approved, Investigational
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
ManidipineThe metabolism of Prasugrel can be decreased when combined with Manidipine.Approved, Investigational
MelagatranPrasugrel may increase the anticoagulant activities of Melagatran.Experimental
MesalazineThe risk or severity of adverse effects can be increased when Prasugrel is combined with Mesalazine.Approved
Methyl salicylateThe risk or severity of adverse effects can be increased when Prasugrel is combined with Methyl salicylate.Approved, Vet Approved
MidostaurinThe metabolism of Prasugrel can be decreased when combined with Midostaurin.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 metabolism of Prasugrel can be decreased when combined with Modafinil.Approved, Investigational
NadroparinPrasugrel may increase the anticoagulant activities of Nadroparin.Approved
NafamostatPrasugrel may increase the anticoagulant activities of Nafamostat.Approved, Investigational
NaftopidilNaftopidil may increase the anticoagulant activities of Prasugrel.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, Investigational, 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, Nutraceutical
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
OzagrelPrasugrel may increase the anticoagulant activities of Ozagrel.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, Investigational
ParoxetineThe metabolism of Prasugrel can be decreased when combined with Paroxetine.Approved, Investigational
Pentaerythritol TetranitratePrasugrel may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
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, Investigational
PhenobarbitalThe metabolism of Prasugrel can be increased when combined with Phenobarbital.Approved
PhenprocoumonPrasugrel may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhenytoinThe metabolism of Prasugrel can be increased when combined with Phenytoin.Approved, Vet Approved
PicotamidePrasugrel may increase the anticoagulant activities of Picotamide.Experimental
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.Approved, Experimental, Investigational
ReteplasePrasugrel may increase the anticoagulant activities of Reteplase.Approved
ReviparinPrasugrel may increase the anticoagulant activities of Reviparin.Approved, Investigational
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
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
SarpogrelatePrasugrel may increase the anticoagulant activities of Sarpogrelate.Investigational
SaruplasePrasugrel may increase the anticoagulant activities of Saruplase.Experimental
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.Investigational, 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, Investigational
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, Withdrawn
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
TioclomarolPrasugrel may increase the anticoagulant activities of Tioclomarol.Experimental
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
TopiroxostatThe metabolism of Prasugrel can be decreased when combined with Topiroxostat.Approved, Investigational
TositumomabThe risk or severity of adverse effects can be increased when Prasugrel is combined with Tositumomab.Approved, Investigational
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, Investigational
TrimethoprimThe metabolism of Prasugrel can be decreased when combined with Trimethoprim.Approved, Vet Approved
Trolamine salicylateThe risk or severity of adverse effects can be increased when Prasugrel is combined with Trolamine salicylate.Approved
TroxerutinPrasugrel may increase the anticoagulant activities of Troxerutin.Investigational
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
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
ZucapsaicinThe metabolism of Prasugrel can be decreased when combined with Zucapsaicin.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
Human Metabolome Database
HMDB15625
KEGG Drug
D05597
PubChem Compound
6918456
PubChem Substance
99443238
ChemSpider
5293653
ChEBI
87723
ChEMBL
CHEMBL1201772
PharmGKB
PA154410481
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Prasugrel
ATC Codes
B01AC22 — Prasugrel
AHFS Codes
  • 20:12.18 — Platelet Aggregation Inhibitors
FDA label
Download (1000 KB)
MSDS
Download (134 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceHealthy Volunteers2
1CompletedBasic ScienceSickle Cell Disorders1
1CompletedTreatmentAdverse Effect of Antithrombotic Drugs1
1CompletedTreatmentCoronary Artery Disease2
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentSickle Cell Disorders1
1TerminatedPreventionHuman Immunodeficiency Virus (HIV)1
1TerminatedTreatmentAcute Coronary Syndromes (ACS)1
1Unknown StatusNot AvailableHealthy Volunteers1
2CompletedNot AvailableCoronary Artery Disease1
2CompletedBasic ScienceCoronary Artery Disease1
2CompletedTreatmentAcute Coronary Syndromes (ACS)2
2CompletedTreatmentAcute Coronary Syndromes (ACS) / Coronary Arteriosclerosis1
2CompletedTreatmentCardiovascular Disease (CVD) / Heart Diseases1
2CompletedTreatmentCoronary Artery Disease1
2CompletedTreatmentCoronary Artery Disease / Diabetes Mellitus (DM)1
2CompletedTreatmentSickle Cell Disorders2
2RecruitingTreatmentCritical Illness1
2TerminatedTreatmentCoronary Artery Disease1
2WithdrawnDiagnosticCardiovascular Disease (CVD)1
2, 3Active Not RecruitingTreatmentAcute Coronary Syndromes (ACS) / Percutaneous Coronary Intervention1
2, 3CompletedTreatmentST Elevation Myocardial Infarction (STEMI)1
3Active Not RecruitingTreatmentCoronary Artery Bypass Graft1
3CompletedPreventionAcute Coronary Syndromes (ACS)1
3CompletedTreatmentAcute Coronary Syndromes (ACS)5
3CompletedTreatmentAcute Coronary Syndromes (ACS) / Coronary Arteriosclerosis1
3CompletedTreatmentAcute Coronary Syndromes (ACS) / Coronary Artery Disease2
3CompletedTreatmentAcute Coronary Syndromes (ACS) / ST Elevation Myocardial Infarction (STEMI)1
3CompletedTreatmentAcute Coronary Syndromes (ACS) / Unstable Angina (UA)1
3CompletedTreatmentChronic Renal Failure (CRF) / Hemodialysis-dependent patients1
3CompletedTreatmentCoronary Artery Disease3
3CompletedTreatmentCoronary Stent Implantation / Platelet Inhibition1
3CompletedTreatmentMyocardial Infarction (MI)1
3CompletedTreatmentMyocardial Infarction (MI) / Myocardial Infarction (STEMI) <= 12 Hours / ST Elevation Myocardial Infarction (STEMI)1
3CompletedTreatmentNonvalvular Atrial Fibrillation / Percutaneous Coronary Intervention1
3CompletedTreatmentST Segment Elevation Myocardial Infarction (STEMI)1
3RecruitingPreventionAcute Coronary Syndromes (ACS)1
3RecruitingTreatmentAcute Coronary Syndromes (ACS)1
3RecruitingTreatmentNonvalvular Atrial Fibrillation1
3TerminatedTreatmentST Segment Elevation Myocardial Infarction (STEMI)1
3TerminatedTreatmentSickle Cell Disorders1
3Unknown StatusTreatmentCoronary Artery Disease2
4Active Not RecruitingNot AvailableAcute Coronary Syndromes (ACS)1
4Active Not RecruitingTreatmentCoronary Artery Disease1
4CompletedNot AvailableCoronary Artery Disease1
4CompletedBasic ScienceCoronary Artery Disease1
4CompletedDiagnosticCoronary Artery Disease1
4CompletedSupportive CareAcute Coronary Syndromes (ACS) / Platelet Function1
4CompletedTreatmentAcute Coronary Syndromes (ACS)4
4CompletedTreatmentAcute Coronary Syndromes (ACS) / Coronary Artery Disease2
4CompletedTreatmentAcute Coronary Syndromes (ACS) / Coronary Artery Disease / Percutaneous Coronary Intervention1
4CompletedTreatmentAcute Coronary Syndromes (ACS) / Type 2 Diabetes Mellitus1
4CompletedTreatmentAngioplasty, Balloon, Coronary / Myocardial Infarction (MI) / Platelet Aggregation Inhibitors1
4CompletedTreatmentCardiovascular Disease (CVD)1
4CompletedTreatmentChronic Asthma1
4CompletedTreatmentCoronary Artery Disease5
4CompletedTreatmentCoronary Artery Disease / Endothelial Function1
4CompletedTreatmentHealthy Volunteers / Sepsis1
4CompletedTreatmentHeart Failure With Reduced Ejection Fraction (HFrEF)1
4CompletedTreatmentMyocardial Infarction (MI)1
4CompletedTreatmentPlatelet Reactivity2
4CompletedTreatmentST Segment Elevation Myocardial Infarction (STEMI)1
4Not Yet RecruitingBasic ScienceDiabetes1
4Not Yet RecruitingBasic ScienceDiabetes Mellitus (DM)1
4Not Yet RecruitingTreatmentCardiovascular Disease (CVD)1
4Not Yet RecruitingTreatmentCoronary Artery Disease / ST Elevation Myocardial Infarction (STEMI)1
4RecruitingTreatmentACS - Acute Coronary Syndrome / Cardiopulmonary Arrest With Successful Resuscitation / Hypothermia, Induced1
4RecruitingTreatmentAcute Coronary Syndromes (ACS)2
4RecruitingTreatmentAcute Coronary Syndromes (ACS) / Cardiovascular Disease (CVD) / Coronary Arteriosclerosis / Myocardial Ischemia1
4RecruitingTreatmentAngina Pectoris1
4RecruitingTreatmentCoronary Artery Disease1
4RecruitingTreatmentHeart Attacks1
4RecruitingTreatmentMyocardial Infarction (MI)2
4TerminatedTreatmentAcute Coronary Syndromes (ACS) / Cardiovascular Disease (CVD)2
4TerminatedTreatmentCoronary Artery Disease / Thrombosis1
4Unknown StatusTreatmentAcute Coronary Syndromes (ACS)1
4Unknown StatusTreatmentAcute Coronary Syndromes (ACS) / Haemorrhage / Platelet Thrombus1
4Unknown StatusTreatmentAntiplatelet Agents; Endothelial Function; Pleotropic Effects1
4Unknown StatusTreatmentCoronary Artery Disease1
4Unknown StatusTreatmentCoronary Heart Disease (CHD)1
4Unknown StatusTreatmentMyocardial Infarction (MI)1
4Unknown StatusTreatmentPrimary Percutaneous Coronary Intervention / ST Elevation Myocardial Infarction (STEMI)1
Not AvailableActive Not RecruitingSupportive CareAspirin Exacerbated Asthma / Asthma, Aspirin-Induced1
Not AvailableActive Not RecruitingTreatmentAcute Coronary Syndromes (ACS)1
Not AvailableCompletedTreatmentAcute Coronary Syndromes (ACS) / Coronary Artery Disease1
Not AvailableCompletedTreatmentAnti Platelet Effects1
Not AvailableCompletedTreatmentCoronary Artery Disease1
Not AvailableCompletedTreatmentCoronary Artery Disease / Diabetes Mellitus (DM)1
Not AvailableCompletedTreatmentStable Angina (SA)1
Not AvailableRecruitingNot AvailablePlatelet Aggregation Onhibitors1
Not AvailableUnknown StatusTreatmentCoronary Artery Disease / PCI- Percutaneous Coronary Intervention / Platelet Aggregation Inhibitors1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral10 mg
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral10 mg
Tablet, film coatedOral5 mg
Tablet, film coatedOral5 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6693115No2001-07-032021-07-03Us
CA2077695No2002-08-202012-09-08Canada
US8404703Yes2003-07-022023-07-02Us
US8569325Yes2003-07-022023-07-02Us
US5288726Yes1997-10-142017-10-14Us

Properties

State
Solid
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 RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-056s-2945000000-7653802e8e3994dc55bc

Taxonomy

Description
This compound belongs to the class of organic compounds known as thienopyridines. These are heterocyclic compounds containing a thiophene ring fused to a pyridine ring. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Thienopyridines
Sub Class
Not Available
Direct Parent
Thienopyridines
Alternative Parents
2,3,5-trisubstituted thiophenes / Aralkylamines / Fluorobenzenes / Pyridines and derivatives / Aryl fluorides / Alpha-amino ketones / Heteroaromatic compounds / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives
show 6 more
Substituents
Thienopyridine / 2,3,5-trisubstituted thiophene / Halobenzene / Fluorobenzene / Aralkylamine / Pyridine / Aryl fluoride / Aryl halide / Benzenoid / Monocyclic benzene moiety
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, acetate ester, cyclopropanes, ketone, monofluorobenzenes, thienopyridine (CHEBI:87723)

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
Uniprot Name
P2Y purinoceptor 12
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 ...
Gene Name
CES2
Uniprot ID
O00748
Uniprot Name
Cocaine esterase
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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 un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da

Drug created on March 19, 2008 10:17 / Updated on November 19, 2017 20:33