prasugrel Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
platelet aggregation inhibitors 4113 150322-43-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • prasugrel
  • prasugrel hydrochloride
  • effient
  • efient
  • prasugrel HCl
  • CS-747
  • LY640315
A piperazine derivative and PLATELET AGGREGATION INHIBITOR that is used to prevent THROMBOSIS in patients with ACUTE CORONARY SYNDROME; UNSTABLE ANGINA and MYOCARDIAL INFARCTION, as well as in those undergoing PERCUTANEOUS CORONARY INTERVENTIONS.
  • Molecular weight: 373.44
  • Formula: C20H20FNO3S
  • CLOGP: 3.43
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 0
  • TPSA: 46.61
  • ALOGS: -5.20
  • ROTB: 6

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
10 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 1 % Benet LZ, Broccatelli F, Oprea TI

Approvals:

DateAgencyCompanyOrphan
Feb. 24, 2009 EMA DAIICHI SANKYO EUROPE GMBH
July 10, 2009 FDA ELI LILLY AND CO

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Thrombosis in device 196.82 39.38 32 642 621 2356790
Gastrointestinal haemorrhage 146.73 39.38 42 632 12393 2345018
Vascular stent stenosis 115.04 39.38 16 658 98 2357313
Coronary artery restenosis 108.25 39.38 15 659 89 2357322
Vascular pseudoaneurysm 107.70 39.38 17 657 268 2357143
Angina unstable 92.78 39.38 19 655 1347 2356064
Acute myocardial infarction 86.81 39.38 23 651 5032 2352379
Haemorrhage 81.28 39.38 26 648 11013 2346398
Myocardial infarction 74.69 39.38 28 646 18985 2338426
Contusion 65.72 39.38 23 651 12787 2344624
Chest pain 60.81 39.38 27 647 28110 2329301
Retroperitoneal haemorrhage 56.94 39.38 11 663 575 2356836
Angina pectoris 53.70 39.38 15 659 3972 2353439
Device occlusion 47.35 39.38 10 664 819 2356592
Somnambulism 46.64 39.38 10 664 880 2356531
Thrombosis 41.45 39.38 15 659 9129 2348282
Platelet function test abnormal 41.37 39.38 6 668 51 2357360
Haemoglobin decreased 41.00 39.38 18 656 18133 2339278
Cerebral haemorrhage 40.55 39.38 13 661 5491 2351920

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Thrombosis in device 456.98 42.75 83 1310 868 1744520
Vascular stent stenosis 277.87 42.75 44 1349 177 1745211
Acute myocardial infarction 191.41 42.75 63 1330 8524 1736864
Coronary artery restenosis 171.94 42.75 30 1363 239 1745149
Angina pectoris 162.43 42.75 49 1344 4969 1740419
Chest pain 139.88 42.75 63 1330 19851 1725537
Angina unstable 138.25 42.75 36 1357 2122 1743266
Haemorrhage 130.11 42.75 49 1344 9780 1735608
Gastrointestinal haemorrhage 119.02 42.75 51 1342 14216 1731172
Haemorrhage intracranial 109.88 42.75 33 1360 3277 1742111
Epistaxis 87.05 42.75 35 1358 8271 1737117
Vascular stent thrombosis 82.81 42.75 18 1375 481 1744907
Myocardial infarction 79.92 42.75 48 1345 27126 1718262
Cardiac tamponade 75.32 42.75 19 1374 980 1744408
Haematoma 72.03 42.75 25 1368 3920 1741468
Vascular pseudoaneurysm 70.70 42.75 15 1378 356 1745032
Device occlusion 66.86 42.75 17 1376 905 1744483
Cerebral haemorrhage 57.34 42.75 24 1369 6253 1739135
Pericardial haemorrhage 54.36 42.75 13 1380 535 1744853
Upper gastrointestinal haemorrhage 50.86 42.75 18 1375 2981 1742407
Thrombosis 50.01 42.75 23 1370 7498 1737890
Subdural haematoma 44.73 42.75 17 1376 3440 1741948
Non-cardiac chest pain 44.67 42.75 11 1382 512 1744876
Coronary artery thrombosis 43.77 42.75 11 1382 557 1744831

Pharmacologic Action:

SourceCodeDescription
ATC B01AC22 BLOOD AND BLOOD FORMING ORGANS
ANTITHROMBOTIC AGENTS
ANTITHROMBOTIC AGENTS
Platelet aggregation inhibitors excl. heparin
MeSH PA D006401 Hematologic Agents
MeSH PA D010975 Platelet Aggregation Inhibitors
CHEBI has role CHEBI:50433 platelet glycoprotein-IIb/IIIa receptor antagonist
CHEBI has role CHEBI:35554 cardiovascular drug
CHEBI has role CHEBI:50266 prodrug
FDA PE N0000008832 Decreased Platelet Aggregation
FDA EPC N0000182142 P2Y12 Platelet Inhibitor
FDA MoA N0000182143 P2Y12 Receptor Antagonists

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute coronary syndrome indication 394659003
Percutaneous coronary intervention indication 415070008
Myocardial Reinfarction Prevention indication
Intracranial hemorrhage contraindication 1386000
Acute hemorrhage contraindication 8573003
Acute peptic ulcer with hemorrhage contraindication 12274003
Low blood pressure contraindication 45007003
Hepatic failure contraindication 59927004
Blood coagulation disorder contraindication 64779008 DOID:1247
Aortocoronary artery bypass graft contraindication 67166004
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Cerebrovascular accident contraindication 230690007
Transient ischemic attack contraindication 266257000 DOID:224
Surgical procedure contraindication 387713003
Traumatic injury contraindication 417746004
Significant Bleeding contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 5.53 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 10MG BASE EFFIENT ELI LILLY AND CO N022307 July 10, 2009 RX TABLET ORAL Jan. 12, 2020 PEDIATRIC EXCLUSIVITY
EQ 5MG BASE EFFIENT ELI LILLY AND CO N022307 July 10, 2009 RX TABLET ORAL Jan. 12, 2020 PEDIATRIC EXCLUSIVITY

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
P2Y purinoceptor 12 GPCR ANTAGONIST UNKNOWN CHEMBL

External reference:

IDSource
D000068799 MESH_DESCRIPTOR_UI
4029056 VUID
N0000179815 NUI
C1620287 UMLSCUI
D05597 KEGG_DRUG
34K66TBT99 UNII
8503 INN_ID
443312008 SNOMEDCT_US
613391 RXNORM
26287 MMSL
d07409 MMSL
4029056 VANDF
443129001 SNOMEDCT_US
012994 NDDF
389574-19-0 SECONDARY_CAS_RN
DB06209 DRUGBANK_ID
CHEBI:87715 CHEBI
CHEMBL1201772 ChEMBL_ID
CHEMBL1201773 ChEMBL_ID
6918456 PUBCHEM_CID
7562 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Effient HUMAN PRESCRIPTION DRUG LABEL 1 0002-5121 TABLET, FILM COATED 5 mg ORAL NDA 18 sections
Effient HUMAN PRESCRIPTION DRUG LABEL 1 0002-5123 TABLET, FILM COATED 10 mg ORAL NDA 18 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 0378-5185 TABLET, FILM COATED 5 mg ORAL ANDA 18 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 0378-5186 TABLET, FILM COATED 10 mg ORAL ANDA 18 sections
PRASUGREL HUMAN PRESCRIPTION DRUG LABEL 1 0440-0604 TABLET, FILM COATED 5 mg ORAL ANDA 19 sections
PRASUGREL HUMAN PRESCRIPTION DRUG LABEL 1 0440-0605 TABLET, FILM COATED 10 mg ORAL ANDA 19 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 16729-272 TABLET, FILM COATED 5 mg ORAL ANDA 19 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 16729-273 TABLET, FILM COATED 10 mg ORAL ANDA 19 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 43817-239 TABLET, FILM COATED 5 mg ORAL ANDA 19 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 43817-240 TABLET, FILM COATED 10 mg ORAL ANDA 19 sections
prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 48792-7821 TABLET, FILM COATED 10 mg ORAL ANDA 18 sections
prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 48792-7822 TABLET, FILM COATED 5 mg ORAL ANDA 18 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 50090-4118 TABLET, FILM COATED 10 mg ORAL ANDA 18 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 51407-247 TABLET, FILM COATED 5 mg ORAL ANDA 19 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 51407-248 TABLET, FILM COATED 10 mg ORAL ANDA 19 sections
Effient HUMAN PRESCRIPTION DRUG LABEL 1 54868-6238 TABLET, FILM COATED 10 mg ORAL NDA 20 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 60505-4642 TABLET, FILM COATED 5 mg ORAL ANDA 19 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 60505-4643 TABLET, FILM COATED 10 mg ORAL ANDA 19 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 60687-412 TABLET, FILM COATED 10 mg ORAL ANDA 20 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 65162-001 TABLET, FILM COATED 5 mg ORAL ANDA 18 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 65162-002 TABLET, FILM COATED 10 mg ORAL ANDA 18 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 65862-829 TABLET, FILM COATED 5 mg ORAL ANDA 18 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 65862-830 TABLET, FILM COATED 10 mg ORAL ANDA 18 sections
PRASUGREL HUMAN PRESCRIPTION DRUG LABEL 1 67877-604 TABLET, FILM COATED 5 mg ORAL ANDA 18 sections
PRASUGREL HUMAN PRESCRIPTION DRUG LABEL 1 67877-605 TABLET, FILM COATED 10 mg ORAL ANDA 18 sections