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 134.75 20.72 33 3567 3032 53342434
Myocardial infarction 133.35 20.72 83 3517 99271 53246195
Vascular pseudoaneurysm 101.76 20.72 23 3577 1491 53343975
Vascular stent stenosis 93.27 20.72 18 3582 536 53344930
Acute myocardial infarction 86.48 20.72 43 3557 33192 53312274
Coronary artery restenosis 85.10 20.72 16 3584 413 53345053
Gastrointestinal haemorrhage 75.88 20.72 54 3546 80276 53265190
Angina pectoris 65.48 20.72 34 3566 28691 53316775
Angina unstable 61.65 20.72 22 3578 7446 53338020
Haemorrhage 54.76 20.72 39 3561 57948 53287518
Acute coronary syndrome 41.10 20.72 18 3582 10406 53335060
Chest pain 41.09 20.72 57 3543 190128 53155338
Retroperitoneal haemorrhage 37.63 20.72 12 3588 2882 53342584
Phaeochromocytoma crisis 35.59 20.72 7 3593 230 53345236
Platelet function test abnormal 35.39 20.72 6 3594 84 53345382
Coronary artery occlusion 34.93 20.72 15 3585 8272 53337194
Coronary artery stenosis 31.55 20.72 12 3588 4847 53340619
Coronary artery disease 30.41 20.72 22 3578 33415 53312051
Somnambulism 30.31 20.72 12 3588 5390 53340076
Myopathy 29.57 20.72 14 3586 9678 53335788
Puncture site haemorrhage 28.28 20.72 6 3594 289 53345177
Device occlusion 27.70 20.72 12 3588 6753 53338713
Stent placement 27.47 20.72 10 3590 3577 53341889
Epistaxis 27.06 20.72 28 3572 68682 53276784
Factor V inhibition 24.52 20.72 5 3595 198 53345268
Cardiogenic shock 24.35 20.72 15 3585 17467 53327999
Coronary artery thrombosis 23.97 20.72 7 3593 1252 53344214
Contusion 23.58 20.72 33 3567 110699 53234767
Cerebral haemorrhage 23.39 20.72 18 3582 29978 53315488
Labelled drug-drug interaction medication error 22.26 20.72 12 3588 10887 53334579
Tachycardia paroxysmal 22.20 20.72 5 3595 318 53345148
Coronary arterial stent insertion 22.01 20.72 8 3592 2846 53342620
Coagulation factor V level decreased 21.83 20.72 5 3595 343 53345123
Ocular retrobulbar haemorrhage 20.89 20.72 4 3596 114 53345352

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 376.43 17.85 98 7129 3436 32502863
Vascular stent thrombosis 229.98 17.85 62 7165 2485 32503814
Vascular stent stenosis 201.33 17.85 47 7180 1035 32505264
Acute myocardial infarction 197.37 17.85 133 7094 55016 32451283
Angina pectoris 139.85 17.85 87 7140 31339 32474960
Coronary artery restenosis 136.60 17.85 35 7192 1146 32505153
Myocardial infarction 129.40 17.85 149 7078 125527 32380772
Chest pain 98.26 17.85 129 7098 124008 32382291
Angina unstable 83.71 17.85 45 7182 12310 32493989
Haemorrhage 63.51 17.85 66 7161 49382 32456917
Haemorrhage intracranial 63.16 17.85 41 7186 15846 32490453
Labelled drug-drug interaction medication error 54.22 17.85 34 7193 12379 32493920
Cardiac tamponade 53.63 17.85 25 7202 5050 32501249
Coronary artery stenosis 50.93 17.85 30 7197 9763 32496536
Gastrointestinal haemorrhage 49.04 17.85 77 7150 86805 32419494
Coronary artery occlusion 44.07 17.85 29 7198 11456 32494843
Coronary artery thrombosis 43.38 17.85 17 7210 2244 32504055
Vascular pseudoaneurysm 37.16 17.85 15 7212 2139 32504160
Haematoma 36.07 17.85 36 7191 25648 32480651
Device occlusion 35.63 17.85 21 7206 6837 32499462
Pericardial haemorrhage 35.10 17.85 16 7211 3070 32503229
Cerebral haemorrhage 33.58 17.85 40 7187 34707 32471592
Pulmonary alveolar haemorrhage 32.32 17.85 20 7207 7109 32499190
Epistaxis 32.17 17.85 50 7177 55805 32450494
Upper gastrointestinal haemorrhage 30.88 17.85 32 7195 23817 32482482
Myocardial ischaemia 30.84 17.85 28 7199 17731 32488568
Acute coronary syndrome 30.33 17.85 25 7202 13916 32492383
Obstructive shock 29.02 17.85 5 7222 20 32506279
Intraventricular haemorrhage 28.57 17.85 14 7213 3156 32503143
Coronary artery disease 27.93 17.85 44 7183 49662 32456637
Subdural haematoma 26.24 17.85 27 7200 19926 32486373
Arterial restenosis 22.91 17.85 5 7222 80 32506219
Bladder tamponade 21.71 17.85 7 7220 523 32505776
Platelet function test abnormal 20.99 17.85 5 7222 120 32506179
Peripheral arterial occlusive disease 20.89 17.85 14 7213 5695 32500604
Apnoeic attack 20.85 17.85 6 7221 305 32505994
Melaena 19.90 17.85 31 7196 34634 32471665
Procedural haemorrhage 19.49 17.85 10 7217 2483 32503816
Coombs negative haemolytic anaemia 19.27 17.85 5 7222 172 32506127
Non-cardiac chest pain 19.19 17.85 12 7215 4341 32501958
Vessel puncture site haematoma 18.76 17.85 4 7223 57 32506242
Coronary artery perforation 18.76 17.85 4 7223 57 32506242
Post procedural haemorrhage 18.29 17.85 15 7212 8285 32498014
Cardiac failure 18.11 17.85 53 7174 91620 32414679

Pharmacologic Action:

SourceCodeDescription
ATC B01AC22 BLOOD AND BLOOD FORMING ORGANS
ANTITHROMBOTIC AGENTS
ANTITHROMBOTIC AGENTS
Platelet aggregation inhibitors excl. heparin
FDA PE N0000008832 Decreased Platelet Aggregation
MeSH PA D006401 Hematologic Agents
MeSH PA D010975 Platelet Aggregation Inhibitors
FDA EPC N0000182142 P2Y12 Platelet Inhibitor
FDA MoA N0000182143 P2Y12 Receptor Antagonists
CHEBI has role CHEBI:35554 cardiovascular drugs
CHEBI has role CHEBI:50433 platelet glycoprotein-IIb/IIIa receptor antagonists
CHEBI has role CHEBI:68563 purinergic receptor subtype P2Y12 antagonist
CHEBI has role CHEBI:50266 Prodrugs

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)

None

Bioactivity Summary:

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

External reference:

IDSource
4029056 VUID
N0000179815 NUI
D05597 KEGG_DRUG
389574-19-0 SECONDARY_CAS_RN
4029056 VANDF
4029068 VANDF
C2683417 UMLSCUI
CHEBI:87715 CHEBI
CHEMBL1201772 ChEMBL_ID
DB06209 DRUGBANK_ID
CHEMBL1201773 ChEMBL_ID
D000068799 MESH_DESCRIPTOR_UI
6918456 PUBCHEM_CID
7562 IUPHAR_LIGAND_ID
8503 INN_ID
34K66TBT99 UNII
613391 RXNORM
166281 MMSL
261080 MMSL
26287 MMSL
39620 MMSL
d07409 MMSL
012994 NDDF
012995 NDDF
443129001 SNOMEDCT_US
443312008 SNOMEDCT_US
735166002 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Effient HUMAN PRESCRIPTION DRUG LABEL 1 0002-5121 TABLET, FILM COATED 5 mg ORAL NDA 32 sections
Effient HUMAN PRESCRIPTION DRUG LABEL 1 0002-5123 TABLET, FILM COATED 10 mg ORAL NDA 32 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 0378-5185 TABLET, FILM COATED 5 mg ORAL ANDA 29 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 0378-5186 TABLET, FILM COATED 10 mg ORAL ANDA 29 sections
PRASUGREL HUMAN PRESCRIPTION DRUG LABEL 1 0440-0604 TABLET, FILM COATED 5 mg ORAL ANDA 29 sections
PRASUGREL HUMAN PRESCRIPTION DRUG LABEL 1 0440-0605 TABLET, FILM COATED 10 mg ORAL ANDA 29 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 16729-272 TABLET, FILM COATED 5 mg ORAL ANDA 27 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 16729-273 TABLET, FILM COATED 10 mg ORAL ANDA 27 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 43817-239 TABLET, FILM COATED 5 mg ORAL ANDA 27 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 43817-240 TABLET, FILM COATED 10 mg ORAL ANDA 27 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 50090-4118 TABLET, FILM COATED 10 mg ORAL ANDA 26 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 50090-5169 TABLET, FILM COATED 10 mg ORAL ANDA 27 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 51407-247 TABLET, FILM COATED 5 mg ORAL ANDA 27 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 51407-248 TABLET, FILM COATED 10 mg ORAL ANDA 27 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 51407-444 TABLET, FILM COATED 5 mg ORAL ANDA 29 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 51407-445 TABLET, FILM COATED 10 mg ORAL ANDA 29 sections
Effient HUMAN PRESCRIPTION DRUG LABEL 1 54868-6238 TABLET, FILM COATED 10 mg ORAL NDA 28 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 60505-4642 TABLET, FILM COATED 5 mg ORAL ANDA 27 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 60505-4643 TABLET, FILM COATED 10 mg ORAL ANDA 27 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 65162-001 TABLET, FILM COATED 5 mg ORAL ANDA 26 sections
Prasugrel HUMAN PRESCRIPTION DRUG LABEL 1 65162-002 TABLET, FILM COATED 10 mg ORAL ANDA 26 sections
Effient HUMAN PRESCRIPTION DRUG LABEL 1 65597-601 TABLET, COATED 5 mg ORAL NDA 33 sections
Effient HUMAN PRESCRIPTION DRUG LABEL 1 65597-602 TABLET, COATED 10 mg ORAL NDA 33 sections
Prasugrel Human Prescription Drug Label 1 65862-829 TABLET, FILM COATED 5 mg ORAL ANDA 27 sections
Prasugrel Human Prescription Drug Label 1 65862-830 TABLET, FILM COATED 10 mg ORAL ANDA 27 sections
PRASUGREL HUMAN PRESCRIPTION DRUG LABEL 1 67877-604 TABLET, FILM COATED 5 mg ORAL ANDA 28 sections
PRASUGREL HUMAN PRESCRIPTION DRUG LABEL 1 67877-605 TABLET, FILM COATED 10 mg ORAL ANDA 28 sections