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

Stem definitionDrug idCAS RN
924 58-32-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • dipyridamole
  • cardoxil
  • cardoxin
  • cleridium
  • dipyridamine
  • dipyridamol
  • dipyridan
  • peridamol
  • persantin
  • stenocardil
  • stimolcardio
A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752)
  • Molecular weight: 504.64
  • Formula: C24H40N8O4
  • CLOGP: 1.49
  • LIPINSKI: 2
  • HAC: 12
  • HDO: 4
  • TPSA: 145.44
  • ALOGS: -2.74
  • ROTB: 12

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.40 g O
0.20 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.01 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 13.21 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 50 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.82 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.01 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 13 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 6, 1961 FDA BOEHRINGER INGELHEIM

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
Sedation complication 282.18 14.89 78 9926 3567 46672491
Cerebrovascular accident 226.27 14.89 181 9823 100858 46575200
Orthostatic hypotension 220.68 14.89 107 9897 24551 46651507
Creatinine renal clearance decreased 213.18 14.89 73 9931 6847 46669211
Sedation 209.80 14.89 101 9903 22809 46653249
Cognitive disorder 198.72 14.89 114 9890 36769 46639289
Blood calcium decreased 167.82 14.89 77 9927 15596 46660462
Balance disorder 128.28 14.89 108 9896 64413 46611645
Depressed level of consciousness 127.61 14.89 95 9909 47474 46628584
Transient ischaemic attack 114.97 14.89 79 9925 34824 46641234
Constipation 85.67 14.89 142 9862 173955 46502103
Fall 79.85 14.89 200 9804 328897 46347161
Mobility decreased 69.71 14.89 75 9929 60519 46615539
Hypotension 55.89 14.89 141 9863 232448 46443610
Drug ineffective 49.22 14.89 44 9960 677794 45998264
Cerebral infarction 42.06 14.89 37 9967 23329 46652729
Subdural haematoma 39.44 14.89 28 9976 12969 46663089
Extradural haematoma 28.75 14.89 11 9993 1412 46674646
Embolism 25.48 14.89 17 9987 7121 46668937
Rheumatoid arthritis 25.18 14.89 10 9994 240205 46435853
Neurological symptom 23.92 14.89 14 9990 4665 46671393
Subarachnoid haemorrhage 22.79 14.89 19 9985 11134 46664924
Fatigue 21.09 14.89 64 9940 608633 46067425
Acute myocardial infarction 19.75 14.89 29 9975 31895 46644163
Peripheral swelling 19.35 14.89 5 9999 158066 46517992
Oesophageal ulcer haemorrhage 19.30 14.89 6 9998 413 46675645
Gastrointestinal haemorrhage 18.60 14.89 47 9957 77326 46598732
Nail ridging 18.15 14.89 5 9999 225 46675833
Hyperlipidaemia 17.95 14.89 21 9983 18518 46657540
Cerebral haemorrhage 17.88 14.89 26 9978 28345 46647713
Headache 17.73 14.89 168 9836 478184 46197874
Stress cardiomyopathy 17.46 14.89 14 9990 7770 46668288
Mediastinal haemorrhage 16.97 14.89 3 10001 15 46676043
Off label use 16.96 14.89 35 9969 379806 46296252
Left ventricular end-diastolic pressure increased 16.55 14.89 5 9999 313 46675745
Carotid artery occlusion 16.41 14.89 9 9995 2650 46673408
Toxicity to various agents 15.75 14.89 88 9916 211678 46464380
Joint swelling 15.68 14.89 8 9996 166065 46509993

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
Cerebrovascular accident 266.28 13.49 208 8444 83269 29860557
Transient ischaemic attack 129.07 13.49 84 8568 25116 29918710
Cerebral haemorrhage 67.76 13.49 64 8588 32823 29911003
Headache 45.15 13.49 135 8517 182171 29761655
Splenic injury 32.16 13.49 6 8646 30 29943796
Peritoneal haematoma 28.18 13.49 6 8646 64 29943762
Carotid artery occlusion 24.85 13.49 12 8640 2013 29941813
Drug ineffective 24.41 13.49 38 8614 340349 29603477
Loss of consciousness 23.70 13.49 63 8589 79312 29864514
Cerebral infarction 23.03 13.49 33 8619 26340 29917486
Gastrointestinal haemorrhage 21.72 13.49 63 8589 83383 29860443
Vitreous haemorrhage 21.44 13.49 11 8641 2099 29941727
Labelled drug-drug interaction medication error 20.71 13.49 20 8632 10518 29933308
Aphasia 19.49 13.49 26 8626 19413 29924413
Fine motor delay 18.62 13.49 5 8647 150 29943676
Monocytosis 18.34 13.49 6 8646 360 29943466
Embolic stroke 18.33 13.49 12 8640 3610 29940216
Haemorrhage intracranial 18.06 13.49 22 8630 15010 29928816
Off label use 16.74 13.49 29 8623 249261 29694565
Tubulointerstitial nephritis 16.53 13.49 23 8629 17868 29925958
Ocular myasthenia 16.34 13.49 5 8647 241 29943585
Myalgia 16.34 13.49 54 8598 76613 29867213
Haematemesis 16.22 13.49 28 8624 26175 29917651
Intra-abdominal haemorrhage 15.88 13.49 9 8643 2093 29941733
Hypotension 15.50 13.49 105 8547 200460 29743366
Abdominal sepsis 15.23 13.49 7 8645 1050 29942776
Lacunar infarction 14.87 13.49 10 8642 3145 29940681
Diverticulitis intestinal haemorrhagic 14.35 13.49 5 8647 364 29943462
Lip swelling 14.26 13.49 18 8634 12726 29931100
Fatigue 13.86 13.49 47 8605 320626 29623200
Dizziness 13.86 13.49 100 8552 194809 29749017
Device related thrombosis 13.71 13.49 6 8646 803 29943023
Hemiparesis 13.63 13.49 19 8633 14783 29929043

Pharmacologic Action:

SourceCodeDescription
ATC B01AC07 BLOOD AND BLOOD FORMING ORGANS
ANTITHROMBOTIC AGENTS
ANTITHROMBOTIC AGENTS
Platelet aggregation inhibitors excl. heparin
FDA PE N0000008832 Decreased Platelet Aggregation
FDA EPC N0000175578 Platelet Aggregation Inhibitor
CHEBI has role CHEBI:35620 vasodilator
CHEBI has role CHEBI:50427 platelet aggregation inhibitors
CHEBI has role CHEBI:50445 adenosine deaminase inhibitors
MeSH PA D002317 Cardiovascular Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D006401 Hematologic Agents
MeSH PA D010726 Phosphodiesterase Inhibitors
MeSH PA D010975 Platelet Aggregation Inhibitors
MeSH PA D014665 Vasodilator Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Chronic heart failure indication 48447003
Atrial fibrillation indication 49436004 DOID:0060224
Platelet Aggregation Inhibition indication
Prevention of Cerebral Thrombosis indication
Myocardial Perfusion Imaging Adjunct indication
Cerebral embolism off-label use 75543006 DOID:4372
Transient ischemic attack off-label use 266257000 DOID:224
Thromboembolic disorder off-label use 371039008
Myocardial Reinfarction Prevention off-label use
Alcoholism contraindication 7200002
Poisoning by digitalis glycoside contraindication 12876009
Peptic ulcer contraindication 13200003 DOID:750
Senile cardiac amyloidosis contraindication 16573007
Myocardial infarction contraindication 22298006 DOID:5844
Sick sinus syndrome contraindication 36083008 DOID:13884
Gastrointestinal ulcer contraindication 40845000
Myxedema contraindication 43153006 DOID:11634
Hypokalemia contraindication 43339004
Low blood pressure contraindication 45007003
Sinus bradycardia contraindication 49710005
Myocarditis contraindication 50920009 DOID:820
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Acute nephropathy contraindication 58574008
Hypercalcemia contraindication 66931009 DOID:12678
Ventricular fibrillation contraindication 71908006
Factor II deficiency contraindication 73975000
Reye's syndrome contraindication 74351001 DOID:14525
Wolff-Parkinson-White pattern contraindication 74390002 DOID:384
Gastrointestinal hemorrhage contraindication 74474003
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Cor pulmonale contraindication 83291003 DOID:8515
Constrictive pericarditis contraindication 85598007 DOID:11481
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Hemophilia contraindication 90935002
Anemia due to enzyme deficiency contraindication 111577008
von Willebrand disorder contraindication 128105004 DOID:12531
Hypomagnesemia contraindication 190855004
Atrioventricular block contraindication 233917008 DOID:0050820
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Idiopathic hypertrophic subaortic stenosis contraindication 360465008
Acute coronary syndrome contraindication 394659003
Breastfeeding (mother) contraindication 413712001
Restrictive cardiomyopathy contraindication 415295002 DOID:397
Acute erosive gastritis contraindication 444926003

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.0 Basic
pKa2 8.52 Basic
pKa3 2.75 Basic
pKa4 2.12 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
Phosphodiesterase 1 Enzyme INHIBITOR IC50 4.35 CHEMBL CHEMBL
cGMP-dependent 3',5'-cyclic phosphodiesterase Enzyme INHIBITOR IC50 5.49 CHEMBL CHEMBL
Phosphodiesterase 3 Enzyme INHIBITOR IC50 4.37 CHEMBL CHEMBL
cGMP-specific 3',5'-cyclic phosphodiesterase Enzyme INHIBITOR IC50 6.28 CHEMBL CHEMBL
cAMP-specific 3',5'-cyclic phosphodiesterase 4A Enzyme INHIBITOR IC50 5.80 DRUG MATRIX CHEMBL
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Enzyme INHIBITOR Ki 6 CHEMBL CHEMBL
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A Enzyme INHIBITOR IC50 5.10 CHEMBL CHEMBL
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8B Enzyme INHIBITOR IC50 4.30 IUPHAR CHEMBL
Equilibrative nucleoside transporter 1 Transporter INHIBITOR Ki 8.50 CHEMBL CHEMBL
Phosphodiesterase 6 Enzyme INHIBITOR Ki 6.90 CHEMBL CHEMBL
cAMP-specific 3',5'-cyclic phosphodiesterase 7B Enzyme INHIBITOR IC50 6 CHEMBL CHEMBL
Phosphodiesterase 7 Enzyme INHIBITOR Ki 6.22 CHEMBL CHEMBL
Equilibrative nucleoside transporter 4 Transporter INHIBITOR Ki 5.90 IUPHAR
Sodium/nucleoside cotransporter 1 Transporter INHIBITOR Ki 7.54 DRUG MATRIX
Protein prune homolog Enzyme IC50 6.11 CHEMBL
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A Enzyme Ki 6.40 CHEMBL
Arachidonate 15-lipoxygenase Enzyme IC50 5.16 DRUG MATRIX
Cyclic AMP-specific phosphodiesterase SSPDE4A1A Enzyme IC50 5.28 CHEMBL
Cyclic nucleotide phosphodiesterase PDE3A Enzyme IC50 4.36 CHEMBL
ORF 73 Unclassified AC50 5.05 CHEMBL
Main protease (M-PRO) Enzyme INHIBITOR IC50 6.26 SCIENTIFIC LITERATURE

External reference:

IDSource
4017884 VUID
N0000146237 NUI
D00302 KEGG_DRUG
4017884 VANDF
C0308607 UMLSCUI
CHEBI:4653 CHEBI
CHEMBL932 ChEMBL_ID
DB00975 DRUGBANK_ID
D004176 MESH_DESCRIPTOR_UI
3108 PUBCHEM_CID
4807 IUPHAR_LIGAND_ID
1545 INN_ID
64ALC7F90C UNII
203015 RXNORM
2493 MMSL
2527 MMSL
3353 MMSL
4619 MMSL
d00213 MMSL
000691 NDDF
387371005 SNOMEDCT_US
66859009 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Aspirin and Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 0093-3064 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 27 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 0527-1461 TABLET, FILM COATED 25 mg ORAL ANDA 21 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 0527-1462 TABLET, FILM COATED 50 mg ORAL ANDA 21 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 0527-1463 TABLET, FILM COATED 75 mg ORAL ANDA 21 sections
Aggrenox HUMAN PRESCRIPTION DRUG LABEL 2 0597-0001 CAPSULE, EXTENDED RELEASE 200 mg ORAL NDA 29 sections
Persantine HUMAN PRESCRIPTION DRUG LABEL 1 0597-0017 TABLET, COATED 25 mg ORAL NDA 21 sections
Persantine HUMAN PRESCRIPTION DRUG LABEL 1 0597-0018 TABLET, COATED 50 mg ORAL NDA 21 sections
Persantine HUMAN PRESCRIPTION DRUG LABEL 1 0597-0019 TABLET, COATED 75 mg ORAL NDA 21 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 0641-2569 INJECTION 5 mg INTRAVENOUS ANDA 19 sections
Aspirin and Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 16714-964 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 27 sections
Aggrenox HUMAN PRESCRIPTION DRUG LABEL 2 21695-656 CAPSULE 200 mg ORAL NDA 17 sections
Aspirin and Extended-Release Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 42291-116 CAPSULE 200 mg ORAL ANDA 26 sections
Aspirin and Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 43598-339 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 26 sections
Aspirin and Dipyridamole Extended Release Human Prescription Drug Label 2 47335-927 CAPSULE 200 mg ORAL ANDA 25 sections
Aspirin and Extended - Release Dipyridamole Capsules, 25 mg / 200 mg HUMAN PRESCRIPTION DRUG LABEL 2 49884-007 CAPSULE 200 mg ORAL ANDA 25 sections
Aspirin and Extended-Release Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 51407-271 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 19 sections
DIPYRIDAMOLE HUMAN PRESCRIPTION DRUG LABEL 1 51662-1447 INJECTION 5 mg INTRAVENOUS ANDA 11 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 51808-204 SOLUTION 5 mg INTRAVENOUS Unapproved drug other 7 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 52584-569 INJECTION 5 mg INTRAVENOUS ANDA 11 sections
Aggrenox HUMAN PRESCRIPTION DRUG LABEL 2 54868-5143 CAPSULE 200 mg ORAL NDA 19 sections
Aspirin and Extended-Release Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 62175-330 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 19 sections
Aspirin and Extended-Release Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 62559-850 CAPSULE 200 mg ORAL ANDA 26 sections
DIPYRIDAMOLE HUMAN PRESCRIPTION DRUG LABEL 1 64980-133 TABLET, FILM COATED 25 mg ORAL ANDA 19 sections
DIPYRIDAMOLE HUMAN PRESCRIPTION DRUG LABEL 1 64980-134 TABLET, FILM COATED 50 mg ORAL ANDA 19 sections
DIPYRIDAMOLE HUMAN PRESCRIPTION DRUG LABEL 1 64980-135 TABLET, FILM COATED 75 mg ORAL ANDA 19 sections
Aspirin and Extended-Release Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 65162-596 CAPSULE 200 mg ORAL ANDA 27 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 65841-662 TABLET, FILM COATED 25 mg ORAL ANDA 1 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 65841-663 TABLET, FILM COATED 50 mg ORAL ANDA 1 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 65841-664 TABLET, FILM COATED 75 mg ORAL ANDA 1 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 68151-2996 TABLET 25 mg ORAL NDA authorized generic 17 sections