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
Headache 257.29 32.73 107 730 80072 2277176
Vomiting 124.70 32.73 63 774 71539 2285709
Nausea 108.43 32.73 67 770 112122 2245126
Cerebrovascular accident 106.22 32.73 39 798 20147 2337101
Transient ischaemic attack 95.90 32.73 27 810 5951 2351297
Subdural haematoma 79.22 32.73 19 818 2227 2355021
Hypotension 72.41 32.73 34 803 32402 2324846
Orthostatic hypotension 69.63 32.73 18 819 2861 2354387
Dizziness 69.08 32.73 40 797 58625 2298623
Gastrointestinal haemorrhage 68.86 32.73 25 812 12410 2344838
Neurological symptom 60.52 32.73 13 824 927 2356321
Embolism 56.19 32.73 13 824 1300 2355948
Fall 55.02 32.73 32 805 47067 2310181
Subarachnoid haemorrhage 55.02 32.73 14 823 2086 2355162
Extradural haematoma 48.68 32.73 9 828 296 2356952
Balance disorder 48.01 32.73 18 819 9729 2347519
Sedation 44.07 32.73 13 824 3349 2353899
Diarrhoea 42.64 32.73 34 803 83530 2273718
Cerebral haemorrhage 41.69 32.73 14 823 5490 2351758
Cognitive disorder 38.05 32.73 13 824 5368 2351880

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
Headache 206.21 40.11 84 782 34292 1711623
Cerebral haemorrhage 170.55 40.11 48 818 6229 1739686
Cerebrovascular accident 146.44 40.11 55 811 17811 1728104
Dizziness 114.79 40.11 56 810 34305 1711610
Vomiting 91.82 40.11 50 816 38265 1707650
Gastrointestinal haemorrhage 88.51 40.11 36 830 14231 1731684
Loss of consciousness 87.06 40.11 36 830 14839 1731076
Nausea 70.91 40.11 47 819 51149 1694766
Epistaxis 69.22 40.11 26 840 8280 1737635
Transient ischaemic attack 58.81 40.11 20 846 4771 1741144
Haematemesis 56.59 40.11 19 847 4358 1741557
Hypotension 55.40 40.11 33 833 29621 1716294
Subdural haematoma 48.63 40.11 16 850 3441 1742474

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
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
CHEBI has role CHEBI:50427 platelet aggregation inhibitor
CHEBI has role CHEBI:35620 vasodilator agent
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
D004176 MESH_DESCRIPTOR_UI
4017884 VUID
N0000146237 NUI
C0012582 UMLSCUI
D00302 KEGG_DRUG
64ALC7F90C UNII
1545 INN_ID
2527 MMSL
3521 RXNORM
387371005 SNOMEDCT_US
4619 MMSL
d00213 MMSL
66859009 SNOMEDCT_US
4017884 VANDF
000691 NDDF
CHEMBL932 ChEMBL_ID
DB00975 DRUGBANK_ID
CHEBI:4653 CHEBI
4807 IUPHAR_LIGAND_ID
3108 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Aspirin and Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 0093-3064 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 18 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 0527-1461 TABLET, FILM COATED 25 mg ORAL ANDA 11 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 0527-1462 TABLET, FILM COATED 50 mg ORAL ANDA 11 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 0527-1463 TABLET, FILM COATED 75 mg ORAL ANDA 11 sections
Aggrenox HUMAN PRESCRIPTION DRUG LABEL 2 0597-0001 CAPSULE, EXTENDED RELEASE 200 mg ORAL NDA 19 sections
Persantine HUMAN PRESCRIPTION DRUG LABEL 1 0597-0017 TABLET, COATED 25 mg ORAL NDA 11 sections
Persantine HUMAN PRESCRIPTION DRUG LABEL 1 0597-0018 TABLET, COATED 50 mg ORAL NDA 11 sections
Persantine HUMAN PRESCRIPTION DRUG LABEL 1 0597-0019 TABLET, COATED 75 mg ORAL NDA 11 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 0615-1573 TABLET, FILM COATED 50 mg ORAL ANDA 11 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 0641-2569 INJECTION 5 mg INTRAVENOUS ANDA 11 sections
Aspirin and Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 16714-964 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 18 sections
Aggrenox HUMAN PRESCRIPTION DRUG LABEL 2 21695-656 CAPSULE 200 mg ORAL NDA 15 sections
Aspirin and Extended-Release Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 42291-116 CAPSULE 200 mg ORAL ANDA 17 sections
Aspirin and Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 43598-339 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 18 sections
Aspirin and Dipyridamole Extended Release HUMAN PRESCRIPTION DRUG LABEL 2 47335-927 CAPSULE 200 mg ORAL ANDA 17 sections
Aspirin and Extended - Release Dipyridamole Capsules, 25 mg / 200 mg HUMAN PRESCRIPTION DRUG LABEL 2 49884-007 CAPSULE 200 mg ORAL ANDA 16 sections
Aspirin and Extended-Release Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 51407-271 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 17 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 17 sections
Aspirin and Extended-Release Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 62175-330 CAPSULE, EXTENDED RELEASE 200 mg ORAL ANDA 16 sections
Aspirin and Extended-Release Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 62559-850 CAPSULE 200 mg ORAL ANDA 18 sections
DIPYRIDAMOLE HUMAN PRESCRIPTION DRUG LABEL 1 64980-133 TABLET, FILM COATED 25 mg ORAL ANDA 11 sections
DIPYRIDAMOLE HUMAN PRESCRIPTION DRUG LABEL 1 64980-134 TABLET, FILM COATED 50 mg ORAL ANDA 11 sections
DIPYRIDAMOLE HUMAN PRESCRIPTION DRUG LABEL 1 64980-135 TABLET, FILM COATED 75 mg ORAL ANDA 11 sections
Aspirin and Extended-Release Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 2 65162-596 CAPSULE 200 mg ORAL ANDA 18 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 65841-662 TABLET, FILM COATED 25 mg ORAL ANDA 10 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 65841-663 TABLET, FILM COATED 50 mg ORAL ANDA 10 sections
Dipyridamole HUMAN PRESCRIPTION DRUG LABEL 1 65841-664 TABLET, FILM COATED 75 mg ORAL ANDA 10 sections