Dipyridamole (CED0002654)

Record Information
Version1.0
Creation Date2016-05-22 04:28:11 UTC
Update Date2026-08-22 04:12:58 UTC
Accession NumberCHEM017570
Identification
Common NameDipyridamole
ClassSmall Molecule
Description
Dipyridamole belongs to the amines, a subclass of organonitrogen compounds within the organic compounds. With an average molecular weight of 504.63 g/mol, Dipyridamole is a heavy molecule. It has the chemical formula C24H40N8O4. In biological contexts, it serves as an antioxidant (PMC7127103). Its recorded protein targets include adenosine deaminase (ADA), cGMP-specific 3',5'-cyclic phosphodiesterase (PDE5A), 3',5'-cyclic-AMP phosphodiesterase 4A (PDE4A), and binder/inhibitor of cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A (PDE10A), along with two other proteins. Within the realm of healthcare, pharmaceuticals, and veterinary products, the compound is used as an antithrombotic agent. It is used as a treatment for thrombosis (PMC12517424) and ischemic stroke (PMC8084398), and it has a therapeutic effect on proteinuria (PMC9368651). Recorded exposure routes include oral and intravenous administration. Additionally, Dipyridamole is found in or released from 15 recorded sources. These include food, food processing, and cookware sources such as food preservation and the preparation of vinegar. It is also found in household cleaning and consumer products, including soap detergents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Finally, it is associated with electrical and electronic equipment, specifically electrodes, electric switches, electrically stimulated smoking devices, antennas, and conductors or conductive bodies characterised by the conductive materials.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
CardoxinChEBI
Cleridium 150ChEBI
CurantylChEBI
DipiridamolChEBI
DipyridamineChEBI
DipyridamolumChEBI
DipyudamineChEBI
DypyridamolChEBI
PersantinChEBI
PersantineKegg
DipyridamolHMDB
Usaf ge-12HMDB
Ashbourne brand OF dipyridamoleHMDB
Berlin chemie brand OF dipyridamoleHMDB
Berlin-chemie brand OF dipyridamoleHMDB
CurantilHMDB
Novo-dipiradolHMDB
Novopharm brand OF dipyridamoleHMDB
Boehringer ingelheim brand OF dipyridamoleHMDB
CléridiumHMDB
DipyramidoleHMDB
AntistenocardinHMDB
Apo-dipyridamoleHMDB
CerebrovaseHMDB
MiosenHMDB
Apotex brand OF dipyridamoleHMDB
Belmac brand OF dipyridamoleHMDB
IPRAD brand OF dipyridamoleHMDB
KurantilHMDB
Novo dipiradolHMDB
Apo dipyridamoleHMDB
Chemical FormulaC24H40N8O4
Average Molecular Mass504.626 g/mol
Monoisotopic Mass504.317 g/mol
CAS Registry Number58-32-2
IUPAC Name2-({6-[bis(2-hydroxyethyl)amino]-4,8-bis(piperidin-1-yl)-[1,3]diazino[5,4-d]pyrimidin-2-yl}(2-hydroxyethyl)amino)ethan-1-ol
Traditional Namedipyridamole
SMILESOCCN(CCO)C1=NC2=C(N=C(N=C2N2CCCCC2)N(CCO)CCO)C(=N1)N1CCCCC1
InChI IdentifierInChI=1S/C24H40N8O4/c33-15-11-31(12-16-34)23-26-20-19(21(27-23)29-7-3-1-4-8-29)25-24(32(13-17-35)14-18-36)28-22(20)30-9-5-2-6-10-30/h33-36H,1-18H2
InChI KeyIZEKFCXSFNUWAM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentDialkylarylamines
Alternative Parents
Substituents
  • Dialkylarylamine
  • Aminopyrimidine
  • Piperidine
  • Pyrimidine
  • Imidolactam
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Alkanolamine
  • Azacycle
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.92 g/LALOGPS
logP1.52ALOGPS
logP1.81ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)14.97ChemAxon
pKa (Strongest Basic)6.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area145.44 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity142.78 m³·mol⁻¹ChemAxon
Polarizability56.94 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-1013900000-667f6d46e6523b3a3d7aNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-01c1-4100079000-4c029f3c81b99fb85ae2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udl-0291000000-caeb14eb3ea863e020a0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udl-0291000000-2fc7956fe6ea13c73317Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udl-0291000000-2fc7956fe6ea13c73317Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0001190000-346cf73a19cbefa2dc11Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0013490000-839580758bc83767be8fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udl-0291000000-caeb14eb3ea863e020a0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1348890000-aa1e3a113b8c2768cb08Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0000390000-b9d4def1784057f522a6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0btl-0000920000-cc12b54862b2bcd1ab8dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-016u-2003900000-53a9a6cb60455cac32e6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0000590000-50fb399e1dbe0355c7b7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfr-2000930000-1d8f7f2a171ae388588eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-1001900000-f3010c0eafbeb9e97741Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0000090000-26e1f92d5f10dd7af547Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0000490000-5e1743c992f893c13776Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0001910000-61e2845ea7c59a8ca2d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0000090000-c0b4fa18532ec9c61047Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0000900000-360b0b12c29f6afe3e17Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-3203920000-e5a412f24717be48fd32Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6369.0Log mg/kg[3600:11000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
ischemic strokeis_treatment_forNot AvailablePMC8084398
thrombosisis_treatment_forNot AvailablePMC12517424
proteinuriahas_therapeutic_effect_onNot AvailablePMC9368651
migrainehas_therapeutic_effect_onNot AvailablePMC12255647
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
273Antithrombotic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
4 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureExopolyphosphatase PRUNE1Q86TP1HumansPredicted (SEA)0.0778492
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A structureClick to view 3D structurecAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10AQ9Y233HumansPredicted (SEA)12.4559
3',5'-cyclic-AMP phosphodiesterase 4D structureClick to view 3D structure3',5'-cyclic-AMP phosphodiesterase 4DQ08499HumansPredicted (SEA)13.5458
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A structureClick to view 3D structureHigh affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8AO60658HumansPredicted (SEA)4.12601
cGMP-specific 3',5'-cyclic phosphodiesterase structureClick to view 3D structurecGMP-specific 3',5'-cyclic phosphodiesteraseO76074HumansPredicted (SEA)15.2584
Click to view 3D structureDual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11AQ9HCR9HumansPredicted (SEA)8.01847
cGMP-dependent 3',5'-cyclic phosphodiesterase structureClick to view 3D structurecGMP-dependent 3',5'-cyclic phosphodiesteraseO00408HumansPredicted (SEA)15.3363
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abP0DTD1SARS-CoV-2Predicted (SEA)79.7954
Broad substrate specificity ATP-binding cassette transporter ABCG2 structureClick to view 3D structureBroad substrate specificity ATP-binding cassette transporter ABCG2Q9UNQ0HumansPredicted (SEA)102.45
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)32.9302
Equilibrative nucleoside transporter 1 structureClick to view 3D structureEquilibrative nucleoside transporter 1Q99808HumansPredicted (SEA)20.3965
Click to view 3D structurePolyunsaturated fatty acid lipoxygenase ALOX15P12530Oryctolagus cuniculusPredicted (SEA)14.1686
ATP-binding cassette sub-family C member 4 structureClick to view 3D structureATP-binding cassette sub-family C member 4O15439HumansPredicted (SEA)2.41333
Solute carrier family 22 member 2 structureClick to view 3D structureSolute carrier family 22 member 2O15244HumansPredicted (SEA)1.86838
Click to view 3D structurePhosphodiesterase 4AO77823Sus scrofaPredicted (SEA)26.858
Lysosomal acid lipase/cholesteryl ester hydrolase structureClick to view 3D structureLysosomal acid lipase/cholesteryl ester hydrolaseP38571HumansPredicted (SEA)4.04816
Click to view 3D structureMyc proto-oncogene proteinP01109Gallus gallusPredicted (SEA)39.3139
Click to view 3D structureShort transient receptor potential channel 4Q9QUQ5Mus musculusPredicted (SEA)1862.15
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)6702.43
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)2735.39
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A structureClick to view 3D structurecGMP-inhibited 3',5'-cyclic phosphodiesterase 3AQ14432HumansPredicted (SEA)1095.88
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)2797.04
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A structureClick to view 3D structureHigh affinity 3',5'-cyclic-AMP phosphodiesterase 7AQ13946HumansPredicted (SEA)1119.71
Click to view 3D structureSentrin-specific protease 6Q9GZR1HumansPredicted (SEA)1233.52
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A structureClick to view 3D structureHigh affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9AO76083HumansPredicted (SEA)1453.99
Concentrations
Not Available
External Links
DrugBank IDDB00975
HMDB IDHMDB0015110
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDipyridamole
Chemspider ID2997
ChEBI ID4653
PubChem Compound ID3108
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Diener HC, Cunha L, Forbes C, Sivenius J, Smets P, Lowenthal A: European Stroke Prevention Study. 2. Dipyridamole and acetylsalicylic acid in the secondary prevention of stroke. J Neurol Sci. 1996 Nov;143(1-2):1-13.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11098344
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11709364