Details of the Drug

General Information of Drug (ID: DMXY30O)

Drug Name
Dipyridamole
Synonyms
Agilease; Anginal; Antistenocardin; Apricor; Cardioflux; Cardoxil; Cardoxin; Cerebrovase; Chilcolan; Cleridium; Coribon; Coridil; Coronarine; Corosan; Coroxin; Curantil; Curantyl; Dipiridamol; Dipyramidole; Dipyridamine; Dipyridamol; Dipyridamolum; Dipyridan; Dipyudamine; Dypyridamol; Gulliostin; Justpertin; Kurantil; Miosen; Natyl; Peridamol; Permiltin; Persantin; Persantine; Piroan; Prandiol; Protangix; Stenocardil; Stenocardiol; Stimolcardio; Apotex Brand of Dipyridamole; Ashbourne Brand of Dipyridamole; Belmac Brand of Dipyridamole; Berlin Chemie Brand of Dipyridamole; Boehringer Ingelheim Brand of Dipyridamole; IPRAD Brand of Dipyridamole; Iv Persantine; Novopharm Brand of Dipyridamole; Cleridium 150; D 9766; Prandiol 75; Apo-Dipyridamole; Apo-Dipyridamole Fc; Apo-Dipyridamole Sc; Berlin-Chemie Brand of Dipyridamole; Dipiridamol [INN-Spanish]; Dipyridamolum [INN-Latin]; Novo-Dipiradol; Persantine (TN); RA-8; Usaf Ge-12; Dipyridamole (JP15/USP/INN); Dipyridamole [USAN:INN:BAN:JAN]; Permole, Persantine, Dipyridan, Dipyridamole; 2,6-Bis(diethanolamine)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine; 2,6-Bis(diethanolamino)-4,8-dipiperidinopyrimido(5,4-d)pyrimidine; 2,6-Bis(diethanolamino)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine
Indication
Disease Entry ICD 11 Status REF
Atrial fibrillation BC81.3 Approved [1]
Chronic heart failure BD1Z Approved [1]
Hypertension BA00-BA04 Approved [2]
Malignant essential hypertension BA00 Approved [1]
Therapeutic Class
Vasodilator Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 504.6
Logarithm of the Partition Coefficient (xlogp) 0.7
Rotatable Bond Count (rotbonds) 12
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 12
ADMET Property
Absorption
The absorption of drug is 70% []
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Clearance
The clearance of drug is 2.3-3.5 mL/min/kg []
Elimination
0.1% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 40 minutes [4]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 13.211 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.009% [4]
Vd
The volume of distribution (Vd) of drug is 1-2.5 L/kg []
Water Solubility
The ability of drug to dissolve in water is measured as 0.007 mg/mL [3]
Chemical Identifiers
Formula
C24H40N8O4
IUPAC Name
2-[[2-[bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol
Canonical SMILES
C1CCN(CC1)C2=NC(=NC3=C2N=C(N=C3N4CCCCC4)N(CCO)CCO)N(CCO)CCO
InChI
InChI=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
InChIKey
IZEKFCXSFNUWAM-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3108
ChEBI ID
CHEBI:4653
CAS Number
58-32-2
DrugBank ID
DB00975
TTD ID
D0F9GE
VARIDT ID
DR00613
INTEDE ID
DR2282
ACDINA ID
D00204
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Phosphodiesterase 5A (PDE5A) TTJ0IQB PDE5A_HUMAN Modulator [6]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [7]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [8]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Alpha-1-acid glycoprotein 1 (ORM1) OTZKSBRE A1AG1_HUMAN Protein Interaction/Cellular Processes [9]
ATP-binding cassette sub-family C member 4 (ABCC4) OTO27PAL MRP4_HUMAN Gene/Protein Processing [10]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [11]
Calcipressin-1 (RCAN1) OT1MVXC7 RCAN1_HUMAN Protein Interaction/Cellular Processes [12]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [13]
Caspase-7 (CASP7) OTAPJ040 CASP7_HUMAN Gene/Protein Processing [13]
CD40 ligand (CD40LG) OT75Z6A6 CD40L_HUMAN Protein Interaction/Cellular Processes [14]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [15]
cGMP-specific 3',5'-cyclic phosphodiesterase (PDE5A) OTT8Q1AP PDE5A_HUMAN Gene/Protein Processing [16]
Equilibrative nucleoside transporter 1 (SLC29A1) OTLOOZZS S29A1_HUMAN Gene/Protein Processing [17]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Atrial fibrillation
ICD Disease Classification BC81.3
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Phosphodiesterase 5A (PDE5A) DTT PDE5A 1.60E-01 -0.25 -0.99
P-glycoprotein 1 (ABCB1) DTP P-GP 2.16E-04 -1.07E+00 -2.77E+00
Breast cancer resistance protein (ABCG2) DTP BCRP 3.39E-04 -4.15E+00 -3.65E+00
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Dipyridamole (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Ketoprofen DMRKXPT Moderate Increased risk of bleeding by the combination of Dipyridamole and Ketoprofen. Chronic pain [MG30] [18]
Levomilnacipran DMV26S8 Moderate Increased risk of bleeding by the combination of Dipyridamole and Levomilnacipran. Chronic pain [MG30] [19]
Anisindione DM2C48U Moderate Increased risk of bleeding by the combination of Dipyridamole and Anisindione. Coagulation defect [3B10] [20]
Regorafenib DMHSY1I Major Increased risk of bleeding by the combination of Dipyridamole and Regorafenib. Colorectal cancer [2B91] [21]
Intedanib DMSTA36 Moderate Increased risk of bleeding by the combination of Dipyridamole and Intedanib. Colorectal cancer [2B91] [22]
Ardeparin DMYRX8B Major Increased risk of bleeding by the combination of Dipyridamole and Ardeparin. Coronary thrombosis [BA43] [23]
Danaparoid DM6CLBN Major Increased risk of bleeding by the combination of Dipyridamole and Danaparoid. Deep vein thrombosis [BD71] [23]
Rivaroxaban DMQMBZ1 Major Increased risk of bleeding by the combination of Dipyridamole and Rivaroxaban. Deep vein thrombosis [BD71] [24]
Sertraline DM0FB1J Moderate Increased risk of bleeding by the combination of Dipyridamole and Sertraline. Depression [6A70-6A7Z] [19]
Vilazodone DM4LECQ Moderate Increased risk of bleeding by the combination of Dipyridamole and Vilazodone. Depression [6A70-6A7Z] [19]
Vortioxetine DM6F1PU Moderate Increased risk of bleeding by the combination of Dipyridamole and Vortioxetine. Depression [6A70-6A7Z] [19]
Milnacipran DMBFE74 Moderate Increased risk of bleeding by the combination of Dipyridamole and Milnacipran. Depression [6A70-6A7Z] [19]
Escitalopram DMFK9HG Moderate Increased risk of bleeding by the combination of Dipyridamole and Escitalopram. Depression [6A70-6A7Z] [19]
Desvenlafaxine DMHD4PE Moderate Increased risk of bleeding by the combination of Dipyridamole and Desvenlafaxine. Depression [6A70-6A7Z] [19]
Clomipramine DMINRKW Moderate Increased risk of bleeding by the combination of Dipyridamole and Clomipramine. Depression [6A70-6A7Z] [19]
Heme DMGC287 Moderate Increased risk of bleeding by the combination of Dipyridamole and Heme. Discovery agent [N.A.] [25]
Apigenin DMI3491 Minor Increased risk of bleeding by the combination of Dipyridamole and Apigenin. Discovery agent [N.A.] [26]
Avapritinib DMK2GZX Major Increased risk of bleeding by the combination of Dipyridamole and Avapritinib. Gastrointestinal stromal tumour [2B5B] [21]
Calaspargase pegol DMQZBXI Moderate Increased risk of bleeding by the combination of Dipyridamole and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [27]
Fludarabine DMVRLT7 Moderate Interference of cell/tissue uptake of Dipyridamole by Fludarabine. Malignant haematopoietic neoplasm [2B33] [21]
Acalabrutinib DM7GCVW Major Increased risk of bleeding by the combination of Dipyridamole and Acalabrutinib. Mature B-cell lymphoma [2A85] [28]
Ibrutinib DMHZCPO Major Increased risk of bleeding by the combination of Dipyridamole and Ibrutinib. Mature B-cell lymphoma [2A85] [29]
Ponatinib DMYGJQO Major Increased risk of bleeding by the combination of Dipyridamole and Ponatinib. Mature B-cell lymphoma [2A85] [30]
Panobinostat DM58WKG Major Increased risk of bleeding by the combination of Dipyridamole and Panobinostat. Multiple myeloma [2A83] [31]
Dasatinib DMJV2EK Major Increased risk of bleeding by the combination of Dipyridamole and Dasatinib. Myeloproliferative neoplasm [2A20] [32]
Omacetaxine mepesuccinate DMPU2WX Major Increased risk of bleeding by the combination of Dipyridamole and Omacetaxine mepesuccinate. Myeloproliferative neoplasm [2A20] [33]
Prasugrel DM7MT6E Major Increased risk of bleeding by the combination of Dipyridamole and Prasugrel. Myocardial infarction [BA41-BA43] [21]
Vorapaxar DMA16BR Major Increased risk of bleeding by the combination of Dipyridamole and Vorapaxar. Myocardial infarction [BA41-BA43] [34]
Sibutramine DMFJTDI Moderate Increased risk of bleeding by the combination of Dipyridamole and Sibutramine. Obesity [5B80-5B81] [19]
Dexfenfluramine DMJ7YDS Moderate Increased risk of bleeding by the combination of Dipyridamole and Dexfenfluramine. Obesity [5B80-5B81] [19]
Nepafenac DMYK490 Moderate Increased risk of bleeding by the combination of Dipyridamole and Nepafenac. Osteoarthritis [FA00-FA05] [18]
MK-4827 DMLYGH4 Moderate Increased risk of bleeding by the combination of Dipyridamole and MK-4827. Ovarian cancer [2C73] [21]
Ibuprofen DM8VCBE Moderate Increased risk of bleeding by the combination of Dipyridamole and Ibuprofen. Pain [MG30-MG3Z] [18]
Epoprostenol DMUTYR2 Moderate Increased risk of bleeding by the combination of Dipyridamole and Epoprostenol. Pulmonary hypertension [BB01] [35]
Iloprost DMVPZBE Moderate Increased risk of bleeding by the combination of Dipyridamole and Iloprost. Pulmonary hypertension [BB01] [35]
Oxaprozin DM9UB0P Moderate Increased risk of bleeding by the combination of Dipyridamole and Oxaprozin. Rheumatoid arthritis [FA20] [18]
Curcumin DMQPH29 Minor Increased risk of bleeding by the combination of Dipyridamole and Curcumin. Solid tumour/cancer [2A00-2F9Z] [36]
Caplacizumab DMPUKA7 Major Increased risk of bleeding by the combination of Dipyridamole and Caplacizumab. Thrombocytopenia [3B64] [31]
Apixaban DM89JLN Major Increased risk of bleeding by the combination of Dipyridamole and Apixaban. Thrombosis [DB61-GB90] [21]
Cangrelor DM8JRH0 Major Increased risk of bleeding by the combination of Dipyridamole and Cangrelor. Thrombosis [DB61-GB90] [21]
Brilinta DMBR01X Moderate Increased risk of bleeding by the combination of Dipyridamole and Brilinta. Thrombosis [DB61-GB90] [21]
Cabozantinib DMIYDT4 Major Increased risk of bleeding by the combination of Dipyridamole and Cabozantinib. Thyroid cancer [2D10] [37]
Betrixaban DM2C4RF Major Increased risk of bleeding by the combination of Dipyridamole and Betrixaban. Venous thromboembolism [BD72] [38]
⏷ Show the Full List of 43 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Allura red AC dye E00338 33258 Colorant
D&C red no. 30 E00456 3000709 Colorant
FD&C blue no. 2 E00446 2723854 Colorant
methylparaben E00149 7456 Antimicrobial preservative
Propyl 4-hydroxybenzoate E00141 7175 Antimicrobial preservative
Quinoline yellow WS E00309 24671 Colorant
Sodium benzoate E00432 517055 Antimicrobial preservative; lubricant
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Stearic acid E00079 5281 Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sunset yellow FCF E00255 17730 Colorant
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Crospovidone E00626 Not Available Disintegrant
Ferric hydroxide oxide yellow E00539 23320441 Colorant
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Lithol rubin BCA E00607 135423095 Colorant
Magnesium stearate E00208 11177 lubricant
Polysorbate 80 E00665 Not Available Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Polyvinyl alcohol E00666 Not Available Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Saccharose E00091 5988 Binding agent; Coating agent; Cryoprotectant; Diluent; Flavoring agent; Suspending agent; Viscosity-controlling agent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Soybean lecithin E00637 Not Available Other agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
⏷ Show the Full List of 25 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Dipyridamole 25 mg tablet 25 mg Oral Tablet Oral
Dipyridamole 50 mg tablet 50 mg Oral Tablet Oral
Dipyridamole 75 mg tablet 75 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Dipyridamole FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4807).
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
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10 Expression of multidrug transporter MRP4/ABCC4 is a marker of poor prognosis in neuroblastoma and confers resistance to irinotecan in vitro. Mol Cancer Ther. 2005 Apr;4(4):547-53. doi: 10.1158/1535-7163.MCT-04-0161.
11 A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development. Toxicol Sci. 2013 Nov;136(1):216-41.
12 Inhibiting the calcineurin-NFAT (nuclear factor of activated T cells) signaling pathway with a regulator of calcineurin-derived peptide without affecting general calcineurin phosphatase activity. J Biol Chem. 2009 Apr 3;284(14):9394-401. doi: 10.1074/jbc.M805889200. Epub 2009 Feb 3.
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14 The effect of dipyridamole on vascular cell-derived reactive oxygen species. J Pharmacol Exp Ther. 2005 Nov;315(2):494-500. doi: 10.1124/jpet.105.089987. Epub 2005 Jul 26.
15 Identification of environmental chemicals that activate p53 signaling after in vitro metabolic activation. Arch Toxicol. 2022 Jul;96(7):1975-1987. doi: 10.1007/s00204-022-03291-5. Epub 2022 Apr 18.
16 Cyclic GMP mediates apoptosis induced by sulindac derivatives via activation of c-Jun NH2-terminal kinase 1. Clin Cancer Res. 2000 Oct;6(10):4136-41.
17 New role of the human equilibrative nucleoside transporter 1 (hENT1) in epithelial-to-mesenchymal transition in renal tubular cells. J Cell Physiol. 2012 Apr;227(4):1521-8. doi: 10.1002/jcp.22869.
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25 Product Information. Panhematin (hemin). Recordati Rare Diseases Inc, Lebanon, NJ.
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28 Product Information. Calquence (acalabrutinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
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30 Product Information. Iclusig (ponatinib). Ariad Pharmaceuticals Inc, Cambridge, MA.
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32 Product Information. Sprycel (dasatinib). Bristol-Myers Squibb, Princeton, NJ.
33 Product Information. Brukinsa (zanubrutinib). BeiGene USA, Inc, San Mateo, CA.
34 Product Information. Zontivity (vorapaxar). Merck & Company Inc, Whitehouse Station, NJ.
35 Product Information. Flolan (epoprostenol). Glaxo Wellcome, Research Triangle Park, NC.
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37 Product Information. Cometriq (cabozantinib). Exelixis Inc, S San Francisco, CA.
38 Product Information. Bevyxxa (betrixaban). Portola Pharmaceuticals, South San Francisco, CA.