Synonym
Dipyridamole; Persantin; Dipyridamine; Dipyridamol; NSC-515776; NSC515776; NSC 515776; RA 8; RA8; RA-8;
IUPAC/Chemical Name
2,2',2'',2'''-((4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl)bis(azanetriyl))tetraethanol
InChi Key
IZEKFCXSFNUWAM-UHFFFAOYSA-N
InChi Code
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
SMILES Code
OCCN(CCO)C1=NC(N2CCCCC2)=C(N=C(N(CCO)CCO)N=C3N4CCCCC4)C3=N1
Appearance
Light yellow to yellow crystalline solid.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Dipyridamole is an orally active phosphodiesterase (PDE) inhibitor.
In vitro activity:
A MTT assay is used to evaluate the proliferation of cancer cells. The addition of dipyridamole (0–20 µM) increased the proliferation of U937 cells, parent HCT-8 cells and the CD133+/CD44+ stem-like subpopulation of HCT-8 cells in a dose-dependent manner (Fig. 1A).
Reference: Oncol Lett. 2021 Apr;21(4):251. https://pubmed.ncbi.nlm.nih.gov/33664815/
In vivo activity:
Dipyridamole significantly ameliorated doxorubicin-induced cardiotoxicity in rats, as suggested by the significantly decreased inflammatory mediators TNF-α and IL-6 (Figures 1 and 2). Cardiac tissue level of the oxidative marker MDA significantly decreased (Figure 3) and also significantly increased in TAC (Figure 4) with the dipyridamole group compared to the doxorubicin-only group. Additionally, dipyridamole significantly attenuated doxorubicin-induced apoptosis, reflected by lower cardiac caspase-3 level (Figure 5) and significant elevation in Bcl-2 compared to the doxorubicin-only group (Figure 6).
Reference: J Med Life. 2022 Sep;15(9):1184-1190. https://pubmed.ncbi.nlm.nih.gov/36415530/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
59.45 |
| DMSO |
60.0 |
118.90 |
| DMSO:PBS (pH 7.2) (1:1) |
0.5 |
0.99 |
| Ethanol |
27.5 |
54.50 |
| Water |
0.7 |
1.33 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
504.63
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Abdelghany L, El-Mahdy N, Kawabata T, Goto S, Li TS. Dipyridamole induces the phosphorylation of CREB to promote cancer cell proliferation. Oncol Lett. 2021 Apr;21(4):251. doi: 10.3892/ol.2021.12512. Epub 2021 Feb 3. PMID: 33664815; PMCID: PMC7882894.
2. Wang JD, Wang YY, Lin SY, Chang CY, Li JR, Huang SW, Chen WY, Liao SL, Chen CJ. Exosomal HMGB1 Promoted Cancer Malignancy. Cancers (Basel). 2021 Feb 19;13(4):877. doi: 10.3390/cancers13040877. PMID: 33669632; PMCID: PMC7921955.
3. Alyasiry E, Janabi A, Hadi N. Dipyridamole ameliorates doxorubicin-induced cardiotoxicity. J Med Life. 2022 Sep;15(9):1184-1190. doi: 10.25122/jml-2021-0199. PMID: 36415530; PMCID: PMC9635225.
4. Esmaeili S, Azizian S, Shahmoradi B, Moradi S, Shahlaei M, Khodarahmi R. Dipyridamole inhibits α-amylase/α-glucosidase at sub-micromolar concentrations; in-vitro, in-vivo and theoretical studies. Bioorg Chem. 2019 Jul;88:102972. doi: 10.1016/j.bioorg.2019.102972. Epub 2019 May 6. PMID: 31078769.
In vitro protocol:
1. Abdelghany L, El-Mahdy N, Kawabata T, Goto S, Li TS. Dipyridamole induces the phosphorylation of CREB to promote cancer cell proliferation. Oncol Lett. 2021 Apr;21(4):251. doi: 10.3892/ol.2021.12512. Epub 2021 Feb 3. PMID: 33664815; PMCID: PMC7882894.
2. Wang JD, Wang YY, Lin SY, Chang CY, Li JR, Huang SW, Chen WY, Liao SL, Chen CJ. Exosomal HMGB1 Promoted Cancer Malignancy. Cancers (Basel). 2021 Feb 19;13(4):877. doi: 10.3390/cancers13040877. PMID: 33669632; PMCID: PMC7921955.
In vivo protocol:
1. Alyasiry E, Janabi A, Hadi N. Dipyridamole ameliorates doxorubicin-induced cardiotoxicity. J Med Life. 2022 Sep;15(9):1184-1190. doi: 10.25122/jml-2021-0199. PMID: 36415530; PMCID: PMC9635225.
2. Esmaeili S, Azizian S, Shahmoradi B, Moradi S, Shahlaei M, Khodarahmi R. Dipyridamole inhibits α-amylase/α-glucosidase at sub-micromolar concentrations; in-vitro, in-vivo and theoretical studies. Bioorg Chem. 2019 Jul;88:102972. doi: 10.1016/j.bioorg.2019.102972. Epub 2019 May 6. PMID: 31078769.
1: Ciacciarelli M, Zerbinati C, Violi F, Iuliano L. Dipyridamole: a drug with unrecognized antioxidant activity. Curr Top Med Chem. 2015;15(9):822-9. Review. PubMed PMID: 25697566.
2: Balakumar P, Nyo YH, Renushia R, Raaginey D, Oh AN, Varatharajan R, Dhanaraj SA. Classical and pleiotropic actions of dipyridamole: Not enough light to illuminate the dark tunnel? Pharmacol Res. 2014 Sep;87:144-50. doi: 10.1016/j.phrs.2014.05.008. Epub 2014 May 24. Review. PubMed PMID: 24861566.
3: Cullis PS, Watson D, Cameron A, McKee RF. Dipyridamole and paracetamol overdose resulting in multi-organ failure. Scott Med J. 2013 Aug;58(3):e14-7. doi: 10.1177/0036933013496926. Review. PubMed PMID: 23960064.
4: Dewilde S, Hawkins N. Investigating incoherence gives insight: clopidogrel is equivalent to extended-release dipyridamole plus aspirin in secondary stroke prevention. J Clin Epidemiol. 2012 Aug;65(8):835-45. doi: 10.1016/j.jclinepi.2012.01.019. Review. PubMed PMID: 22726765.
5: Eisert WG. Dipyridamole in antithrombotic treatment. Adv Cardiol. 2012;47:78-86. doi: 10.1159/000338053. Epub 2012 Aug 9. Review. PubMed PMID: 22906904.
6: Greenhalgh J, Bagust A, Boland A, Martin Saborido C, Oyee J, Blundell M, Dundar Y, Dickson R, Proudlove C, Fisher M. Clopidogrel and modified-release dipyridamole for the prevention of occlusive vascular events (review of Technology Appraisal No. 90): a systematic review and economic analysis. Health Technol Assess. 2011 Sep;15(31):1-178. doi: 10.3310/hta15310. Review. PubMed PMID: 21888837.
7: Melani A, Cipriani S, Corti F, Pedata F. Effect of intravenous administration of dipyridamole in a rat model of chronic cerebral ischemia. Ann N Y Acad Sci. 2010 Oct;1207:89-96. doi: 10.1111/j.1749-6632.2010.05732.x. Review. PubMed PMID: 20955431.
8: Pattillo CB, Fang K, Terracciano J, Kevil CG. Reperfusion of chronic tissue ischemia: nitrite and dipyridamole regulation of innate immune responses. Ann N Y Acad Sci. 2010 Oct;1207:83-8. doi: 10.1111/j.1749-6632.2010.05737.x. Review. PubMed PMID: 20955430; PubMed Central PMCID: PMC4414240.
9: d'Esterre CD, Lee TY. Effect of dipyridamole during acute stroke: exploring antithrombosis and neuroprotective benefits. Ann N Y Acad Sci. 2010 Oct;1207:71-5. doi: 10.1111/j.1749-6632.2010.05801.x. Review. PubMed PMID: 20955428.
10: Crown N, Mysak T. Safety of fixed-dose aspirin-extended-release dipyridamole in patients with ischemic heart disease. Am J Health Syst Pharm. 2010 May 1;67(9):728-33. doi: 10.2146/ajhp080645. Review. PubMed PMID: 20410547.
11: Bhavsar J, Rosenson RS. Adenosine transport, erythrocyte deformability and microvascular dysfunction: an unrecognized potential role for dipyridamole therapy. Clin Hemorheol Microcirc. 2010;44(3):193-205. doi: 10.3233/CH-2010-1274. Review. PubMed PMID: 20364065.
12: Salcedo J, Kern MJ. Effects of caffeine and theophylline on coronary hyperemia induced by adenosine or dipyridamole. Catheter Cardiovasc Interv. 2009 Oct 1;74(4):598-605. doi: 10.1002/ccd.22030. Review. PubMed PMID: 19496111.
13: Rouhl RP, Lodder J. ESPRIT: is aspirin plus dipyridamole superior to aspirin alone in TIA or minor stroke patients? Expert Rev Neurother. 2008 Nov;8(11):1661-5. doi: 10.1586/14737175.8.11.1661. Review. PubMed PMID: 18986236.
14: Chaturvedi S. Acetylsalicylic acid + extended-release dipyridamole combination therapy for secondary stroke prevention. Clin Ther. 2008 Jul;30(7):1196-205. Review. PubMed PMID: 18691981.
15: Kim HH, Liao JK. Translational therapeutics of dipyridamole. Arterioscler Thromb Vasc Biol. 2008 Mar;28(3):s39-42. doi: 10.1161/ATVBAHA.107.160226. Epub 2008 Jan 3. Review. PubMed PMID: 18174451; PubMed Central PMCID: PMC2615560.
16: Halkes PH, Algra A. Anticoagulants, aspirin and dipyridamole in the secondary prevention of cerebral ischaemia: which is the best for which patient? Cerebrovasc Dis. 2007;24 Suppl 1:107-11. Epub 2007 Nov 1. Review. PubMed PMID: 17971645.
17: De Schryver EL, Algra A, van Gijn J. Dipyridamole for preventing stroke and other vascular events in patients with vascular disease. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD001820. Review. PubMed PMID: 17636684.
18: Weyrich AS, Kraiss LW, Prescott SM, Zimmerman GA. New roles for an old drug: inhibition of gene expression by dipyridamole in platelet-leukocyte aggregates. Trends Cardiovasc Med. 2006 Apr;16(3):75-80. Review. PubMed PMID: 16546687.
19: Sudlow C. What is the role of dipyridamole in long-term secondary prevention after an ischemic stroke or transient ischemic attack? CMAJ. 2005 Oct 25;173(9):1024-6. Review. PubMed PMID: 16247094; PubMed Central PMCID: PMC1266320.
20: De Schryver EL, Algra A, van Gijn J. Cochrane review: dipyridamole for preventing major vascular events in patients with vascular disease. Stroke. 2003 Aug;34(8):2072-80. Epub 2003 Jul 10. Review. PubMed PMID: 12855826.
