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Dipyridamole

CAS No.
58-32-2
Chemical Name:
Dipyridamole
Synonyms
DIPYRIDAMOL;Dipiridamol;dypyridamole;Anginal;persantin;Persantine;Dipyrdamole;Dipyridamole (200 mg);ra8;RA 8
CBNumber:
CB6731869
Molecular Formula:
C24H40N8O4
Molecular Weight:
504.63
MDL Number:
MFCD00010555
MOL File:
58-32-2.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-06-03 11:24:09
Product description Number Pack Size Price
Dipyridamole ≥98% (HPLC) D9766 1g $39.4
Dipyridamole for peak identification European Pharmacopoeia (EP) Reference Standard Y0000802 2 mg $254
Dipyridamole European Pharmacopoeia (EP) Reference Standard D2850000 50 mg $167
Dipyridamole British Pharmacopoeia (BP) Reference Standard BP131 100MG $263
Dipyridamole impurity standard British Pharmacopoeia (BP) Reference Standard BP1102 25MG $238
More product size

Dipyridamole Properties

Melting point 165-166 °C (lit.)
Boiling point 593.96°C (rough estimate)
Density 1.2046 (rough estimate)
refractive index 1.6910 (estimate)
storage temp. room temp
solubility DMSO: soluble
form powder
pka pKa 6.4 (Uncertain)
color yellow
Water Solubility Soluble in chloroform, methanol, dilute acids, ethanol. Slightly soluble in water.
Merck 14,3346
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
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
SMILES C1(N(CCO)CCO)=NC(N2CCCCC2)=C2N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=N1
NCI Dictionary of Cancer Terms dipyridamole
FDA UNII 64ALC7F90C
NCI Drug Dictionary dipyridamole
ATC code B01AC07
NIST Chemistry Reference Pyrimidine, 2,6-bis(diethanolamino)-4,8-dipiperidino-pyrimido-(5,4-d)-(58-32-2)
UNSPSC Code 41116107
NACRES NA.77

Pharmacokinetic data

Protein binding 97-99%
Excreted unchanged in urine 1-5%
Volume of distribution 1.33-3.53(L/kg)
Biological half-life 9-12 / Unch

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
PPE dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  2
RTECS  KK7450000
HS Code  29335990
Storage Class 11 - Combustible Solids
Toxicity LD50 in rats: 8.4 g/kg orally; 208 mg/kg i.v. (Takenaka)
NFPA 704
0
2 0

Dipyridamole price More Price(108)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D9766 Dipyridamole ≥98% (HPLC) 58-32-2 1g $39.4 2026-04-30 Buy
Sigma-Aldrich Y0000802 Dipyridamole for peak identification European Pharmacopoeia (EP) Reference Standard 58-32-2 2 mg $254 2026-04-30 Buy
Sigma-Aldrich D2850000 Dipyridamole European Pharmacopoeia (EP) Reference Standard 58-32-2 50 mg $167 2026-04-30 Buy
Sigma-Aldrich BP131 Dipyridamole British Pharmacopoeia (BP) Reference Standard 58-32-2 100MG $263 2026-04-30 Buy
Sigma-Aldrich BP1102 Dipyridamole impurity standard British Pharmacopoeia (BP) Reference Standard 58-32-2 25MG $238 2026-04-30 Buy
Product number Packaging Price Buy
D9766 1g $39.4 Buy
Y0000802 2 mg $254 Buy
D2850000 50 mg $167 Buy
BP131 100MG $263 Buy
BP1102 25MG $238 Buy

Dipyridamole Chemical Properties,Uses,Production

Description

Dipyridamole (58-32-2) is a phosphodiesterase inhibitor (IC50=0.37, 0.38, 0.45, 0.9 and 4.5 μM for PDE11, 6, 10, 5 and 8 respectively.1,2 Potent equilibrative nucleoside transporter 1 (ENT1) inhibitor Ki=8.2 nM vs. 144.8 nM for ENT1 and ENT2 respectively.3 Antiplatelet activity.4

Chemical Properties

Yellow Powder

Originator

Persantine,Boehringer Ingelheim,US,1961

Uses

Selective inhibitor of phosphodiesterase V (PDE 5); potent coronary vasodilator drug; adenosine transport inhibitor; inhibitor of platelet aggregation

Uses

A phosphodiester, cGMP, and non-specific nucleoside transport inhibitor

Uses

Dipiridamol is known as a coronary vasodilating agent, although it also possesses specific antiaggregant activity. It is used for preventing thrombo-formation after cardiac valve replacement in combination with warfarin.

Uses

Dipyridamole prevents platelets sticking to the replacement heart valve and causing a blood clot on the valve. It is used to dilate blood vessels in people with peripheral arterial disease and coronary artery disease. This compound has been shown to suppress high glucose-induced osteopontin mRNA expression and protein secretion, as well as inhibit cAMP and cGMP hydrolysis. Research indicates that Dipyridamole is a non-specific nucleoside transport inhibitor with the ability to increase the effects of adenosine in sinoatrial and atrioventricular nodes. Dipyridamole is an inhibitor of ENT1 and ENT2.

Definition

ChEBI: A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.

Manufacturing Process

Urea may be reacted with acetoacetic ester and that product nitrated to give 5-nitro-orotec acid. That is hydrogenated, then reacted with urea and potassium cyanate to give tetrahydroxypyrimidopyrimidine. The tetrahydroxy compound is converted to the tetrachloro compound POCl3. Reaction with diethanolamine and then with piperidine gives dipyridamole.

brand name

Persantine (Boehringer Ingelheim).

Therapeutic Function

Coronary vasodilator

General Description

Dipyridamole, 2,2',2',2'''-[(4,8-di-1piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]-tetrakisethanol (Persantine), may be used for coronary andmyocardial insufficiency. Its biggest use today, however, isas an antithrombotic in patients with prosthetic heart valves.It is a bitter, yellow, crystalline powder, soluble in diluteacids, methanol, or chloroform. A formulation containingdipyridamole and aspirin (Aggrenox) is currently beingmarketed as an antithromobotic.
Dipyridamole is a long-acting vasodilator. Its vasodilatingaction is selective for the coronary system; it is indicatedfor long-term therapy of chronic angina pectoris. Thedrug also inhibits adenosine deaminase in erythrocytesand interferes with the uptake of the vasodilator adenosineby erythrocytes. These actions potentiate the effect ofprostacyclin (PGI2), which acts as an inhibitor to plateletaggregation.

Biological Activity

Coronary vasodilator; adenosine transport inhibitor. Phosphodiesterase inhibitor (IC 50 values are 0.37, 0.38, 0.45, 0.9 and 4.5 μ M for PDE11, 6, 10, 5 and 8 respectively).

Biochem/physiol Actions

Selective inhibitor of phosphodiesterase V (PDE 5); potent coronary vasodilator drug; adenosine transport inhibitor; inhibitor of platelet aggregation.

Mechanism of action

Dipyridamole exerts its antiplatelet function by increasing cellular concentrations of cAMP via its inhibition of the degradating enzyme, cyclic nucleotide PDE3. It also blocks adenosine uptake, which acts at A2 adenosine receptors to stimulate platelet adenyl cyclase. Less common uses for this drug include inhibition of embolization from prosthetic heart valves when used in combination with warfarin (the only currently recommended use) and reduction of thrombosis in patients with thrombotic disease when used in combination with aspirin. Alone, dipyridamole has little, if any, benefit in the treatment of thrombotic conditions.

Clinical Use

Dipyridamole is a pyrimidopyrimidine derivative with vasodilatory and antiplatelet properties.

Safety Profile

Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion and subcutaneous routes. Human systemic effects cardiomyopathy including infarction. Mutation data reported. Used as a coronary vasodilator. When heated to decomposition it e

Synthesis

Dipyridamole, 2,2',2'',2'''-[(4,8-dipiperidinopirimido[5,4-d]pirimidin-2,6- diyl)-diimino]-tetraethanol (19.4.13), is easily synthesized from 5-nitroorotic acid (19.4.8), easily obtained, in turn, by nitrating of 2,4-dihydroxy-6-methylpyrimidine, which is usually synthesized by the condensation of urea with acetoacetic ether. Reduction of the nitro group in 5-nitroorotic acid by various reducing agents gives 5-aminoorotic acid (19.4.9), which is reacted with urea or with potassium cyanide to give 2,4,6,8- tetrahydroxypyrimido[5,4-d]pyrimidine (19.4.10). This undergoes a reaction with a mixture of phosphorous oxychloride and phosphorous pentachloride, which forms 2,4,6,8- tetrachloropyrimido[ 5,4-d]pyrimidine (19.4.11). Reacting the resulting tetrachloride with piperidine replaces the chlorine atoms at C4 and C8 of the heterocyclic system with piperidine, giving 2,6-dichloropyrimido-4,8-dipiperidino[5,4-d]pyrimidine (19.4.12). Reacting the resulting product with diethanolamine gives dipyridamole (19.4.13).

Synthesis_58-32-2

Drug interactions

Potentially hazardous interactions with other drugs
Anti-arrhythmics: effects of adenosine enhanced and extended.
Anticoagulants: anticoagulant effect of coumarins, phenindione and heparin enhanced.

Metabolism

Dipyridamole is metabolised in the liver. Renal excretion of the parent compound is negligible (< 0.5%). Urinary excretion of the glucuronide metabolite is low (5%), the metabolites are mostly (about 95%) excreted via the bile into the faeces, with some evidence of entero-hepatic recirculation.

storage

Store at RT

References

[1] K FUJISHIGE. Cloning and characterization of a novel human phosphodiesterase that hydrolyzes both cAMP and cGMP (PDE10A).[J]. The Journal of Biological Chemistry, 1999, 274 26: 18438-18445. DOI:10.1074/jbc.274.26.18438
[2] S H SODERLING J A B S J Bayuga. Cloning and characterization of a cAMP-specific cyclic nucleotide phosphodiesterase.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1998, 95 15: 8991-8996. DOI:10.1073/pnas.95.15.8991
[3] WENWEI LIN  John K B. Synthesis, Flow Cytometric Evaluation, and Identification of Highly Potent Dipyridamole Analogues as Equilibrative Nucleoside Transporter 1 Inhibitors[J]. Journal of Medicinal Chemistry, 2007, 50 16: 3906-3920. DOI:10.1021/jm070311l
[4] COCCHERI S. Antiplatelet drugs–do we need new options With a reappraisal of direct thromboxane inhibitors.[J]. Drugs, 2010, 70 7: 887-908. DOI:10.2165/11536000-000000000-00000

7139-02-8
111-42-2
58-32-2
Synthesis of Dipyridamole from 2,6-Dichloro-4,8-dipiperidinopyrimidino[5,4-d]pyrimidine and Diethanolamine
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Dipyridamole (200 mg) 2,2',2'',2'''-((4,8-Di(piperidin-1-yl)pyrimido[5,4-d]-pyrimidine-2,6-diyl)bis(azanetriyl))tetraet Corosan Coroxin Curantyl Dipyridamine Dipyridan Dipyudamine Ethanol, 2,2',2'',2'''-(4,8-dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyldinitrilo)tetra- Ethanol, 2,2',2'',2'''-[(4,8-di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis- ethanol,2,2’,2’’,2’’’-((4,8-dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyl)din etraethanol Gulliostin itrilo)tetra- Justpertin Kurantil Natyl NSC-515776 Peridamol Permiltin Persantine Piroan Prandiol Prandiol 75 Protangix Pyrimido(5,4-d)pyrimidine, 2,6-bis(bis(2-hydroxyethyl)amino)-4,8-diperidino- Pyrimido(5,4-d)pyrimidine, 2,6-bis(bis(2-hydroxyethyl)amino)-4,8-dipiperidino- 2,2',2'',2'''-((4,8-Di(piperidin-1-yl)pyriMido[5,4-d]pyriMidine-2,6-diyl)bis(azanetriyl))tetraethanol DypyridaMole API 2,6-Bis(diethanolamine)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine 2,2',2'',2'''-[(4,8-Dipiperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakisethanol 2,6-BIS(DIETHANOLAMINE)-4,8-DIPIPERIDINOPYRIMIDO[5,4-D]PYRIMIDINE 2,6-bis(diethanolamino)-4,8-dipiperidinopyrimido-[5,4-d]pyrimidin 2,6-BIS(DIETHANOLAMINO)-4,8-DIPIPERIDINOPYRIMIDO[5,4-D]PYRIMIDINE 2,2',2'',2'''-4,8-DIPIPERIDINO-PYRIMIDO [5,4-D] PYRIMIDINE-2,6-DIYLDINITRILOTETRAETHANOL 2,2',2'',2'''-[(4,8-DIPIPERIDINYLPYRIMIDO[5,4-D]PYRIMIDINE-2,6-DIYL)DINITRILO]TETRAKISETHANOL persantin Dipyridamole (FDA) Dipyridamole,98% Dypyridamol DIPYRIDAMOLE CORONARY VASODILATOR DIPYRIDAMOLE,USP 2,2',2'',2'''-((4,8-Di(piperidin-1-yl)pyrimido[5,4-d]-pyrimidine-2,6-diyl)bis(azanetriyl))tetr 2,2',2'',2'''-[(4,8-Dipiperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetraethanol 2,2’,2’’,2’’’-(4,8-dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyldinitrilo)t 2,2’,2’’,2’’’-[(4,8-Di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakisethanol Agilease Anginal Apricor Cardioflux Cardoxil Chilcolan Cleridium Cleridium 150 cleridium150 Coribon Coridil Coronarine pyrimido(5,4-d)pyrimidine,2,6-bis(bis(2-hydroxyethyl)amino)-4,8-dipiperidino