Dipyridamole

Base Information

• Chemical Name: Dipyridamole
• CAS No.: 58-32-2
• Molecular Formula: C24H40N8O4
• Molecular Weight: 504.633
• Hs Code.: 29335990
• European Community (EC) Number: 200-374-7
• NSC Number: 756743,619103,515776
• UNII: 64ALC7F90C
• DSSTox Substance ID: DTXSID6040668
• Nikkaji Number: J8.585E
• Wikipedia: Dipyridamole
• Wikidata: Q419374
• NCI Thesaurus Code: C445
• RXCUI: 3521
• Pharos Ligand ID: JSHXM1LT6W7V
• Metabolomics Workbench ID: 43229
• ChEMBL ID: CHEMBL932
• Mol file: 58-32-2.mol

Synonyms:Antistenocardin;Apo Dipyridamole;Apo-Dipyridamole;Cerebrovase;Cléridium;Curantil;Curantyl;Dipyramidole;Dipyridamole;Kurantil;Miosen;Novo Dipiradol;Novo-Dipiradol;Persantin;Persantine

Chemical Property of Dipyridamole

Chemical Property:

• Appearance/Colour: Yellow Powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 165-166 °C(lit.)
• Refractive Index: 1.666
• Boiling Point: 806.5 °C at 760 mmHg
• PKA: pKa 6.4 (Uncertain)
• Flash Point: 441.5 °C
• PSA: 145.44000
• Density: 1.352 g/cm³
• LogP: 0.11240
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble
• Water Solubility.: Soluble in chloroform, methanol, dilute acids, ethanol. Slightly soluble in water.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 12
• Exact Mass: 504.31725179
• Heavy Atom Count: 36
• Complexity: 561

Purity/Quality:

98.5%, ^*data from raw suppliers

Dipyridamole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antithrombotic Agents
• Canonical SMILES: C1CCN(CC1)C2=NC(=NC3=C2N=C(N=C3N4CCCCC4)N(CCO)CCO)N(CCO)CCO
• Recent ClinicalTrials: BROKEN-SWEDEHEART-Optimized Pharmacological Treatment for Broken Heart (Takotsubo) Syndrome
• Recent EU Clinical Trials: Optimized pharmacological treatment for broken heart (takotsubo) syndrome
• Recent NIPH Clinical Trials: Long-term therapeutic effect of pioglitazone on chronic kidney disease (CKD)
• 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
• 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. 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. Selective inhibitor of phosphodiesterase V (PDE 5); potent coronary vasodilator drug; adenosine transport inhibitor; inhibitor of platelet aggregation A phosphodiester, cGMP, and non-specific nucleoside transport inhibitor
• Therapeutic Function: Coronary vasodilator
• Clinical Use: Dipyridamole is a pyrimidopyrimidine derivative with vasodilatory and antiplatelet properties.
• Drug interactions: Potentially hazardous interactions with other drugsAnti-arrhythmics: effects of adenosine enhanced and extended.Anticoagulants: anticoagulant effect of coumarins, phenindione and heparin enhanced.

Technology Process of Dipyridamole

There total 12 articles about Dipyridamole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2,6-dichloro-4,8-bis(piperidin-1-yl)pyrimido[5,4-d]pyrimidine (7139-02-8) + 2,2'-iminobis[ethanol] (111-42-2) → dipyridamole (58-32-2)

Guidance literature:

2,6-dichloro-4,8-bis(piperidin-1-yl)pyrimido[5,4-d]pyrimidine; 2,2'-iminobis[ethanol]; In toluene; at 0 - 155 ℃; for 9.5h;

With benzenesulfonic acid; In water; toluene; at 0 - 95 ℃; for 2h;

With ammonia; pyrographite; In ethanol; for 0.333333h; pH=8; Temperature;

Reference yield: 50.31%

C16H24N6O2 + 2,2'-iminobis[ethanol] (111-42-2) → dipyridamole (58-32-2)

Guidance literature:

With hydrogen; at 240 ℃; for 3h; under 11251.1 Torr;

Reference yield:

2,2'-(6-chloro-4,8-di-piperidin-1-yl-pyrimido[5,4-d]pyrimidin-2-ylazanediyl)-bis-ethanol (54093-92-4) + 2,2'-iminobis[ethanol] (111-42-2) → dipyridamole (58-32-2)

Guidance literature:

at 25 - 115 ℃;

upstream raw materials:

2,6-dichloro-4,8-bis(piperidin-1-yl)pyrimido[5,4-d]pyrimidine

2,2'-iminobis[ethanol]

piperidine

2,4,6,8-Tetrachloro-pyrimido[5,4-d]pyrimidine

Downstream raw materials:

dipyridamole di-p-toluenesulfonate

Refernces

• 1、 -. "Production method of dipyridamole bulk drug". Paragraph 0005; 0017. . Retrieved 2018/06/04.
• 2、 -. "Novel technology with introduced catalyst to optimize synthesis of dipyridamole". Paragraph 0038; 0039; 0040. . Retrieved 2017/08/31.