Dipyridamole
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Dipyridamole
structure -
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CAS No:
58-32-2
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Formula:
C24H40N8O4
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Chemical Name:
Dipyridamole
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Synonyms:
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)dinitrilo]tetra-;Pyrimido[5,4-d]pyrimidine,ethanol deriv.;2,2′,2′′,2′′′-[(4,8-Di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis[ethanol];RA 8;2,6-Bis(diethanolamino)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine;2,2′,2′′,2′′′-[[4,8-Dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyl]dinitrilo]tetraethanol;Dipyridamine;Dipyridamol;Dipyridamole;Persantin;Persantine;Anginal;Cardoxin;Curantyl;Kurantil;Stenocardil;Apricor;Cardioflux;Stimolcardio;Coribon;Corosan;Coroxin;Prandiol;Coronarine;Cardoxil;Gulliostin;Protangix;Piroan;Peridamol;Natyl;Coridil;Cleridium;NSC 515776;Dipyridan;NSC 619103;2,2′,2′′,2′′′-[[4,8-Di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl]dinitrilo]tetraethanol;2,2′,2′′,2′′′-((4,8-Di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl)bis(azanetriyl))tetraethanol;2-([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;2-[[2-[Bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol
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Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs
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CAS No:
Description
Dipyridamole (Persantine) is a phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells.Target: Phosphodiesterase (PDE)Dipyridamole concentrations of 1 nmol/ml blood caused 90% inhibition of adenosine metabolism. Dipyridamole at therapeutic concentrations causes significant inhibition of adenosine metabolism in whole blood [1]. Dipyridamole has a dose-dependent inhibitory effect on thromboxane synthesis which was independen
Solid
Dipyridamole is 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. It has a role as an adenosine phosphodiesterase inhibitor, an EC 3.5.4.4 (adenosine deaminase) inhibitor, a platelet aggregation inhibitor and a vasodilator agent. It is a member of piperidines, a pyrimidopyrimidine, a tertiary amino compound and a tetrol.|A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752)|Dipyridamole is a Platelet Aggregation Inhibitor. The physiologic effect of dipyridamole is by means of Decreased Platelet Aggregation.|Dipyridamole is a vasodilator and inhibitor of platelet aggregation that is used to decrease the risk of thromboembolic complications and recurrence of stroke in patients known to have atherosclerotic cerebrovascular disease. Dipyridamole is associated with a low rate of serum enzyme elevations during treatment, but has not been linked to instances of clinically apparent acute liver injury.|Dipyridamole is a synthetic agent derivative of pyrimido-pyrimidine, with antiplatelet properties. Dipyridamole inhibits adenosine uptake by platelets and endothelial cells, triggering an accumulation of cyclic adenosine monophosphate (cAMP), and inhibiting the stimulation of platelet aggregation by agents such as platelet activating factor and collagen. (NCI04)
Dipyridamole Basic Attributes
504.63
504.63
200-374-7
64ALC7F90C
756743|619103|515776
DTXSID6040668
C445
B - Blood and blood forming organs
2933990090
Characteristics
145
0.7
yellow powder
1.4±0.1 g/cm3
163 °C
806.5°C at 760 mmHg
441.5±37.1 °C
1.670
soluble in chloroform, methanol, dilute acids, ethanol. Slightly soluble in water.DMSO: soluble
−20°C
LD50 in rats: 8.4 g/kg orally; 208 mg/kg i.v. (Takenaka)
227.5 Ų [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]|223.9 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Safety Information
NONH for all modes of transport
2
36/37/38
26-36
KK7450000
Xi
P305 + P351 + P338
H315-H319-H335
|Warning|H315 (99.26%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 136 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
Hypotension, if it occurs, is likely to be of short duration, but a vasopressor drug may be used if necessary. The oral LD50 in rats is greater than 6,000 mg/kg while in the dogs, the oral LD50 is approximately 400 mg/kg. LD50=8.4g/kg (orally in rat)
Dipyridamole has been associated with a low rate of serum enzyme elevations during therapy, but in large clinical trials the frequency of liver enzyme abnormalities was similar with dipyridamole therapy as with placebo. Cases of clinically apparent acute liver injury from dipyridamole have not been published although hepatitis is listed as a potential side effect in the product label. The clinical features of the liver injury linked to dipyridamole have not been described.
99%
Drug Information
For as an adjunct to coumarin anticoagulants in the prevention of postoperative thromboembolic complications of cardiac valve replacement and also used in prevention of angina.|FDA Label
Dipyridamole is a vasodilator and inhibitor of platelet aggregation that is used to decrease the risk of thromboembolic complications and recurrence of stroke in patients known to have atherosclerotic cerebrovascular disease. Dipyridamole is associated with a low rate of serum enzyme elevations during treatment, but has not been linked to instances of clinically apparent acute liver injury.
Antithrombotic Agents
Dipyridamole, a non-nitrate coronary vasodilator that also inhibits platelet aggregation, is combined with other anticoagulant drugs, such as warfarin, to prevent thrombosis in patients with valvular or vascular disorders. Dipyridamole is also used in myocardial perfusion imaging, as an antiplatelet agent, and in combination with aspirin for stroke prophylaxis.
Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)|Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases. (See all compounds classified as Phosphodiesterase Inhibitors.)|Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)
70%|Dipyridamole is metabolized in the liver to the glucuronic acid conjugate and excreted with the bile.|1 to 2.5 L/kg|2.3-3.5 mL/min/kg
hepatic
40 minutes
Dipyridamole likely inhibits both adenosine deaminase and phosphodiesterase, preventing the degradation of cAMP, an inhibitor of platelet function. This elevation in cAMP blocks the release of arachidonic acid from membrane phospholipids and reduces thromboxane A2 activity. Dipyridamole also directly stimulates the release of prostacyclin, which induces adenylate cyclase activity, thereby raising the intraplatelet concentration of cAMP and further inhibiting platelet aggregation.
Antistenocardin
Dipyridamole Use and Manufacturing
A phosphodiester, cGMP, and non-specific nucleoside transport inhibitor
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals
Computed Properties
Molecular Weight:504.6
XLogP3:0.7
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:12
Exact Mass:504.31725179
Monoisotopic Mass:504.31725179
Topological Polar Surface Area:145
Heavy Atom Count:36
Complexity:561
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Extract from the above information
Registered Holders
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QIDONG DONGYUE PHARMACEUTICAL CO LTD
Active
United States
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ALIVUS LIFE SCIENCES LTD
Active
United States
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MATRIX PHARMACORP PRIVATE LTD
Active
United States
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