Dipyridamol

Dipyridamole

HCID 3108CAS 58-32-2

Grundinformationen

Standard-SMILES
OCCN(CCO)c1nc(N2CCCCC2)c2nc(N(CCO)CCO)nc(N3CCCCC3)c2n1
InChIKey
IZEKFCXSFNUWAM-UHFFFAOYSA-N
Summenformel
C24H40N8O4
Durchschnittliche Molmasse
504,6 g/mol
Monoisotopische Masse
504,31725176

Überblick

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 a vasodilator agent, a platelet aggregation inhibitor, an adenosine phosphodiesterase inhibitor and an EC 3.5.4.4 (adenosine deaminase) inhibitor. It is a member of piperidines, a tetrol, a pyrimidopyrimidine and a tertiary amino compound.

Namen und Bezeichner

Bevorzugter Name
Dipyridamole
IUPAC
2-[[2-[bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol
Lokaler Name
Dipyridamol
Englischer Name
Dipyridamole
Summenformel
C24H40N8O4
Molmasse
504.63

Namen und Synonyme

dipyridamole58-32-2PersantinDipyridaminePersantineCurantylDipyudamineDipiridamolCleridium 150DypyridamolIv PersantineDipyridamolum
Weitere Namen anzeigen
DIPYRIDAMOLdypyridamoleAnginalDipyrdamoleDipyridamole (200 mg)ra8RA 8
NSC-515776DTXSID604066864ALC7F90CB01AC07NSC5157762-({6-[bis(2-hydroxyethyl)amino]-4,8-bis(piperidin-1-yl)pyrimido[5,4-d][1,3]diazin-2-yl}(2-hydroxyethyl)amino)ethan-1-ol2-[[2-[bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanolCHEBI:4653

Datenbank-Bezeichner

CAS
58-32-2
PubChem CID
3108
DTXSID
DTXSID6040668
ChEMBL
CHEMBL932
ChEBI
CHEBI:4653
UNII
64ALC7F90C
EC Number
200-374-7
Nikkaji
J8.585E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,7
Polarare Oberfläche (TPSA)
145 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
12
Frei drehbare Bindungen
12
Schwere Atome
36

Experimentelle und physikochemische Eigenschaften

Drugs · 3 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals

LogP1.5
Solubility · 3 Einträge

Slightly

9.22e-01 g/L

10.7 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 4 Einträge

Breastfeeding; Lactation; Milk, Human; Phosphodiesterase Inhibitors; Vasodilator Agents; Platelet Aggregation Inhibitors

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Melting Point163 °C
Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
165 · 165-166 °C (lit.)
Siedepunkt
593.96 °C · 593.96°C (rough estimate)
Dichte
1.2046 · 1.2046 (rough estimate)
Brechungsindex
1.691 · 1.6910 (estimate)
storage temp.
room temp
Löslichkeit
DMSO: soluble

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H315 (98.7%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 75 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Other Safety InformationIMAP assessments - Ethanol, 2,2',2'',2'''-[(4,8-di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis-: Environment tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (98.7%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

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.

Adverse EffectsThe most frequently reported adverse effects include:
Toxicity SummarySigns and Symptoms of Overdose
Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Dipyridamole

Ambiguous-DILI-concern

3

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

wgk
2
hs_code
29335990
RTECS-Nr.
KK7450000
risk_code
36/37/38
Toxizität
LD50 in rats: 8.4 g/kg orally; 208 mg/kg i.v. (Takenaka)
hazard_code
Xi

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

B - Blood and blood forming organs

QB - Blood and blood forming organs

Protein Binding99%
Pharmacodynamics · 1 Eintrag

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.

Mechanism of Action · 1 Eintrag

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.

Biological Half-Life40 minutes
Metabolism/Metaboliteshepatic

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >10000
Use ClassificationPharmaceuticals
Anwendungen · 1 Eintrag

VerwendenDipyridamole 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.

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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.

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