Dipyridamole

Names

[ CAS No. ]:
58-32-2

[ Name ]:
Dipyridamole

[Synonym ]:
2,2',2'',2'''-[(4,8-Dipiperidin-1-ylpyrimido[5,4-d]pyrimidin-2,6-diyl)dinitrilo]tetraethanol
RA 8
Piroan
EINECS 200-374-7
Dipyridamole
Coridil
Dypyridamole
Apricor
Anginal
Natyl
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(1-piperidinyl)pyrimido[5,4-d]pyrimidine-2,6-diyl]dinitrilo}tetraethanol
Corosan
Coroxin
MFCD00010555
Ethanol, 2,2',2'',2'''-[(4,8-di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis-
Coribon

Biological Activity

[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 independent of aggregation. Dipyridamole also inhibited malonyldialdehyde production in response to both thrombin and arachidonic acid [2]. Dipyridamole enhances platelet inhibition by amplifying the signaling of the NO donor sodium nitroprusside. These data support the concept that enhancement of endothelium-dependent NO/cGMP-mediated signaling may be an important in vivo component of dipyridamole action [3].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE)

Research Areas >> Cardiovascular Disease

[References]

[1]. Klabunde, R.E., Dipyridamole inhibition of adenosine metabolism in human blood. Eur J Pharmacol, 1983. 93(1-2): p. 21-6.

[2]. Best, L.C., et al., Mode of action of dipyridamole on human platelets. Thromb Res, 1979. 16(3-4): p. 367-79.

[3]. Aktas, B., et al., Dipyridamole enhances NO/cGMP-mediated vasodilator-stimulated phosphoprotein phosphorylation and signaling in human platelets: in vitro and in vivo/ex vivo studies. Stroke, 2003. 34(3): p. 764-9.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
806.5±75.0 °C at 760 mmHg

[ Melting Point ]:
165-166ºC

[ Molecular Formula ]:
C₂₄H₄₀N₈O₄

[ Molecular Weight ]:
504.626

[ Flash Point ]:
441.5±37.1 °C

[ Exact Mass ]:
504.317261

[ PSA ]:
145.44000

[ LogP ]:
-1.22

[ Vapour Pressure ]:
0.0±3.0 mmHg at 25°C

[ Index of Refraction ]:
1.670

[ Storage condition ]:
−20°C

[ Water Solubility ]:
DMSO: soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KK7450000

CHEMICAL NAME :: Ethanol, 2,2',2'',2'''-((4,8-dipiperidinopyrimido(5,4-d)pyrimi dine-2,6-diyl)dinitri lo)tetra-

CAS REGISTRY NUMBER :: 58-32-2

BEILSTEIN REFERENCE NO. :: 0068373

LAST UPDATED :: 199612

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C24-H40-N8-O4

MOLECULAR WEIGHT :: 504.72

WISWESSER LINE NOTATION :: T66 BN DN GN INJ CCN HCN E- AT6NTJ B2Q F2Q& J- AT6NTJ B2Q F2Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 1429 ug/kg

TOXIC EFFECTS :: Cardiac - cardiomyopathy including infarction

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 1071 ug/kg

TOXIC EFFECTS :: Cardiac - cardiomyopathy including infarction

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 8400 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Behavioral - irritability

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1650 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Behavioral - ataxia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 195 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory depression Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2150 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2700 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: DNA inhibition

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - mouse Ascites tumor

DOSE/DURATION :: 60 umol/L

REFERENCE :: BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 22,2511,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5345 No. of Facilities: 154 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 2722 (estimated) No. of Female Employees: 1538 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
KK7450000

[ HS Code ]:
2933990090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Related Compounds

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