CAS 58-32-2|Dipyridamole

Introduction：Basic information about CAS 58-32-2|Dipyridamole, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Dipyridamole BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles119
8. Synonyms

Common Name	Dipyridamole
CAS Number	58-32-2	Molecular Weight	504.626
Density	1.4±0.1 g/cm3	Boiling Point	806.5±75.0 °C at 760 mmHg
Molecular Formula	C₂₄H₄₀N₈O₄	Melting Point	165-166ºC
MSDS	ChineseUSA	Flash Point	441.5±37.1 °C
Symbol	GHS07	Signal Word	Warning

Names

Name	dipyridamole
Synonym	More Synonyms

Dipyridamole BiologicalActivity

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.

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.

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
InChIKey	IZEKFCXSFNUWAM-UHFFFAOYSA-N
SMILES	OCCN(CCO)c1nc(N2CCCCC2)c2nc(N(CCO)CCO)nc(N3CCCCC3)c2n1
Storage condition	−20°C
Water Solubility	DMSO: soluble

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

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%

Articles119

Hypoxanthine uptake by skeletal muscle microvascular endothelial cells from equilibrative nucleoside transporter 1 (ENT1)-null mice: effect of oxidative stress.

Microvasc. Res. 98 , 16-22, (2015)

Adenosine is an endogenous regulator of vascular tone. This activity of adenosine is terminated by its uptake and metabolism by microvascular endothelial cells (MVEC). The predominant transporter invo...

Oxidative stress modulates nucleobase transport in microvascular endothelial cells

Microvasc. Res. 95 , 68-75, (2014)

Purine nucleosides and nucleobases play key roles in the physiological response to vascular ischemia/reperfusion events. The intra- and extracellular concentrations of these compounds are controlled, ...

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Synonyms

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

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