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D9766

Sigma-Aldrich

Dipyridamole

≥98% (HPLC), powder, phosphodiesterase V inhibitor

Synonym(s):

NSC 515776, NSC 619103

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About This Item

Empirical Formula (Hill Notation):
C24H40N8O4
CAS Number:
58-32-2
Molecular Weight:
504.63
EC Number:
200-374-7
MDL number:
MFCD00010555
UNSPSC Code:
41106305
PubChem Substance ID:
24277705
NACRES:
NA.77

product name

Dipyridamole, ≥98% (HPLC)

Quality Level

200

Assay

≥98% (HPLC)

form

powder

color

yellow

mp

165-166 °C (lit.)

solubility

DMSO: soluble
ethanol: soluble

originator

Boehringer Ingelheim

storage temp.

room temp

SMILES string

OCCN(CCO)c1nc(N2CCCCC2)c3nc(nc(N4CCCCC4)c3n1)N(CCO)CCO

InChI

1S/C24H40N8O4/c33-15-11-31(12-16-34)23-26-20-19(21(27-23)29-7-3-1-4-8-29)25-24(32(13-17-35)14-18-36)28-22(20)30-9-5-2-6-10-30/h33-36H,1-18H2

InChI key

IZEKFCXSFNUWAM-UHFFFAOYSA-N

Gene Information

human ... CYP1A2(1544) , PDE10A(10846) , PDE1A(5136) , PDE1B(5153) , PDE1C(5137) , PDE2A(5138) , PDE3A(5139) , PDE3B(5140) , PDE4A(5141) , PDE4B(5142) , PDE4C(5143) , PDE4D(5144) , PDE5A(8654) , PDE6A(5145) , PDE6B(5158) , PDE6C(5146) , PDE6D(5147) , PDE6G(5148) , PDE6H(5149) , PDE7A(5150) , PDE7B(27115) , PDE8A(5151) , PDE8B(8622) , PDE9A(5152) , SLC29A1(2030)
mouse ... Slc29a1(63959)

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General description

Dipyridamole prevents cellular uptake of adenosine. It functions as an equilibrative nucleoside transporter 1 (ENT1) inhibitor.

Application

Dipyridamole has been used:
  • to perform in vitro growth inhibition assay(40)
  • to determine its ability to prevent uterine myometrial contractions(41)
  • to determine its effects on nicotinamide adenine dinucleotide (NAD+)-induced increase in intracellular adenosine triphosphate (ATP) levels(42)
  • to prevent nicotinamide riboside (NR)-induced axonal protection(43)

Biochem/physiol Actions

Selective inhibitor of phosphodiesterase V (PDE 5); potent coronary vasodilator drug; adenosine transport inhibitor; inhibitor of platelet aggregation.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Phosphodiesterases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Boehringer Ingelheim. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Extracellular Degradation into Adenosine and the Activities of Adenosine Kinase and AMPK Mediate Extracellular NAD+-produced increases in the Adenylate Pool of BV2 Microglia under Basal Conditions
Zhang J, et al.
Frontiers in Cellular Neuroscience, 12 (2018)
J A Thorn et al.
General pharmacology, 27(4), 613-620 (1996-06-01)
1. In mammals, nucleoside transport is an important determinant of the pharmacokinetics, plasma and tissue concentration, disposition and in vivo biological activity of adenosine as well as nucleoside analogues used in antiviral and anticancer therapies. 2. Two broad types of
Nyoli Valentine et al.
The Cochrane database of systematic reviews, 11, CD005449-CD005449 (2012-11-16)
Cardiovascular disease (CVD) is the most prevalent complication of type 2 diabetes with an estimated 65% of people with type 2 diabetes dying from a cause related to atherosclerosis. Adenosine-diphosphate (ADP) receptor antagonists like clopidogrel, ticlopidine, prasugrel and ticagrelor impair
M Sundaram et al.
The Journal of biological chemistry, 273(34), 21519-21525 (1998-08-15)
We have recently isolated cDNAs from human placenta and rat jejunum encoding the prototypic human and rat equilibrative nitrobenzylthioinosine (NBMPR)-sensitive nucleoside transporters hENT1 and rENT1. The two proteins (456 and 457 residues, Mr 50,000) are 78% identical in amino acid
Terence B Beghyn et al.
Journal of medicinal chemistry, 54(9), 3222-3240 (2011-04-21)
The dominant strategy for discovery of new antimalarial drugs relies on cell-free assays on specific biochemical pathways of Plasmodium falciparum . However, it appears that screening directly on the parasite is a more rewarding approach. The "drug to genome to
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