dipyridamole   Click here for help

GtoPdb Ligand ID: 4807

Synonyms: Persantine®
Approved drug PDB Ligand
dipyridamole is an approved drug (FDA (1961))
Compound class: Synthetic organic
Comment: Dipyridamole is a phosphodiesterase (PDE) inhibitor.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: dipyridamole, dipyridamole

dipyridamole is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 12
Hydrogen bond donors 4
Rotatable bonds 12
Topological polar surface area 145.44
Molecular weight 504.32
XLogP 1.76
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OCCN(c1nc(N2CCCCC2)c2c(n1)c(nc(n2)N(CCO)CCO)N1CCCCC1)CCO
Isomeric SMILES OCCN(c1nc(N2CCCCC2)c2c(n1)c(nc(n2)N(CCO)CCO)N1CCCCC1)CCO
InChI 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
No information available.
Summary of Clinical Use Click here for help
Dipyridamole is a drug used as an anticoagulant adjuvant to prevent thrombotic complications following cardiac valve replacement surgery. Dipyridamole is also used as a treatment to help prevent angina.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Dipyridamole is primarily a phosphodiesterase inhibitor, but also shows inhibitory activity against the equilibrative nucleoside transporter (eg SLC29A1). By inhibiting phosphodiesterase, dipyridamole raises cAMP levels, blocking the release of arachidonic acid from membrane phospholipids and reducing thromboxane A2 activity; effects which combine to inhibit platelet function. Dipyridamole further inhibits platelet aggregation by directly stimulating the release of prostacyclin, which also increases platelet cAMP levels (inhibits platelet function).