dipyridamole   

GtoPdb Ligand ID: 4807

Synonyms: Persantine®
dipyridamole is an approved drug (FDA (1961))
Compound class: Synthetic organic
Comment: Dipyridamole is a phosphodiesterase (PDE) inhibitor.
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2D Structure
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Physico-chemical Properties
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
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
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
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).