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
References
1. Daniels G, Ballif BA, Helias V, Saison C, Grimsley S, Mannessier L, Hustinx H, Lee E, Cartron JP, Peyrard T et al.. (2015)
Lack of the nucleoside transporter ENT1 results in the Augustine-null blood type and ectopic mineralization.
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2. Fisher DA, Smith JF, Pillar JS, St Denis SH, Cheng JB. (1998)
Isolation and characterization of PDE8A, a novel human cAMP-specific phosphodiesterase.
Biochem Biophys Res Commun, 246 (3): 570-7. [PMID:9618252]
3. Gardner C, Robas N, Cawkill D, Fidock M. (2000)
Cloning and characterization of the human and mouse PDE7B, a novel cAMP-specific cyclic nucleotide phosphodiesterase.
Biochem Biophys Res Commun, 272 (1): 186-92. [PMID:10872825]
4. Grañe-Boladeras N, Williams D, Tarmakova Z, Stevanovic K, Villani LA, Mehrabi P, Siu KWM, Pastor-Anglada M, Coe IR. (2019)
Oligomerization of equilibrative nucleoside transporters: a novel regulatory and functional mechanism involving PKC and PP1.
FASEB J, 33 (3): 3841-3850. [PMID:30521377]
5. Hammond JR, Archer RG. (2004)
Interaction of the novel adenosine uptake inhibitor 3-[1-(6,7-diethoxy-2-morpholinoquinazolin-4-yl)piperidin-4-yl]-1,6-dimethyl-2,4(1H,3H)-quinazolinedione hydrochloride (KF24345) with the es and ei subtypes of equilibrative nucleoside transporters.
J Pharmacol Exp Ther, 308 (3): 1083-93. [PMID:14634039]
6. Hayashi M, Matsushima K, Ohashi H, Tsunoda H, Murase S, Kawarada Y, Tanaka T. (1998)
Molecular cloning and characterization of human PDE8B, a novel thyroid-specific isozyme of 3',5'-cyclic nucleotide phosphodiesterase.
Biochem Biophys Res Commun, 250 (3): 751-6. [PMID:9784418]
7. Sasaki T, Kotera J, Yuasa K, Omori K. (2000)
Identification of human PDE7B, a cAMP-specific phosphodiesterase.
Biochem Biophys Res Commun, 271 (3): 575-83. [PMID:10814504]
8. Sundaram M, Yao SY, Ng AM, Griffiths M, Cass CE, Baldwin SA, Young JD. (1998)
Chimeric constructs between human and rat equilibrative nucleoside transporters (hENT1 and rENT1) reveal hENT1 structural domains interacting with coronary vasoactive drugs.
J Biol Chem, 273 (34): 21519-25. [PMID:9705281]
9. Wang C, Lin W, Playa H, Sun S, Cameron K, Buolamwini JK. (2013)
Dipyridamole analogs as pharmacological inhibitors of equilibrative nucleoside transporters. Identification of novel potent and selective inhibitors of the adenosine transporter function of human equilibrative nucleoside transporter 4 (hENT4).
Biochem Pharmacol, 86 (11): 1531-40. [PMID:24021350]
10. Warraich S, Bone DB, Quinonez D, Ii H, Choi DS, Holdsworth DW, Drangova M, Dixon SJ, Séguin CA, Hammond JR. (2013)
Loss of equilibrative nucleoside transporter 1 in mice leads to progressive ectopic mineralization of spinal tissues resembling diffuse idiopathic skeletal hyperostosis in humans.
J Bone Miner Res, 28 (5): 1135-49. [PMID:23184610]
11. Wright NJ, Lee SY. (2019)
Structures of human ENT1 in complex with adenosine reuptake inhibitors.
Nat Struct Mol Biol, 26 (7): 599-606. [PMID:31235912]
12. Yao SY, Ng AM, Cass CE, Baldwin SA, Young JD. (2011)
Nucleobase transport by human equilibrative nucleoside transporter 1 (hENT1).
J Biol Chem, 286 (37): 32552-62. [PMID:21795683]