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.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

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

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
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.
Blood, 125 (23): 3651-4. [PMID:25896650]
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]