vinpocetine   Click here for help

GtoPdb Ligand ID: 5285

Approved drug
vinpocetine is an approved drug
Compound class: Synthetic organic
Comment: Vinpocetine is a semisynthetic derivative of the vinca alkaloid vincamine [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 34.47
Molecular weight 350.2
XLogP 4.9
No. Lipinski's rules broken 0
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Canonical SMILES CCOC(=O)C1=CC2(CC)CCCN3C2c2n1c1ccccc1c2CC3
Isomeric SMILES CCOC(=O)C1=C[C@]2(CC)CCCN3[C@@H]2c2n1c1ccccc1c2CC3
InChI InChI=1S/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/t20-,22+/m1/s1
1. Hagiwara M, Endo T, Hidaka H. (1984)
Effects of vinpocetine on cyclic nucleotide metabolism in vascular smooth muscle.
Biochem. Pharmacol., 33 (3): 453-7. [PMID:6322804]
2. Loughney K, Martins TJ, Harris EA, Sadhu K, Hicks JB, Sonnenburg WK, Beavo JA, Ferguson K. (1996)
Isolation and characterization of cDNAs corresponding to two human calcium, calmodulin-regulated, 3',5'-cyclic nucleotide phosphodiesterases.
J. Biol. Chem., 271 (2): 796-806. [PMID:8557689]
3. Lörincz C, Szász K, Kisfaludy L. (1976)
The synthesis of ethyl apovincaminate.
Arzneimittelforschung, 26 (10a): 1907. [PMID:1037211]
4. Sitges M, Galván E, Nekrassov V. (2005)
Vinpocetine blockade of sodium channels inhibits the rise in sodium and calcium induced by 4-aminopyridine in synaptosomes.
Neurochem. Int., 46 (7): 533-40. [PMID:15843047]
5. Szilágyi G, Nagy Z, Balkay L, Boros I, Emri M, Lehel S, Márián T, Molnár T, Szakáll S, Trón L et al.. (2005)
Effects of vinpocetine on the redistribution of cerebral blood flow and glucose metabolism in chronic ischemic stroke patients: a PET study.
J. Neurol. Sci., 229-230: 275-84. [PMID:15760651]
6. Truss MC, Uckert S, Stief CG, Forssmann WG, Jonas U. (1996)
Cyclic nucleotide phosphodiesterase (PDE) isoenzymes in the human detrusor smooth muscle. II. Effect of various PDE inhibitors on smooth muscle tone and cyclic nucleotide levels in vitro.
Urol. Res., 24 (3): 129-34. [PMID:8839479]