vinpocetine   Click here for help

GtoPdb Ligand ID: 5285

Approved drug PDB Ligand
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
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Summary of Clinical Use Click here for help
Vinpocetine is approved internationally, but use in the US is restricted to dietary supplements.
Vinpocetine is used to treat cerebrovascular disorders and age-related memory impairment. This is based on its reported ability to increase cerebral blood-flow [5] and produce a neuroprotective effect.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Inhibition of phosphodiesterase (PDE) type-1 by vinpocetine is believed to underlie its blood-flow enhancing effect [1,6]. The compound's neuroprotective effect is thought to be due to its Inhibition of voltage-sensitive Na+ channels [4].