Structure via PubChem · Public domain (PubChem)
vinpocetine
Sign in to saveAlso known as Apovincaminic acid ethyl ester, Eburnamenine-14-carboxylic acid, ethyl ester, (3α,16α)-, 1H-Indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine, eburnamenine-14-carboxylic acid deriv, Ethyl apovincaminate, Cavinton, RGH 4405, (+)-cis-Apovincaminic acid ethyl ester
Vinpocetine (ethyl apovincaminate), sold under the brand name Cavinton among others, is a synthetic derivative of the vinca alkaloid vincamine, differing by the removal of a hydroxyl group and by being the ethyl rather than the methyl ester of the underlying carboxylic acid. Vincamine is extracted from either the seeds of Voacanga africana or the leaves of Vinca minor (lesser periwinkle).
Chemical data
- Formula
- C22H26N2O2
- Molecular weight
- 350.5 g/mol
- IUPAC name
- ethyl (15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate
- SMILES
- CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC
- InChIKey
- DDNCQMVWWZOMLN-IRLDBZIGSA-N
- XLogP
- 4.1
- Polar surface area
- 34.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- Indications
- epilepsy, attention deficit hyperactivity disorder, diabetic nephropathy
via ChEMBL · EBI
Research
913 papers- Vinpocetine protects against osteoarthritis by inhibiting ferroptosis and extracellular matrix degradation via activation of the Nrf2/GPX4 pathway.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2024
- Vinpocetine (A comprehensive profile).Profiles of drug substances, excipients, and related methodology · 2022
- ALSUntangled 57: Vinpocetine.Amyotrophic lateral sclerosis & frontotemporal degeneration · 2021
- Vinpocetine. Monograph.Alternative medicine review : a journal of clinical therapeutic · 2002
- Vinpocetine, cognition, and epilepsy.Epilepsy & behavior : E&B · 2021
via PubMed
Wikidata facts
- Mass
- 350.199
- Has use
- medication
Show 8 more facts
- chemical formula
- C₂₂H₂₆N₂O₂
- canonical SMILES
- CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC
- subject has role
- nootropic
- isomeric SMILES
- CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC
- route of administration
- intravenous infusion and defusion
- medical condition treated
- vascular dementia
- Commons category
- Vinpocetine
- defined daily dose
- 15
via Wikidata · CC0
~5 min read
Encyclopedic overview
6 sectionsContents
- Medical uses
- Side effects
- Mechanism of action
- Dietary supplement
- Lawsuits
- References
Vinpocetine (ethyl apovincaminate), sold under the brand name Cavinton among others, is a synthetic derivative of the vinca alkaloid vincamine, differing by the removal of a hydroxyl group and by being the ethyl rather than the methyl ester of the underlying carboxylic acid. Vincamine is extracted from either the seeds of Voacanga africana or the leaves of Vinca minor (lesser periwinkle).
==Medical uses== Vinpocetine has been used in many Asian and European countries for treatment of cerebrovascular disorders such as stroke and dementia for over three decades.
Excerpted from Wikipedia’s “vinpocetine” article, available under the CC BY-SA 4.0 licence.