NAV

Vinpocetine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Vinpocetine is a synthetic derivative of a vinca alkaloid used to treat neurological symptoms of cerebrovascular disease.

Generic Name
Vinpocetine
DrugBank Accession Number
DB12131
Background

Vinpocetine has been investigated for the treatment of Epilepsy.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 350.462
Monoisotopic: 350.199428085
Chemical Formula
C22H26N2O2
Synonyms
  • CERACTIN
  • ETHYL APOVINCAMIN-22-OATE
  • Vinpocetina
  • Vinpocetine
External IDs
  • AY-27255
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Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofCerebrovascular stenosis••••••••••••
Symptomatic treatment ofNeurological disorders••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Vinpocetine is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Vinpocetine can be increased when it is combined with Abametapir.
AcarboseThe risk or severity of hypoglycemia can be increased when Vinpocetine is combined with Acarbose.
AcebutololAcebutolol may increase the arrhythmogenic activities of Vinpocetine.
AceclofenacThe risk or severity of hyperkalemia can be increased when Aceclofenac is combined with Vinpocetine.
Food Interactions
Not Available

Products

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Categories

ATC Codes
N06BX18 — Vinpocetine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as eburnan-type alkaloids. These are alkaloids with a structure based on the eburnan skeleton, that arises from rearrangement of the aspidospermidine ring system, involving migration of C-21 from C-7 to C-2, fission of the 2,16-bond, and attachment of C-16 to N-1.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Eburnan-type alkaloids
Sub Class
Not Available
Direct Parent
Eburnan-type alkaloids
Alternative Parents
Indolonaphthyridine alkaloids / Beta carbolines / 3-alkylindoles / Alpha amino acids and derivatives / Naphthyridines / Aralkylamines / Piperidines / Benzenoids / Pyrroles / Heteroaromatic compounds
show 8 more
Substituents
3-alkylindole / Alpha,beta-unsaturated carboxylic ester / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Beta-carboline
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
543512OBTC
CAS number
42971-09-5
InChI Key
DDNCQMVWWZOMLN-IRLDBZIGSA-N
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
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
[H][C@]12N3CCC[C@@]1(CC)C=C(N1C4=CC=CC=C4C(CC3)=C21)C(=O)OCC

References

General References
  1. FDA Thailand Product Information: Cavinton (vinpocetine) for oral use [Link]
PubChem Compound
443955
PubChem Substance
347828430
ChemSpider
392007
BindingDB
50059033
RxNav
24506
ChEBI
32297
ChEMBL
CHEMBL71752
ZINC
ZINC000019796031
PDBe Ligand
T7F
Wikipedia
Vinpocetine
PDB Entries
8i5x

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2, 3CompletedTreatmentImmunoregulation / Inflammation / Stroke / Vinpocetine1
1, 2SuspendedTreatmentEpilepsy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionParenteral20.000 mg
TabletOral10 mg
TabletOral5 mg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0254 mg/mLALOGPS
logP4.35ALOGPS
logP4.07Chemaxon
logS-4.1ALOGPS
pKa (Strongest Basic)6.94Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area34.47 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity104.24 m3·mol-1Chemaxon
Polarizability40.31 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0fsi-1292000000-d2a82dd6f1fdac32445e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f6t-0009000000-379bae5189f41bb1c0ff
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-f592d0d2d5de6952238b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pb9-0009000000-d37c0354046cbf6e3dee
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0019000000-ab2d92014693e8731eb4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pb9-0094000000-7af1242a858399c309b0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004j-0090000000-bd38a60eb6d8ec726f9d
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-192.5003072
predicted
DarkChem Lite v0.1.0
[M-H]-186.19145
predicted
DeepCCS 1.0 (2019)
[M+H]+193.4916072
predicted
DarkChem Lite v0.1.0
[M+H]+188.54944
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.0215072
predicted
DarkChem Lite v0.1.0
[M+Na]+194.6426
predicted
DeepCCS 1.0 (2019)

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [Article]

Drug created at October 20, 2016 21:24 / Updated at May 21, 2021 10:22