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

Identification

Name
Vinpocetine
Accession Number
DB12131
Type
Small Molecule
Groups
Investigational
Description

Vinpocetine has been investigated for the treatment of Epilepsy.

Structure
Thumb
Synonyms
  • CERACTIN
  • ETHYL APOVINCAMIN-22-OATE
  • Vinpocetina
External IDs
AY-27255
Categories
UNII
543512OBTC
CAS number
42971-09-5
Weight
Average: 350.462
Monoisotopic: 350.199428085
Chemical Formula
C22H26N2O2
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of Vinpocetine can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Vinpocetine.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Vinpocetine is combined with 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Vinpocetine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineVinpocetine may increase the excretion rate of 3-isobutyl-1-methyl-7H-xanthine which could result in a lower serum level and potentially a reduction in efficacy.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Vinpocetine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Vinpocetine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Vinpocetine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Vinpocetine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Vinpocetine.
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
443955
PubChem Substance
347828430
ChemSpider
392007
BindingDB
50059033
ChEBI
32297
ChEMBL
CHEMBL71752
Wikipedia
Vinpocetine
ATC Codes
N06BX18 — Vinpocetine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2RecruitingTreatmentEpilepsies1
2, 3CompletedTreatmentImmunoregulation / Inflammatory Reaction / Strokes / Vinpocetine1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0fsi-1292000000-d2a82dd6f1fdac32445e

Taxonomy

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
Eburna alkaloid / Indolo[3,2-1de][1,5]naphthyridine / Beta-carboline / Pyridoindole / Diazanaphthalene / Alpha-amino acid or derivatives / Naphthyridine / 3-alkylindole / Indole / Indole or derivatives
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Enzymes

Kind
Protein
Organism
Human
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. [PubMed:22039822]

Drug created on October 20, 2016 15:24 / Updated on November 05, 2018 17:49