U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26N2O2
Molecular Weight 350.4549
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VINPOCETINE

SMILES

CC[C@]12CCCN3CCc4c5ccccc5n(C(=C1)C(=O)OCC)c4[C@]23[H]

InChI

InChIKey=DDNCQMVWWZOMLN-IRLDBZIGSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: http://www.rlsnet.ru/mnn_index_id_287.htm | https://www.ncbi.nlm.nih.gov/pubmed/11113577 | https://www.ncbi.nlm.nih.gov/pubmed/15887951 | https://www.ncbi.nlm.nih.gov/pubmed/11200083

No serious side effects have thus far been noted in clinical trials although none of these trials were long-term. Some users have reported headaches, especially at doses above 15 milligrams per day, as well as occasional upset stomach. The safety of vinpocetine in pregnant women has not been evaluated. Vinpocetine is not FDA approved in the United States for therapeutic use. The U.S. Food & Drug Administration (FDA) has ruled that vinpocetine, due to its synthetic nature and proposed therapeutic uses, was ineligible to be marketed as dietary supplement under the Federal Food, Drug, and Cosmetic Act (FDCA).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
14 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Cavinton

Approved Use

Vinpocetine is taken 3 times a day for 5-10 mg. The initial daily dose is 15 mg, the maximum is 30 mg. The drug in the form of injections is most often used in acute conditions in a single dose of 20 mg. With good tolerability for 3-4 days, the dose is increased to 1 mg / kg. The duration of therapy is 10-14 days. In the process of cancellation, the dosage of the drug should be reduced gradually. A year is allowed no more than 2-3 courses of taking the drug.
Primary
Cavinton

Approved Use

Vinpocetine is taken 3 times a day for 5-10 mg. The initial daily dose is 15 mg, the maximum is 30 mg. The drug in the form of injections is most often used in acute conditions in a single dose of 20 mg. With good tolerability for 3-4 days, the dose is increased to 1 mg / kg. The duration of therapy is 10-14 days. In the process of cancellation, the dosage of the drug should be reduced gradually. A year is allowed no more than 2-3 courses of taking the drug.
Primary
Cavinton

Approved Use

Vinpocetine is taken 3 times a day for 5-10 mg. The initial daily dose is 15 mg, the maximum is 30 mg. The drug in the form of injections is most often used in acute conditions in a single dose of 20 mg. With good tolerability for 3-4 days, the dose is increased to 1 mg / kg. The duration of therapy is 10-14 days. In the process of cancellation, the dosage of the drug should be reduced gradually. A year is allowed no more than 2-3 courses of taking the drug.
PubMed

PubMed

TitleDatePubMed
[Cerebral uptake and regional distribution of [11C]-vinpocetin after intravenous administration to healthy men: a PET study].
2002 Nov 24
[Blood flow insufficiency in vertebrobasilar system].
2003
[Cavinton prevention of neurosensory hypoacousis in patients with different forms of tuberculosis].
2003
Vinpocetine for cognitive impairment and dementia.
2003
[Myogenic effects of cyclic guanosine monophosphate in smooth muscle cells. Role of protein kinase C].
2003 Apr
The lowdown on Ginkgo biloba.
2003 Apr
Investigation and physicochemical characterization of vinpocetine-sulfobutyl ether beta-cyclodextrin binary and ternary complexes.
2003 Aug
Vinpocetine is a potent blocker of rat NaV1.8 tetrodotoxin-resistant sodium channels.
2003 Aug
Localization of cyclic nucleotide phosphodiesterase 2 in the brain-derived Triton-insoluble low-density fraction (raft).
2003 Feb
Implication of calmodulin-dependent phosphodiesterase type 1 during bovine sperm capacitation.
2003 Jan-Feb
[Studying cGMP-dependent mechanisms of vinpocetine effect on smooth muscle cells].
2003 Jul-Aug
Asymptomatic ischemic cerebrovascular disorders and neuroprotection with vinpocetine.
2003 May 20
Lipophilicity of vinpocetine and related compounds characterized by reversed-phase thin-layer chromatography.
2003 May 9
Physicochemical investigation of the effects of water-soluble polymers on vinpocetine complexation with beta-cyclodextrin and its sulfobutyl ether derivative in solution and solid state.
2003 Nov
[Human positron emission tomography with oral 11C-vinpocetine].
2003 Nov 16
[Use of instenon in complex treatment of patients with optic nerve atrophy caused by craniocerebral trauma].
2003 Nov-Dec
"Brain-specific" nutrients: a memory cure?
2003 Nov-Dec
[Memory and potassium channels].
2003 Oct-Dec
[Effect of vinpocetine on cerebral circulation in rats after exposure to radiation].
2003 Sep-Oct
Cyclic AMP-mediated regulation of striatal glutamate release: interactions of presynaptic ligand- and voltage-gated ion channels and G-protein-coupled receptors.
2003 Sep-Oct
[Use of cavinton in neuropaediatrics].
2004
Neuroprotection in ischemic/hypoxic disorders: from the preclinical to the clinical testing.
2004
Preparation and evaluation of microemulsion of vinpocetine for transdermal delivery.
2004 Apr
Cyclic nucleotide-dependent phosphodiesterases (PDEI) inhibition by muscarinic antagonists in bovine tracheal smooth muscle.
2004 Aug 15
Phosphodiesterase inhibition by a gastroprotective agent irsogladine: preferential blockade of cAMP hydrolysis.
2004 Aug 27
Identification, characterization and subcellular localization of TcPDE1, a novel cAMP-specific phosphodiesterase from Trypanosoma cruzi.
2004 Feb 15
Preparation, evaluation, and NMR characterization of vinpocetine microemulsion for transdermal delivery.
2004 Jul
The effect of citric acid added to hydroxypropyl methylcellulose (HPMC) matrix tablets on the release profile of vinpocetine.
2004 Jul
Vinpocetine inhibits the epileptic cortical activity and auditory alterations induced by pentylenetetrazole in the guinea pig in vivo.
2004 Jun
Review of phosphodiesterases in the urogenital system: new directions for therapeutic intervention.
2004 Nov
[Optimization of microemulsion containing vinpocetine and its physicochemical properties].
2004 Sep
Effects of various selective phosphodiesterase inhibitors on carbachol-induced contraction and cyclic nucleotide contents in guinea pig taenia coli.
2004 Sep
Pharmacokinetics and comparative bioavailability of two vinpocetine tablet formulations in healthy volunteers by using the metabolite apovincaminic acid as pharmacokinetic parameter.
2005
Neuroprotective activity of proproten in rats with experimental local photothrombosis of the prefrontal cortex.
2005 Apr
Increase in tumor oxygenation and potentiation of radiation effects using pentoxifylline, vinpocetine and ticlopidine hydrochloride.
2005 Dec
Expression and functional activity of phosphodiesterase type 5 in human and rabbit vas deferens.
2005 Feb
Multicomponent complex formation between vinpocetine, cyclodextrins, tartaric acid and water-soluble polymers monitored by NMR and solubility studies.
2005 Jan
cAMP phosphodiesterase inhibitors potentiate effects of prostacyclin analogs in hypoxic pulmonary vascular remodeling.
2005 Jan
Effects of various selective phosphodiesterase inhibitors on carbachol-induced contraction and cyclic nucleotide contents in the guinea pig gall bladder.
2005 Jul
[Drug therapy of female urinary incontinence].
2005 Mar
[11C]vinpocetine: a prospective peripheral benzodiazepine receptor ligand for primate PET studies.
2005 Mar 15
Spectrophotometric and liquid chromatographic determination of fenofibrate and vinpocetine and their hydrolysis products.
2005 May
Eburnamine derivatives and the brain.
2005 Nov
Inhibition of phosphodiesterase 1 augments the pulmonary vasodilator response to inhaled nitric oxide in awake lambs with acute pulmonary hypertension.
2006 Apr
Solid lipid nanoparticles for enhancing vinpocetine's oral bioavailability.
2006 Aug 10
New HPLC-MS method for quantitative determination of apovincaminic acid in human plasma.
2006 Feb
Restoration of neuronal plasticity by a phosphodiesterase type 1 inhibitor in a model of fetal alcohol exposure.
2006 Jan 18
Determination of apovincaminic acid in human plasma by high-performance liquid chromatography using solid-phase extraction and ultraviolet detection.
2006 Jan 18
Single and combined effects of carbamazepine and vinpocetine on depolarization-induced changes in Na+, Ca2+ and glutamate release in hippocampal isolated nerve endings.
2006 Jul
Herbal medicine in the treatment of Alzheimer's disease.
2006 Mar-Apr
Patents

Sample Use Guides

In Vivo Use Guide
Follow the suggested manufacturers' guidelines. Most clinical studies used vinpocetine 10 mg 3 times daily orally or parenterally.
Route of Administration: Other
The cytoprotective effect of vinpocetine was investigated on PC12 cells treated with the amyloid-beta-peptides for 24 hours. PC12 cells were incubated, during 24 hours, with the desired concentration of ABeta peptides, Abeta25-35 and ABeta1-40, or with the corresponding reverse sequences, ABeta35-25 and ABeta40-1, in RPMI 1640 supplemented with 15% serum. When the protective effect of vinpocetine
Name Type Language
VINPOCETINE
DSC   EP   INN   JAN   MART.   MI   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
VINPOCETINE [DSC]
Common Name English
NSC-760093
Code English
VINPOCETINE [MART.]
Common Name English
VINPOCETINE [USAN]
Common Name English
TCV 3B
Common Name English
VINPOCETINE [VANDF]
Common Name English
CAVINTON
Common Name English
VINPOCETINE [MI]
Common Name English
CIS-APOVINCAMINIC ACID ETHYL ESTER
Common Name English
RGH 4405
Common Name English
CERACTIN
Common Name English
VINPOCETINE [USP-RS]
Common Name English
ETHYL APOVINCAMIN-22-OATE
Common Name English
VINPOCETINE [INN]
Common Name English
APOVINCAMINIC ACID ETHYL ESTER
Common Name English
EBURNAMENINE 14-CARBOXYLIC ACID ETHYL ESTER (3.ALPHA.,16.ALPHA.)
Common Name English
AY-27255
Code English
ETHYL (+)-CIS-APOVINCAMINATE
Common Name English
VINPOCETINE [EP MONOGRAPH]
Common Name English
VINPORAL
Common Name English
ULTRA-VINCA
Common Name English
BRAVINTON
Common Name English
AY-27,255
Code English
VINPOCETINE [JAN]
Common Name English
VINPOCETINE [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 724 (Number of products:364)
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
WHO-VATC QN06BX18
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
WHO-ATC N06BX18
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
NCI_THESAURUS C932
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
Code System Code Type Description
PUBCHEM
443955
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY
EVMPD
SUB00070MIG
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY
WIKIPEDIA
VINPOCETINE
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY
FDA UNII
543512OBTC
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY
USP_CATALOG
1714608
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY USP-RS
IUPHAR
5285
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY
MESH
C013983
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY
INN
4046
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY
EPA CompTox
42971-09-5
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY
DRUG CENTRAL
2828
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY
ECHA (EC/EINECS)
256-028-0
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY
ChEMBL
CHEMBL71752
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY
CAS
42971-09-5
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY
DRUG BANK
DB12131
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY
RXCUI
24506
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C152887
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY
MERCK INDEX
M11458
Created by admin on Fri Jun 25 21:16:44 UTC 2021 , Edited by admin on Fri Jun 25 21:16:44 UTC 2021
PRIMARY Merck Index