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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26N2O2
Molecular Weight 350.454
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VINPOCETINE

SMILES

CCOC(=O)C1=C[C@]2(CC)CCCN3CCC4=C([C@H]23)N1C5=C4C=CC=C5

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

Molecular Formula C22H26N2O2
Molecular Weight 350.454
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including 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

Vinpocetine is a synthetic derivative of the vinca alkaloid vincamine. Vinpocetine was first isolated from the plant in 1975 by the Hungarian chemist Csaba Szántay. The mass production of the synthetic compound was started in 1978 by the Hungarian pharmaceutical company Richter Gedeon. Vinpocetine has been reported to have cerebral blood-flow enhancing and neuroprotective effects, and has been used as a drug in Eastern Europe for the treatment of cerebrovascular disorders and age-related memory impairment. Vinpocetine acts as a phosphodiesterase (PDE) type-1 inhibitor in isolated rabbit aorta, Independent of vinpocetine's action on PDE, vinpocetine inhibits IKK preventing IκB degradation and the following translocation of NF-κB to the cell nucleus. Increases in neuronal levels of DOPAC, a metabolic breakdown product of dopamine, have been shown to occur in striatal isolated nerve endings as a result of exposure to vinpocetine. Such an effect is consistent with the biogenic pharmacology of reserpine, a structural relative of vinpocetine. However, this effect tends to be reversible upon cessation of vinpocetine administration, with full remission typically occurring within 3–4 weeks. Vinpocetine is generally well-tolerated in humans. 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
14.0 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
[Blood flow insufficiency in vertebrobasilar system].
2003
[Myogenic effects of cyclic guanosine monophosphate in smooth muscle cells. Role of protein kinase C].
2003 Apr
Vinpocetine is a potent blocker of rat NaV1.8 tetrodotoxin-resistant sodium channels.
2003 Aug
[Studying cGMP-dependent mechanisms of vinpocetine effect on smooth muscle cells].
2003 Jul-Aug
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
[Neuroprotection strategies: effect of vinpocetine in vitro oxidative stress models].
2003 Nov-Dec
[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
Vinpocetine prevents 4-aminopyridine-induced changes in the EEG, the auditory brainstem responses and hearing.
2004 Dec
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
Vinpocetine blockade of sodium channels inhibits the rise in sodium and calcium induced by 4-aminopyridine in synaptosomes.
2005 Jun
[Drug therapy of female urinary incontinence].
2005 Mar
Effects of vinpocetine on the redistribution of cerebral blood flow and glucose metabolism in chronic ischemic stroke patients: a PET study.
2005 Mar 15
[11C]vinpocetine: a prospective peripheral benzodiazepine receptor ligand for primate PET studies.
2005 Mar 15
In vitro controlled release of vinpocetine-cyclodextrin-tartaric acid multicomponent complexes from HPMC swellable tablets.
2005 Mar 21
Spectrophotometric and liquid chromatographic determination of fenofibrate and vinpocetine and their hydrolysis products.
2005 May
Eburnamine derivatives and the brain.
2005 Nov
Acute and chronic effects of vinpocetine on cerebral hemodynamics and neuropsychological performance in multi-infarct patients.
2005 Sep
[Disturbances of brain metabolism in blood circulation disorders and their correction with cavinton].
2006
[The safe use of cavinton forte in discirculatory encephalopathy].
2006
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 was tested, cells were treated for approximately 24 h with vinpocetine and then, were simultaneously incubated in the presence of ABeta and the desired concentration of vinpocetine. The vehicle used for the treatment with vinpocetine (HC1 1 N, pH adjusted to 7.4 before use) was also included in control cultures. After an additional 24 h period the cells were analysed.
Substance Class Chemical
Created
by admin
on Wed Apr 02 06:53:09 GMT 2025
Edited
by admin
on Wed Apr 02 06:53:09 GMT 2025
Record UNII
543512OBTC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VINPOCETINE
DSC   EP   INN   JAN   MART.   MI   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
APOVINCAMINIC ACID ETHYL ESTER
Preferred 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
Vinpocetine [WHO-DD]
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
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
Classification Tree Code System Code
DSLD 724 (Number of products:364)
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
WHO-VATC QN06BX18
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
WHO-ATC N06BX18
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
NCI_THESAURUS C932
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
Code System Code Type Description
PUBCHEM
443955
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
EVMPD
SUB00070MIG
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
DAILYMED
543512OBTC
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
WIKIPEDIA
VINPOCETINE
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
FDA UNII
543512OBTC
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
NSC
760093
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
IUPHAR
5285
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
MESH
C013983
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
INN
4046
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
EPA CompTox
DTXSID5023740
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
DRUG CENTRAL
2828
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
ECHA (EC/EINECS)
256-028-0
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
ChEMBL
CHEMBL71752
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
RS_ITEM_NUM
1714608
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
CAS
42971-09-5
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
DRUG BANK
DB12131
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
SMS_ID
100000079134
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
RXCUI
24506
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C152887
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY
MERCK INDEX
m11458
Created by admin on Wed Apr 02 06:53:09 GMT 2025 , Edited by admin on Wed Apr 02 06:53:09 GMT 2025
PRIMARY Merck Index
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