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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

[H][C@]12N3CCC[C@@]1(CC)C=C(N4C5=C(C=CC=C5)C(CC3)=C24)C(=O)OCC

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
[Neuroprotective effects of vinpocetine in vivo and in vitro. Apovincaminic acid derivatives as potential therapeutic tools in ischemic stroke].
2002
[Investigation of vasoactive agents with indole skeletons at Richter Ltd].
2002
Drug distribution in man: a positron emission tomography study after oral administration of the labelled neuroprotective drug vinpocetine.
2002 Aug
PET studies on the brain uptake and regional distribution of [11C]vinpocetine in human subjects.
2002 Dec
Effect of inhibitors of cyclic nucleotide phosphodiesterases on electrical and contractile activity of smooth muscle cells.
2002 Jan
Vinpocetine. Monograph.
2002 Jun
The effect of phosphodiesterase inhibition on gallbladder motility in vitro.
2002 Jun 15
Piracetam and vinpocetine exert cytoprotective activity and prevent apoptosis of astrocytes in vitro in hypoxia and reoxygenation.
2002 May
[Cerebral uptake and regional distribution of [11C]-vinpocetin after intravenous administration to healthy men: a PET study].
2002 Nov 24
Cerebral uptake of [ethyl-11C]vinpocetine and 1-[11C]ethanol in cynomolgous monkeys: a comparative preclinical PET study.
2002 Oct
Selective suppression of the slow-inactivating potassium currents by nootropics in molluscan neurons.
2002 Sep
[Blood flow insufficiency in vertebrobasilar system].
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
Large-conductance Ca2+- activated K+ channels:physiological role and pharmacology.
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
A vinca alkaloid enhances morphological dynamics of dendritic spines of neocortical layer 2/3 pyramidal cells.
2003 Jan 15
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
[Effect of vinpocetin on the hemorheologic parameters in patients with chronic cerebrovascular disease].
2003 May 18
Asymptomatic ischemic cerebrovascular disorders and neuroprotection with vinpocetine.
2003 May 20
[Neuroprotection strategies: effect of vinpocetine in vitro oxidative stress models].
2003 Nov-Dec
"Brain-specific" nutrients: a memory cure?
2003 Nov-Dec
[Memory and potassium channels].
2003 Oct-Dec
[Use of cavinton in neuropaediatrics].
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
Effects of various selective phosphodiesterase inhibitors on carbachol-induced contraction and cyclic nucleotide contents in guinea pig taenia coli.
2004 Sep
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
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
[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
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
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
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
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 Sat Dec 16 15:52:28 GMT 2023
Edited
by admin
on Sat Dec 16 15:52:28 GMT 2023
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
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
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
Classification Tree Code System Code
DSLD 724 (Number of products:364)
Created by admin on Sat Dec 16 15:52:29 GMT 2023 , Edited by admin on Sat Dec 16 15:52:29 GMT 2023
WHO-VATC QN06BX18
Created by admin on Sat Dec 16 15:52:29 GMT 2023 , Edited by admin on Sat Dec 16 15:52:29 GMT 2023
WHO-ATC N06BX18
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NCI_THESAURUS C932
Created by admin on Sat Dec 16 15:52:29 GMT 2023 , Edited by admin on Sat Dec 16 15:52:29 GMT 2023
Code System Code Type Description
PUBCHEM
443955
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PRIMARY
EVMPD
SUB00070MIG
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PRIMARY
DAILYMED
543512OBTC
Created by admin on Sat Dec 16 15:52:29 GMT 2023 , Edited by admin on Sat Dec 16 15:52:29 GMT 2023
PRIMARY
WIKIPEDIA
VINPOCETINE
Created by admin on Sat Dec 16 15:52:29 GMT 2023 , Edited by admin on Sat Dec 16 15:52:29 GMT 2023
PRIMARY
FDA UNII
543512OBTC
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PRIMARY
NSC
760093
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PRIMARY
IUPHAR
5285
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PRIMARY
MESH
C013983
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PRIMARY
INN
4046
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PRIMARY
EPA CompTox
DTXSID5023740
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PRIMARY
DRUG CENTRAL
2828
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PRIMARY
ECHA (EC/EINECS)
256-028-0
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PRIMARY
ChEMBL
CHEMBL71752
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PRIMARY
RS_ITEM_NUM
1714608
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PRIMARY
CAS
42971-09-5
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PRIMARY
DRUG BANK
DB12131
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PRIMARY
SMS_ID
100000079134
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PRIMARY
RXCUI
24506
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PRIMARY RxNorm
NCI_THESAURUS
C152887
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PRIMARY
MERCK INDEX
m11458
Created by admin on Sat Dec 16 15:52:29 GMT 2023 , Edited by admin on Sat Dec 16 15:52:29 GMT 2023
PRIMARY Merck Index
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