Vinpocetine

Structural formula
General
Non-proprietary name	Vinpocetine
other names	Ethyl (+) - cis -apovincaminate; (3 α , 16 α ) -Eburnamenine-14-carboxylic acid ethyl ester; (15 S , 19 S ) -15-ethyl-1,11-diazapentacyclo [9.6.2.0 2.7 .0 8.18 .0 15.19 ] nonadeca-2,4,6,8 (18), 16- ethyl pentaene-17-carboxylate;
Molecular formula	C 22 H 26 N 2 O 2
Brief description	white to pale yellow, crystalline powder
External identifiers / databases
EC number	256-028-0
ECHA InfoCard	100.050.917
PubChem	443955
DrugBank	DB12131
Wikidata	Q420288
Drug information
ATC code	N06 BX18
properties
Molar mass	350.46 g · mol -1
Physical state	firmly
Melting point	149 to 152 ° C
solubility	practically insoluble in water; soluble in dichloromethane , methanol , chloroform and mineral acids; sparingly soluble in anhydrous ethanol ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	503 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Vinpocetine is a semi-synthetic derivative of (+) - vincamine , the main alkaloid of the little evergreen , and is used as a medicinal substance.

Pharmacological properties

Vinpocetine causes the blood vessels in the brain to expand in vivo (cerebral vasodilation ) and increases the cerebral catecholamine metabolism. It inhibits u. a. the phosphodiesterase type 1. The exact mechanism of action is not known.

Clinical information

application areas

Cerebrovascular disorders, dementia and mild to moderate psychosyndrome are indicated as areas of application . The effectiveness of vinpocetine for use in Alzheimer's disease has been debated.

Side effects

Side effects reported include headaches, sleep disorders, gastrointestinal disorders, drop in blood pressure and an increased heart rate ( tachycardia ).

Other Information

Medicines containing vincopocetin (Cavinton ^® ) have not been on the market in Germany since 2006, due to the expiry of the fictitious approval . Vinpocetine is monographed as a medicinal substance in the European Pharmacopoeia .

In addition to being a medicinal substance, vinpocetine is also used as a chiral reagent in stereoselective syntheses.

Individual evidence

↑ ^a ^b ^c ^d data sheet VINPOCETINE CRS (PDF) at EDQM , accessed on April 30, 2009.
↑ ^a ^b ^c ^d ^e ^f Commentary on the European Pharmacopoeia 6.0, loose-leaf collection, 30th edition 2008.
↑ ^a ^b data sheet Vinpocetine from Sigma-Aldrich , accessed on April 25, 2011 ( PDF ).
^ Medina AE, Krahe TE, Ramoa AS. Restoration of neuronal plasticity by a phosphodiesterase type 1 inhibitor in a model of fetal alcohol exposure. J Neurosci. 2006; 26 : 1057-1060. PMID 16421325 .
↑ European Pharmacopoeia, 6th edition, basic work 2008, 6.0 / 2139.

[Ph._Eur.-1] ta sheet VINPOCETINE CRS (PDF) at EDQM , accessed on April 30, 2009.

[pheurkom-2] ↑ ^a ^b ^c ^d ^e ^f Commentary on the European Pharmacopoeia 6.0, loose-leaf collection, 30th edition 2008.

[Sigma-3] ta sheet Vinpocetine from Sigma-Aldrich , accessed on April 25, 2011 ( PDF ).

[4] Medina AE, Krahe TE, Ramoa AS. Restoration of neuronal plasticity by a phosphodiesterase type 1 inhibitor in a model of fetal alcohol exposure. J Neurosci. 2006; 26 : 1057-1060. PMID 16421325 .

[EP0345-5] European Pharmacopoeia, 6th edition, basic work 2008, 6.0 / 2139.