Vincamine

Structural formula
General
Non-proprietary name	Vincamine
other names	Vincamic acid methyl ester; (+) - vincamine; (+) - cis -incamine; (4 1 S , 12 S , 13a S ) -13a-ethyl-12-hydroxy-2,3,4 1 , 5,6,12,13,13a-octahydro-1 H -indolo [3,2,1- de ] pyrido [3,2,1- ij ] [1,5] naphthyridine-12-carboxylic acid methyl ester;
Molecular formula	C 21 H 26 N 2 O 3
Brief description	yellow crystals
External identifiers / databases
EC number	216-576-3
ECHA InfoCard	100.015.070
PubChem	15376
ChemSpider	14635
DrugBank	DB13374
Wikidata	Q416225
Drug information
ATC code	C04 AX07
Drug class	Peripheral vasodilator
properties
Molar mass	354.44 g · mol -1
Physical state	firmly
Melting point	232 ° C
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	1200 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 .

Vincamine is a compound from the natural group of alkaloids . It is used as a medicinal substance and can also be produced synthetically.

Occurrence

Little evergreen

With a share of 25 to 65% of the total alkaloid content, vincamine is the main alkaloid of the small periwinkle .

Analytics

For secure qualitative and quantitative determination of the vincamine come after adequate sample preparation chromatographic methods such. B. thin layer chromatography , HPLC and gas chromatography , also in combination with mass spectrometry . The analytical methods mentioned are also used in studies of the metabolism of vincamine.

Pharmacological properties

Vincamine is said to have a beneficial effect on the brain metabolism by improving the blood flow in the brain and increasing oxygen uptake and glucose supply.

Vincamine penetrates the blood-brain barrier and has a strong tendency to bind to the brain tissue proteins. The binding to plasma proteins is 30%. The elimination half- life is approximately 6 hours.

Clinical information

application areas

Vincamine is used for cerebral circulatory disorders and brain performance disorders (slight age-related impaired brain performance), circulatory disorders in the eye and inner ear, and Menière's disease . A therapeutic benefit for brain disorders is considered insufficiently proven.

Side effects

Side effects reported include gastrointestinal disorders, drop in blood pressure, cardiac arrhythmias , restlessness and dry mouth.

Other Information

Finished medicinal products containing vincamine ( pervincamine retard and others) have not been on the market in Germany since 2005, due to the expiry of the fictitious approval . In Switzerland, Vivamin was on the market as Oxygeron .

Vincamine is a monoterpene - indole alkaloid from Eburnamin type. Along with vincristine , vinblastine and vindoline, it belongs to the vinca alkaloids .

Vincamine is the starting material for the synthesis of Vinpocetine .

Individual evidence

↑ ^a ^b ^c T. Dingermann, K. Hiller, G. Schneider, I. Zündorf: Schneider drug drugs. 5th edition. Elsevier, 2004, ISBN 3-8274-1481-4 .
↑ ^a ^b ^c ^d Datasheet Vincamine from Sigma-Aldrich , accessed on April 25, 2011 ( PDF ).
↑ R. Na, L. Jiajia, Y. Dongliang, P. Yingzi, H. Juan, L. Xiong, Z. Nana, Z. Jing, L. Yitian: Indentification of vincamine indole alkaloids producing endophytic fungi isolated from Nerium indicum, Apocynaceae. In: Microbiol Res. 192, Nov 2016, pp. 114-121, Review. PMID 27664729 .
↑ A. Akhgari, I. Laakso, T. Seppänen-Laakso, T. Yrjönen, H. Vuorela, KM Oksman-Caldentey, H. Rischer: Determination of terpenoid indole alkaloids in hairy roots of Rhazya stricta (Apocynaceae) by GC-MS . In: Phytochem Anal. 26 (5), Sep-Oct 2015, pp. 331–338. PMID 26095837 .
↑ V. Viganò, p Paracchini, G. Piacenza, E. Pesce: Metabolism of Vincamine in the rat. In: Farmaco Sci. 33 (8), Aug 1978, pp. 583-594. Italian. PMID 744256 .
↑ technical information Oxygeron (Drossapharm), as of May of 2006.

[schneider-1] T. Dingermann, K. Hiller, G. Schneider, I. Zündorf: Schneider drug drugs. 5th edition. Elsevier, 2004, ISBN 3-8274-1481-4 .

[sigaldr-2] Datasheet Vincamine from Sigma-Aldrich , accessed on April 25, 2011 ( PDF ).

[3] R. Na, L. Jiajia, Y. Dongliang, P. Yingzi, H. Juan, L. Xiong, Z. Nana, Z. Jing, L. Yitian: Indentification of vincamine indole alkaloids producing endophytic fungi isolated from Nerium indicum, Apocynaceae. In: Microbiol Res. 192, Nov 2016, pp. 114-121, Review. PMID 27664729 .

[4] A. Akhgari, I. Laakso, T. Seppänen-Laakso, T. Yrjönen, H. Vuorela, KM Oksman-Caldentey, H. Rischer: Determination of terpenoid indole alkaloids in hairy roots of Rhazya stricta (Apocynaceae) by GC-MS . In: Phytochem Anal. 26 (5), Sep-Oct 2015, pp. 331–338. PMID 26095837 .

[5] V. Viganò, p Paracchini, G. Piacenza, E. Pesce: Metabolism of Vincamine in the rat. In: Farmaco Sci. 33 (8), Aug 1978, pp. 583-594. Italian. PMID 744256 .

[fi-6] technical information Oxygeron (Drossapharm), as of May of 2006.