Vinburnine

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Structural formula
Structure of vinburine
Structural formula of the (all- S ) - (-) - isomer
General
Non-proprietary name Vinburnine
other names
  • L -Eburnamonine
  • (all- S ) -13a-ethyl-2,3,4a1,5,6,13a-hexahydro-1 H -indolo [3,2,1- de ] pyrido [3,2,1- de ] - [1 , 5] naphthyridin-12-one
  • (-) - Vincamon
  • Vincamon
  • (-) - Eburnamonine
  • (-) - cis -Eburnamonine
Molecular formula C 19 H 22 N 2 O
External identifiers / databases
CAS number 4880-88-0
EC number 225-490-5
ECHA InfoCard 100.023.172
PubChem 71203
Wikidata Q2526386
Drug information
ATC code

C04 AX17

Drug class

peripheral vasodilator

properties
Molar mass 294.39 g · mol -1
Physical state

firmly

Melting point

168-170 ° C and 177-178 ° C ° C, respectively

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
08 - Dangerous to health

Caution

H and P phrases H: 373
P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Vinburnine (also L -Eburnamonine or (-) - Eburnamonine ) is a substance from the group of vinca alkaloids .

Small periwinkle ( Vinca minor )

It is formed by acid hydrolysis from vincamine , the main alkaloid of the small periwinkle ( Vinca minor ). The enantiomer (+) - eburnamonine occurs genuinely in Hunteria eburnea , also a plant from the dog venom family , the racemic form (±) -eburnamonine in Vinca minor .

Vinburnine belongs to the group of peripheral vasodilator substances and is said to have a positive effect on cerebral blood flow and metabolism. Accordingly, vinburnine is part of drugs for the treatment of cerebral circulatory disorders and brain disorders, such as B. mild age-related brain impairment [trade name: Cervoxan ( F , E )]. In Germany, Austria and Switzerland the substance is not used as a medicinal substance. Such finished medicinal products have since been withdrawn from the market in several other European countries.

Individual evidence

  1. a b The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 13th edition, 2006, p. 615.
  2. Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of (3α, 16α) -eburnamenin-14 (15H) -one in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 12, 2020, is reproduced from a self-classification by the distributor .
  3. Manfred Hesse: Alkaloids: Curse or Blessing of Nature? , P. 196. Helvetica Chimica Acta, 2000, ISBN 3-906390-19-5 .
  4. ^ ABDA database, accessed in May 2009.