Hazard
Low toxicity by ingestion.
Description
Tribenoside is the semisynthetic sugar derivate ethyl-3, 5, 6-tri-O-benzyl-D-glucofuranoside, glucose with one ethyl and three benzyl groups. It is widely used in capsule (cps) form for oral administration and cream or suppositories for topical application under several brand names. Tribenoside is indicated for the treatment of chronic venous insufficiency, hemorrhoids, and arthritis. It has a high affinity for the vessel wall and a wide spectrum of pharmacological effects, including venotonic, anti-edematous, fibrinolysis-promoting, analgesic, anti-inflammatory (inhibiting histamine and prostaglandins), anti-allergic, membrane-stabilizing, and bactericidal effects. It regulates the expression and localization of laminins in epidermal cells to reconstruct basement membranes in wound healing[1].
Chemical Properties
Yellowish to pale yellow, clear, viscous liquid.
Originator
Glyvenol,Ciba,W. Germany,1967
Definition
ChEBI: (3R,4R,5R)-5-[(1R)-1,2-bis(phenylmethoxy)ethyl]-2-ethoxy-4-phenylmethoxy-3-oxolanol is a glycoside.
Manufacturing Process
4.9 g of 3,5,6-tribenzyl-1,2-isopropylidene glucofuranose are kept overnight at
room temperature with 100 cc of N-ethanolic hydrochloric acid. Evaporation
under vacuum at below 50°C is then carried out and the residue taken up in
150 cc of chloroform. The chloroform solution is thoroughly washed with
sodium bicarbonate solution, dried with calcined sodium sulfate and
evaporated under vacuum. The oily residue is then distilled under vacuum
with a free flame. In this manner there is obtained the ethyl-3,5,6-tribenzyl_x0002_D-glucofuranoside of boiling point 270°C to 275°C under 1 mm pressure.
The glucofuranose used as starting material is obtained as follows: 8.8 g of
1,2-isopropylidene-D-glucofuranose and 50.6 g of benzyl chloride are treated
with a total of 28 g of potassium hydroxide in portions with cooling and
stirring. The mixture is then stirred for 3 hours at 80°C to 90°C. Working up
from chloroform solution and distillation at 250°C to 260°C under 0.1 mm
pressure give 8.9 g of 1,2-isopropylidene-3,5,6-tribenzyl-D-glucofuranose.
Therapeutic Function
Topical venotonic
References
[1] S. Zga?arová. “Pathophysiological characterization of drug hypersensitivity to tribenoside.” Central European Journal of Medicine 9 1 (2014): 159–168.
