| Identification | Back Directory | [Name]
Tribenoside | [CAS]
10310-32-4 | [Synonyms]
TBGF
Venex
Alven
Ba 21401
Flebosan
Glivenol
21401-Ba
Tohcuron
Glyvenal
Glyvenol
Hemocuron
TRIBENOSIDE
Tribenzoside
-1,2-bis(benzyloxy)
-2-ethoxytetrahydrofuran-3-ol
ETHYL-3,5,6-TRI-O-BENZYL-D-GLUCOFURANOSIDE
1-O-Ethyl-3-O,5-O,6-O-tribenzyl-D-glucofuranose
Glucofuranoside, ethyl 3,5,6-tri-O-benzyl- (7CI)
Glucofuranoside, ethyl 3,5,6-tri-O-benzyl-, D- (8CI)
D-Glucofuranoside,ethyl 3,5,6-tris-O-(phenylMethyl)-
D-Glucofuranoside, ethyl 3,5,6-tris-O-(phenylmethyl)- (9CI)
(3R,4R,5R)-5-[1,2-Bis(phenylmethoxy)ethyl]-2-ethoxy-4-(phenylmethoxy)oxolan-3-ol
(3R,4R,5R)-4-(Benzyloxy)-5-((R)-1,2-bis(benzyloxy)ethyl)-2-ethoxytetrahydrofuran-3-ol | [EINECS(EC#)]
233-687-2 | [Molecular Formula]
C29H34O6 | [MDL Number]
MFCD00801089 | [MOL File]
10310-32-4.mol | [Molecular Weight]
478.577 |
| Chemical Properties | Back Directory | [Appearance]
Yellowish to pale yellow, clear, viscous liquid. | [alpha ]
D26 +8° (chloroform) | [Boiling point ]
bp1.2 270-280° | [density ]
1.19±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Practically insoluble in water, very soluble in acetone, in methanol and in methylene chloride. | [form ]
neat | [pka]
13.01±0.70(Predicted) | [color ]
Pale Yellow to Light Yellow | [Contact allergens]
This drug is used for the treatment, both topical and
oral, of hemorrhoids. It leads to benzo?c acid, that is
contained in Myroxylon pereirae as well, and could be
the sensitizer. | [InChIKey]
ULLNJSBQMBKOJH-VIVFLBMVSA-N | [SMILES]
O(CC)C1O[C@H]([C@@H](COCC2=CC=CC=C2)OCC2=CC=CC=C2)[C@H](OCC2=CC=CC=C2)[C@H]1O | [Uses]
Sclerosing agent. | [CAS DataBase Reference]
10310-32-4 |
| Hazard Information | Back Directory | [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 | [storage]
-20°C | [References]
[1] S. Zga?arová. “Pathophysiological characterization of drug hypersensitivity to tribenoside.” Central European Journal of Medicine 9 1 (2014): 159–168.
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