Synonym
Alven; Ba 21401; Ethyl 3,5,6-tri-O-benzyl-D-glucofuranoside; Ethyl 3,5,6-tri-O-benzyl-D-glucofuranoside; Flebosan; Glivenol; Glyvenal; Glyvenol; Hemocuron; TBGF; Tribenoside; Tribenzoside; Venex;
IUPAC/Chemical Name
D-Glucofuranoside, ethyl 3,5,6-tris-O-(phenylmethyl)-
InChi Key
ULLNJSBQMBKOJH-VIVFLBMVSA-N
InChi Code
InChI=1S/C29H34O6/c1-2-32-29-26(30)28(34-20-24-16-10-5-11-17-24)27(35-29)25(33-19-23-14-8-4-9-15-23)21-31-18-22-12-6-3-7-13-22/h3-17,25-30H,2,18-21H2,1H3/t25-,26-,27-,28-,29?/m1/s1
SMILES Code
O[C@H]([C@H]([C@@H]([C@@H](COCC1=CC=CC=C1)OCC2=CC=CC=C2)O3)OCC4=CC=CC=C4)C3OCC
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
In vitro activity:
Tribenoside has been found to increase the migration rate of fibroblasts in vitro and to improve the wound healing process by promoting re-epithelialization in rats. Furthermore, novel antioxidant activity of tribenoside has been reported, which may represent a further mechanism of action in wound healing.
Reference:
Malinverno M, Callegari E, Pirona L, Pellerani I, Belmonte B, Tripodo C, Angelico P, Biondi S. Procto-Glyvenol© accelerates the natural healing process of wounds: a pre-clinical study. Eur Rev Med Pharmacol Sci. 2023 Sep;27(17):8269-8279. doi: 10.26355/eurrev_202309_33587. PMID: 37750654.
In vivo activity:
Procto-Glyvenol© improves the natural healing process of wounds by stimulating cell migration and protecting against the toxic effects of reactive oxygen species. Therefore, it may represent a first-line treatment for hemorrhoids, which are a significant medical and socioeconomic problem that can deteriorate the quality of life.
Reference:
Malinverno M, Callegari E, Pirona L, Pellerani I, Belmonte B, Tripodo C, Angelico P, Biondi S. Procto-Glyvenol© accelerates the natural healing process of wounds: a pre-clinical study. Eur Rev Med Pharmacol Sci. 2023 Sep;27(17):8269-8279. doi: 10.26355/eurrev_202309_33587. PMID: 37750654.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
478.59
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
In vitro protocol:
Malinverno M, Callegari E, Pirona L, Pellerani I, Belmonte B, Tripodo C, Angelico P, Biondi S. Procto-Glyvenol© accelerates the natural healing process of wounds: a pre-clinical study. Eur Rev Med Pharmacol Sci. 2023 Sep;27(17):8269-8279. doi: 10.26355/eurrev_202309_33587. PMID: 37750654.
Hashizume H, Takigawa M. Drug-induced hypersensitivity syndrome associated with cytomegalovirus reactivation: immunological characterization of pathogenic T cells. Acta Derm Venereol. 2005;85(1):47-50. doi: 10.1080/00015550410024094. PMID: 15848991.
In vivo protocol:
Malinverno M, Callegari E, Pirona L, Pellerani I, Belmonte B, Tripodo C, Angelico P, Biondi S. Procto-Glyvenol© accelerates the natural healing process of wounds: a pre-clinical study. Eur Rev Med Pharmacol Sci. 2023 Sep;27(17):8269-8279. doi: 10.26355/eurrev_202309_33587. PMID: 37750654.
1: Kikkawa Y, Takaki S, Matsuda Y, Okabe K, Taniguchi M, Oomachi K, Samejima T, Katagiri F, Hozumi K, Nomizu M. The influence of Tribenoside on expression and deposition of epidermal laminins in HaCaT cells. Biol Pharm Bull. 2010;33(2):307-10. PubMed PMID: 20118558.
2: Lorenc Z, Gökçe Ö. Tribenoside and lidocaine in the local treatment of hemorrhoids: an overview of clinical evidence. Eur Rev Med Pharmacol Sci. 2016 Jun;20(12):2742-51. Review. PubMed PMID: 27383331.
3: Kalbhen DA, Felten K. Effects of tribenoside (Glyvenol) on experimental osteoarthrosis. Pharmacology. 1979;19(2):68-74. PubMed PMID: 583363.
4: Kalbhen DA, Scherbach E, Felten K. [Histology of the antiarthritic effect of tribenoside in experimental gonarthrosis]. Z Rheumatol. 1981 Mar-Apr;40(2):72-86. German. PubMed PMID: 6895141.
5: Sioufi A, Pommier F. Biotransformation of tribenoside into benzoic acid in man. Eur J Drug Metab Pharmacokinet. 1982;7(3):223-8. PubMed PMID: 6897385.
6: Kalbhen DA, Scherbach E, Felten K. Histological investigations of the antiarthrotic effect of tribenoside (Glyvenol) in experimental osteoarthrosis. J Rheumatol. 1983 Apr;10(2):267-81. PubMed PMID: 6345770.
7: Endo H, Kawada A, Yudate T, Aragane Y, Yamada H, Tezuka T. Drug eruption due to tribenoside. Contact Dermatitis. 1999 Oct;41(4):223. PubMed PMID: 10515105.
8: Plenis A, Konieczna L, Miękus N, Bączek T. Development of the HPLC Method for Simultaneous Determination of Lidocaine Hydrochloride and Tribenoside Along with Their Impurities Supported by the QSRR Approach. Chromatographia. 2013 Mar;76(5-6):255-265. Epub 2012 Nov 1. PubMed PMID: 23482886; PubMed Central PMCID: PMC3585984.
9: Kubicsek T, Kazy Z, Czeizel AE. Teratogenic potential of tribenoside, a drug for the treatment of haemorrhoids and varicose veins--a population-based case--control study. Reprod Toxicol. 2011 May;31(4):464-9. doi: 10.1016/j.reprotox.2010.12.001. Epub 2010 Dec 21. PubMed PMID: 21182931.
10: Inoue A, Tamagawa-Mineoka R, Katoh N, Kishimoto S. Allergic contact dermatitis caused by tribenoside. Contact Dermatitis. 2009 Jun;60(6):349-50. doi: 10.1111/j.1600-0536.2009.01544.x. PubMed PMID: 19489977.
11: Spinella G, Majorana M. [Tribenoside in the treatment of varicose disease of the lower limbs: controlled clinical study]. Clin Ter. 1982 Jun 30;101(6):587-601. Italian. PubMed PMID: 6751664.
12: Muschietti B. [Clinical double blind trial with natural diosmin, synthetic diosmin and tribenoside (author's transl)]. Schweiz Rundsch Med Prax. 1978 Sep 26;67(39):1449-52. French. PubMed PMID: 362404.
13: Wilhelmi G. Regeneration-promoting properties of tribenoside in Amblystoma mexicanum. Pharmacology. 1976;14(5):397-404. PubMed PMID: 1037626.
14: Majer H. Stabilization of rat erythrocytes against the haemolytic effect of glass particles by tribenoside. Agents Actions. 1975 May;5(2):161-3. PubMed PMID: 1174008.
15: Jaques R, Keberle H, Riesterer L, Schmid K. On the percutaneous absorption of tribenoside applied topically to the mouse ear. Experientia. 1969 Oct 15;25(10):1023-4. PubMed PMID: 4243405.
16: Jaques R. The pharmacological activity of tribenoside. Pharmacology. 1977;15(5):445-60. PubMed PMID: 578928.
17: Rüegg M, Jaques R. Tribenoside as an inhibitor of chemically induced histamine release. Experientia. 1974 Apr 15;30(4):399-401. PubMed PMID: 4135153.
18: Wilhelmi G. [Preventive effect of tribenoside in spontaneous arthrosis of the mouse]. Z Rheumatol. 1977 Mar-Apr;36(3-4):112-9. German. PubMed PMID: 577067.
19: Wilhelmi G, Faust R. Suitability of the C57 black mouse as an experimental animal for the study of skeletal changes due to ageing, with special reference to osteo-arthrosis and its response to tribenoside. Pharmacology. 1976;14(4):289-96. PubMed PMID: 947093.
20: Wilhelmi G. [Effect of orally administered tribenoside on wound healing in the normal rat skin]. Arzneimittelforschung. 1974 Jun;24(6):934-7. German. PubMed PMID: 4408053.
