Tribenoside

Tribenoside (Glyvenol) is a vasoprotective drug used to treat hemorrhoids.[1] It has mild anti-inflammatory, analgesic, and wound healing properties.[2] Tribenoside stimulates laminin α5 production and laminin-332 deposition to help repair the basement membrane during the wound healing process.[3] It is a mixture of the α- and β-anomers.

Tribenoside
Clinical data
Other names(3R,4R,5R)-4-(Benzyloxy)-5-[1,2-bis(benzyloxy)ethyl]-2-ethoxyoxolan-3-ol
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • Ethyl 3,5,6-tri-O-benzyl-D-glucofuranoside (TBGF)
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.030.612
Chemical and physical data
FormulaC29H34O6
Molar mass478.585 g·mol−1
3D model (JSmol)
SMILES
  • CCOC1[C@@H]([C@H]([C@H](O1)[C@@H](COCc2ccccc2)OCc3ccccc3)OCc4ccccc4)O
InChI
  • 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 N
  • Key:ULLNJSBQMBKOJH-VIVFLBMVSA-N N
 NY (what is this?)  (verify)

Tribenoside has been shown to induce drug hypersensitivity syndrome in association with CMV reactivation.[4]

References
  1. Lorenc Z, Gökçe Ö (2016). "Tribenoside and lidocaine in the local treatment of hemorrhoids: an overview of clinical evidence". Eur Rev Med Pharmacol Sci. 20 (12): 2742–51. PMID 27383331.
  2. Jaques R (1977). "The pharmacological activity of tribenoside". Pharmacology. 15 (5): 445–60. doi:10.1159/000136721. PMID 578928.
  3. Kikkawa Y, Takaki S, Matsuda Y, Okabe K, Taniguchi M, Oomachi K, Samejima T, Katagiri F, Hozumi K, Nomizu M (2010). "The influence of Tribenoside on expression and deposition of epidermal laminins in HaCaT cells". Biol Pharm Bull. 33 (2): 307–10. doi:10.1248/bpb.33.307. PMID 20118558.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. Hashizume H, Takigawa M (2005). "Drug-induced hypersensitivity syndrome associated with cytomegalovirus reactivation: immunological characterization of pathogenic T cells". Acta Derm. Venereol. 85 (1): 47–50. doi:10.1080/00015550410024094. PMID 15848991.


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