Tribenoside

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 414208020

| IUPAC_name = Ethyl 3,5,6-tri-O-benzyl-D-glucofuranoside (TBGF)

| image = Tribenoside.svg

| tradename =

| Drugs.com = {{drugs.com|international|tribenoside}}

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| bioavailability =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 10310-32-4

| ATC_prefix = C05

| ATC_suffix = AX05

| ATC_supplemental = {{ATC|C05|CX01}}

| PubChem = 196122

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = Z7N0Y673NU

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1446743

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 169970

| C=29 | H=34 | O=6

| synonyms = (3R,4R,5R)-4-(Benzyloxy)-5-[1,2-bis(benzyloxy)ethyl]-2-ethoxyoxolan-3-ol

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ULLNJSBQMBKOJH-VIVFLBMVSA-N

| smiles = CCOC1[C@@H]([C@H]([C@H](O1)[C@@H](COCc2ccccc2)OCc3ccccc3)OCc4ccccc4)O

}}

Tribenoside (Glyvenol) is a vasoprotective drug used to treat hemorrhoids.{{cite journal |author=Lorenc Z, Gökçe Ö |title=Tribenoside and lidocaine in the local treatment of hemorrhoids: an overview of clinical evidence. |journal=Eur Rev Med Pharmacol Sci |year=2016 |volume=20 |issue=12 |pages=2742–51 |pmid=27383331 |url=https://www.europeanreview.org/article/11037}} It has mild anti-inflammatory, analgesic, and wound healing properties.{{cite journal |author=Jaques R |title=The pharmacological activity of tribenoside. |journal=Pharmacology |year=1977 |volume=15 |issue=5 |pages=445–60 |pmid=578928 |doi=10.1159/000136721 |url=https://www.karger.com/Article/Abstract/136721}} Tribenoside stimulates laminin α5 production and laminin-332 deposition to help repair the basement membrane during the wound healing process.{{cite journal|author=Kikkawa Y, Takaki S, Matsuda Y, Okabe K, Taniguchi M, Oomachi K, Samejima T, Katagiri F, Hozumi K, Nomizu M |title=The influence of Tribenoside on expression and deposition of epidermal laminins in HaCaT cells. |journal=Biol Pharm Bull |year=2010 |volume=33 |issue=2 |pages=307–10 |pmid=20118558 |doi=10.1248/bpb.33.307 |url=https://www.jstage.jst.go.jp/article/bpb/33/2/33_2_307/_article|doi-access=free }} It is a mixture of the α- and β-anomers.{{cn|date=January 2020}}

Tribenoside has been shown to induce drug hypersensitivity syndrome in association with CMV reactivation.{{cite journal |vauthors=Hashizume H, Takigawa M |title=Drug-induced hypersensitivity syndrome associated with cytomegalovirus reactivation: immunological characterization of pathogenic T cells |journal=Acta Derm. Venereol. |volume=85 |issue=1 |pages=47–50 |year=2005 |pmid=15848991 |doi=10.1080/00015550410024094 |doi-access=free }}