Glibornuride
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 444003955
| ImageFile = Glibornuride.svg
| ImageSize = 250
| IUPACName = N-{[(1R,2R,3S,4S)-2-Hydroxybornan-3-yl]carbamoyl}-4-methylbenzene-1-sulfonamide
| SystematicName = N-{[(1S,2S,3R,4R)-3-Hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]carbamoyl}-4-methylbenzene-1-sulfonamide
| OtherNames =
| Section1 = {{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = VP83E7434R
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=26944-48-9
| PubChem=33649
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB08962
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02427
| SMILES=CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC2C3CCC(C2O)(C3(C)C)C
| InChI = 1/C18H26N2O4S/c1-11-5-7-12(8-6-11)25(23,24)20-16(22)19-14-13-9-10-18(4,15(14)21)17(13,2)3/h5-8,13-15,21H,9-10H2,1-4H3,(H2,19,20,22)/t13-,14+,15+,18+/m1/s1
| InChIKey = RMTYNAPTNBJHQI-LLDVTBCEBZ
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C18H26N2O4S/c1-11-5-7-12(8-6-11)25(23,24)20-16(22)19-14-13-9-10-18(4,15(14)21)17(13,2)3/h5-8,13-15,21H,9-10H2,1-4H3,(H2,19,20,22)/t13-,14+,15+,18+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = RMTYNAPTNBJHQI-LLDVTBCESA-N
| RTECS =
| MeSHName = C073323
| EINECS = 248-124-6
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 16735831
}}
| Section2 = {{Chembox Properties
| Formula = C18H26N2O4S
| MolarMass = 366.48 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
| Section6 = {{Chembox Pharmacology
| ATCCode_prefix = A10
| ATCCode_suffix = BB04
}}
| Section7 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Glibornuride (INN) is an anti-diabetic drug from the group of sulfonylureas.{{cite journal |vauthors=Haupt E, Köberich W, Beyer J, Schöffling K |title=Pharmacodynamic aspects of tolbutamide, glibenclamide, glibornuride and glisoxepide. I. Dose response relations and repeated administration in diabetic subjects |journal=Diabetologia |volume=7 |issue=6 |pages=449–54 |date=December 1971 |pmid=5004178 |doi=10.1007/bf01212061|doi-access=free }} It is manufactured by MEDA Pharma and sold in Switzerland under the brand name Glutril.{{cite web|title=Glutril — Drugs.com|url=https://www.drugs.com/international/glutril.html|website=Drugs.com|access-date=12 July 2016|archive-date=14 September 2016|archive-url=https://web.archive.org/web/20160914204342/https://www.drugs.com/international/glutril.html|url-status=live}}
Synthesis
File:Glibornuride synthesis.svg
Gliburnide is an endo-endo derivative made from camphor-3-carboxamide by borohydride reduction (exo approach), followed by Hofmann rearrangement to carbamate, followed by displacement with sodium tosylamide.
References
{{Reflist}}
{{Oral hypoglycemics and insulin analogs}}
{{Ion channel modulators}}
Category:Potassium channel blockers
Category:1-(Benzenesulfonyl)-3-cyclohexylureas
{{gastrointestinal-drug-stub}}