Glibornuride

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Glibornuride
Glibornuride.svg
Names
IUPAC name
1-(3-hydroxy-4,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl)-3-(4-methylphenyl)sulfonylurea
Identifiers
3D model (Jmol)
ChemSpider
DrugBank
ECHA InfoCard 100.043.735
EC Number 248-124-6
KEGG
MeSH C073323
UNII
Properties
C18H26N2O4S
Molar mass 366.48 g/mol
Pharmacology
A10BB04 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Glibornuride (INN) is an anti-diabetic drug from the group of sulfonylureas.[1] It is manufactured by MEDA Pharma and sold in Switzerland under the brand name Glutril.[2]

Synthesis[edit]

Glibornuride synthesis:[3] See also: U.S. Patent 3,770,761; eidem, U.S. Patent 3,654,357 (to Hoffmann-La Roche).

Gliburnide is an endo-endo derivative made from camphor-3-carboxamode by borohydride reduction (exo approach), followed by Hofmann rearrangement to carbamate, followed by displacement with sodium tosylamide.

References[edit]

  1. ^ Haupt E, Köberich W, Beyer J, Schöffling K (December 1971). "Pharmacodynamic aspects of tolbutamide, glibenclamide, glibornuride and glisoxepide. I. Dose response relations and repeated administration in diabetic subjects". Diabetologia. 7 (6): 449–54. doi:10.1007/bf01212061. PMID 5004178. 
  2. ^ "Glutril — Drugs.com". Drugs.com. Retrieved 12 July 2016. 
  3. ^ Bretschneider, H.; Hohenlohe-Oehringen, K.; Graßmayr, K. (1969). "Arylsulfonylureido- und Arylsulfonylamidoacyl-derivate von Oxy- und Oxo-cycloalkanen als potentielle Antidiabetica". Monatshefte für Chemie. 100 (6): 2133. doi:10.1007/BF01151769.