Glibornuride

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Glibornuride
Glibornuride.png
Names
IUPAC name
1-(6-hydroxy-1,7,7-trimethyl-5-bicyclo[2.2.1]heptanyl)-3-(4-methylphenyl)sulfonylurea
Identifiers
26944-48-9 YesY
DrugBank DB08962 N
Jmol interactive 3D Image
KEGG D02427 YesY
PubChem 33649
UNII VP83E7434R YesY
Properties
C18H26N2O4S
Molar mass 366.48 g/mol
Pharmacology
ATC code A10BB04
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Glibornuride (INN) is an anti-diabetic drug from the group of sulfonylureas.[1]

Synthesis[edit]

Glibornuride synthesis:[2] 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. ^ 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.