Glibornuride

 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]

Glibornuride
Glibornuride.svg
Names
IUPAC name
1-(3-hydroxy-4,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl)-3-(4-methylphenyl)sulfonylurea
Identifiers
CAS Number
  • 26944-48-9 check
3D model (JSmol)
  • Interactive image
ChemSpider
  • 16735831 ☒
DrugBank
  • DB08962 ☒
ECHA InfoCard100.043.735 Edit this at Wikidata
EC Number
  • 248-124-6
KEGG
  • D02427 check
MeSHC073323
PubChem CID
  • 33649
UNII
  • VP83E7434R check
InChI
  • InChI=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 ☒
    Key: RMTYNAPTNBJHQI-LLDVTBCESA-N ☒
  • 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
    Key: RMTYNAPTNBJHQI-LLDVTBCEBZ
SMILES
  • CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC2C3CCC(C2O)(C3(C)C)C
Properties
Chemical formula
C18H26N2O4S
Molar mass366.48 g/mol
Pharmacology
ATC code
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

SynthesisEdit

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-carboxamide by borohydride reduction (exo approach), followed by Hofmann rearrangement to carbamate, followed by displacement with sodium tosylamide.

This article uses material from the Wikipedia article
 Metasyntactic variable, which is released under the 
Creative Commons
Attribution-ShareAlike 3.0 Unported License.