Glibornuride

Glibornuride

Names
IUPAC name 1-(6-hydroxy-1,7,7-trimethyl-5-bicyclo[2.2.1]heptanyl)-3-(4-methylphenyl)sulfonylurea
Identifiers
CAS Number	26944-48-9 Y
ChemSpider	16735831 N
DrugBank	DB08962 N
EC Number	248-124-6
Jmol 3D model	Interactive image
KEGG	D02427 Y
MeSH	C073323
PubChem	33649
UNII	VP83E7434R Y
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 N Key: RMTYNAPTNBJHQI-LLDVTBCESA-N 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 mass	366.48 g/mol
Pharmacology
ATC code	A10BB04
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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

Synthesis

Glibornuride synthesis: 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.