Glibornuride

Glibornuride

Names
IUPAC name N-{[(1R,2R,3S,4S)-2-Hydroxybornan-3-yl]carbamoyl}-4-methylbenzene-1-sulfonamide
Systematic IUPAC name N-{[(1S,2S,3R,4R)-3-Hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]carbamoyl}-4-methylbenzene-1-sulfonamide
Identifiers
CAS Number	26944-48-9  Y
3D model (JSmol)	Interactive image
ChemSpider	16735831  N
DrugBank	DB08962  N
ECHA InfoCard	100.043.735
EC Number	248-124-6
KEGG	D02427  Y
MeSH	C073323
PubChem CID	33649
UNII	VP83E7434R  Y
CompTox Dashboard (EPA)	DTXSID001016937
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 ( WHO )
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. ^[1] It is manufactured by MEDA Pharma and sold in Switzerland under the brand name Glutril. ^[2]

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

References

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. Archived from the original on 14 September 2016. 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.