4478. Glyburide

Nomenclature

CAS number: 10238-21-8
5-Chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxybenzamide; 1-[[p-[2-(5-chloro-o-anisamido)ethyl]phenyl]sulfonyl]-3-cyclohexylurea; N-[4-(β-(2-methoxy-5-chlorobenzamido)ethyl)benzosulfonyl]-N′-cyclohexylurea; N1-[4-[β-(2-methoxy-5-chlorobenzoylamino)ethyl]benzenesulfonyl]-N2-cyclohexylurea; glybenzcyclamide; glibenclamide; HB-419; U-26452; Azuglucon (Azupharma); Bastiverit (Bastian-Werk); Diabasan (Biofarma); Diabeta (Sanofi-Aventis); Daonil (Sanofi-Aventis); Duraglucon (Dura); Euglucon (Sanofi-Aventis); Gilemal (Chinoin); Glimidstada (Stada); Glycolande (Sanofi-Synthelabo); Libanil (APS); Maninil (Berlin-Chemie); Micronase (Pharmacia & Upjohn); Praeciglucon (Pfleger).
C23H28ClN3O5S; mol wt 494.00.
C 55.92%, H 5.71%, Cl 7.18%, N 8.51%, O 16.19%, S 6.49%.

Description and references

Second generation sulfonylurea with hypoglycemic activity. Prepn: Aumuller et al., Arzneim.-Forsch. 16, 1640 (1966); NL 6603398 (1966 to Boehringer, Mann.), C.A. 66, 65289h (1967); NL 6610580; H. Weber et al., US 3454635 (1967, 1969 both to Hoechst). Pharmacology: Loubatières, Mariani, C. R. Seances Acad. Sci. Ser. D 265, 643 (1967). Toxicity: Mizukami et al., Arzneim.-Forsch. 19, 1413 (1969). Series of articles on synthesis, pharmacology, toxicology and clinical studies: ibid. 1323-1494. Effect on release of insulin, glucagon and somatostatin: S. Efendic et al., Proc. Natl. Acad. Sci. USA 76, 5901 (1979). Symposium on pharmacology, mechanism of action and clinical trials: Ann. Clin. Res. 15, Suppl. 37, 1-35 (1983). Comprehensive description: P. G. Takla, Anal. Profiles Drug Subs. 10, 337-355 (1981). Review of pharmacology and clinical efficacy: J. M. Feldman, Pharmacotherapy 5, 43-62 (1985).

Chemical structure

Properties

Crystals from methanol, mp 169-170° (Weber); also reported as mp 172-174° (Aumüller). pKa 5.3. Sparingly sol in water, sol in the usual organic solvents. LD50 in rats and mice (g/kg): >20 orally; >12.5 i.p.; >20 s.c. (Mizukami).

Therapeutic Category

Antidiabetic.

Keywords

Antidiabetic; Sulfonylurea Derivatives