CAS No 10238-21-8 , 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-
methoxybenzamide

Title: Glyburide
CAS Registry Number: 10238-21-8
CAS Name: 5-Chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxybenzamide
Synonyms: 1-[[p-[2-(5-chloro-o-anisamido)ethyl]phenyl]sulfonyl]-3-cyclohexylurea; N-[4-(b-(2-methoxy-5-chlorobenzamido)ethyl)benzosulfonyl]-N￠-cyclohexylurea; N1-[4-[b-(2-methoxy-5-chlorobenzoylamino)ethyl]benzenesulfonyl]-N2-cyclohexylurea; glybenzcyclamide; glibenclamide
Manufacturers' Codes: HB-419; U-26452
Trademarks: 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)
Molecular Formula: C23H28ClN3O5S
Molecular Weight: 494.00
Percent Composition: C 55.92%, H 5.71%, Cl 7.18%, N 8.51%, O 16.19%, S 6.49%
Literature 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).
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).
Melting point: mp 169-170° (Weber); mp 172-174° (Aumüller)
pKa: pKa 5.3
Toxicity data: LD50 in rats and mice (g/kg): >20 orally; >12.5 i.p.; >20 s.c. (Mizukami)
Therap-Cat: Antidiabetic.
Keywords: Antidiabetic; Sulfonylurea Derivatives.