4444. Glisoxepid

Nomenclature

CAS number: 25046-79-1
N-[2-[4-[[[[(Hexahydro-1H-azepin-1-yl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methyl-3-isoxazolecarboxamide; 1-(hexahydro-1H-azepin-1-yl)-3-[[p-[2-(5-methyl-3-isoxazolecarboxamido)ethyl]phenyl]sulfonyl]urea; 4-[4-[β-(5-methylisoxazole-3-carboxamido)ethyl]phenylsulfonyl]-1,1-hexamethylenesemicarbazide; BS-4231; RP-22410; Pro-Diaban (Bayer; Schering AG).
C20H27N5O5S; mol wt 449.52.
C 53.44%, H 6.05%, N 15.58%, O 17.80%, S 7.13%.

Description and references

Prepn: H. Plümpe, W. Puls, ZA 6806886; eidem, US 3668215 (1969, 1972 both to Bayer). Pharmacology: Loubatieres et al., C. R. Seances Acad. Sci. Ser. D 271, 1446 (1970); J. Pharmacol. 3, 171, 229 (1972). Toxicity study: Tettenborn, Arzneim.-Forsch. 24, 409 (1974). Series of articles: ibid. 363-452.

Chemical structure

Properties

Colorless crystals from ethanol, mp 189°. LD50 in mice, rats, cats, dogs (g/kg): >10.0, >10.0, >4.0, >2.0 orally; in mice, rats (mg/kg): 283, 196 i.v. (Tettenborn).

Therapeutic Category

Antidiabetic.

Keywords

Antidiabetic; Sulfonylurea Derivatives