4439. Gliclazide

Nomenclature

CAS number: 21187-98-4
N-[[(Hexahydrocyclopenta[c]pyrrol-2(1H)-yl)amino]carbonyl]-4-methylbenzenesulfonamide; 1-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-(p-tolylsulfonyl)urea; N-(4-methylbenzenesulfonyl)-N′-(3-azabicyclo[3.3.0]oct-3-yl)urea; 1-(3-azabicyclo[3.3.0]oct-3-yl)-3-(p-tolylsulfonyl)urea; S-1702; Diamicron (Servier); Glimicron (Dainippon); Nordialex (Pharmacodex).
C15H21N3O3S; mol wt 323.41.
C 55.71%, H 6.54%, N 12.99%, O 14.84%, S 9.91%.

Description and references

Prepn: Beregi et al., FR 1510714 and US 3501495 (1968 and 1970, both to Sci. Union & Co.-Soc. Franc. Rech. Med.). Series of articles on pharmacology: Arzneim.-Forsch. 22, 1686-1695 (1972). Toxicity data: J. Duhault et al., ibid. 1682. Review of pharmacology, efficacy: B. Holmes et al., Drugs 27, 301 (1984).

Chemical structure

Properties

Crystals from anhydrous ethanol, mp 180-182°. LD50 orally in mice: >3 g/kg (Duhault).

Therapeutic Category

Antidiabetic.

Keywords

Antidiabetic; Sulfonylurea Derivatives