4440. Glimepiride

Nomenclature

CAS number: 93479-97-1
3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(trans-4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1-carboxamide; N-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-ethyl]-benzenesulfonyl]-N′-4-methylcyclohexylurea; 1-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl]phenylsulfonyl]-3-(4-methylcyclohexyl)urea; HOE-490; Amarel (Sanofi-Aventis); Amaryl (Sanofi-Aventis); Solosa (Guidotti).
C24H34N4O5S; mol wt 490.62.
C 58.75%, H 6.99%, N 11.42%, O 16.31%, S 6.54%.

Description and references

Oral sulfonylurea; promotes insulin release at ATP-sensitive potassium channels on pancreatic β-cells via binding to a 65 kDa subunit of the sulfonylurea receptor. Prepn: R. Weyer et al., DE 2951135; eidem, US 4379785 (1981, 1983 both to Hoechst). Synthesis: R. Weyer, V. Hitzel, Arzneim.-Forsch. 38, 1079 (1988). Pharmacology: K. Geisen, ibid. 1120. Effects on insulin and glucagon secretion: V. Leclercq-Meyer et al., Biochem. Pharmacol. 42, 1634 (1991). HPLC determn in plasma: Y.-K. Song et al., J. Chromatogr. B 810, 143 (2004). Clinical pharmacokinetics: K. Ratheiser et al., Arzneim.-Forsch. 43, 856 (1993). Toxicity study: U. Schollmeier et al., ibid. 1038. Series of articles on pharmacology and clinical efficacy: Diabetes Res. Clin. Pract. 28 Suppl., S115-S149 (1995). Review of pharmacology and clinical use in type 2 diabetes: H. D. Langtry, J. A. Balfour, Drugs 55, 563-584 (1998); A. L. McCall, Expert Opin. Pharmacother. 2, 699-713 (2001).

Chemical structure

Properties

White to yellowish-white crystalline powder. mp 207°. Practically insol in water. Sol in DMSO; slightly sol in acetone; very slightly sol in acetonitrile, methanol.

Therapeutic Category

Antidiabetic.

Therapeutic Category (Veterinary)

Antidiabetic.

Keywords

Antidiabetic; Sulfonylurea Derivatives