9119. Telithromycin

Nomenclature

CAS number: 191114-48-4
3-De[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-l-ribohexopyranosyl)oxy]-11,12-dideoxy-6-O-methyl-3-oxo-12,11-[oxycarbonyl[[4-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl]imino]]erythromycin; HMR-3647; RU-66647; Ketek (Aventis).
C43H65N5O10; mol wt 812.00.
C 63.60%, H 8.07%, N 8.62%, O 19.70%.

Description and references

Semisynthetic macrolide antibiotic of the ketolide class, a group of erythromycin derivatives in which the l-cladinose residue has been replaced by a 3-keto group. Prepn: C. Agouridas et al., EP 680967; eidem, US 5635485 (1995, 1997 both to Roussel Uclaf); A. Denis et al., Bioorg. Med. Chem. Lett. 9, 3075 (1999). In vitro activity vs anaerobic bacteria: L. M. Ednie et al., Antimicrob. Agents Chemother. 41, 2019 (1997); vs gram-positive bacteria: K. Malathum et al., ibid. 43, 930 (1999). Time-kill kinetics: F. J. Boswell et al., J. Antimicrob. Chemother. 41, 149 (1998). HPLC analysis: B. Lingerfelt, W. S. Champney, J. Pharm. Biomed. Anal. 20, 459 (1999). Review of pharmacology and clinical trials: G. Ackermann, A. C. Rodloff, J. Antimicrob. Chemother. 51, 497-511 (2003).

Chemical structure

Properties

Crystals from ether, mp 187-188°.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); Macrolides