Structural Formula Vector Image
Title: Linezolid
CAS Registry Number: 165800-03-3
CAS Name: N-[[(5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
Manufacturers' Codes: PNU-100766; U-100766
Trademarks: Zyvox (Pharmacia & Upjohn); Zyvoxid (Pharmacia & Upjohn)
Molecular Formula: C16H20FN3O4
Molecular Weight: 337.35
Percent Composition: C 56.96%, H 5.98%, F 5.63%, N 12.46%, O 18.97%
Literature References: Prototype of the oxazolidinone antimicrobials; inhibits bacterial mRNA translation. Prepn: M. R. Barbachyn et al., WO 9507271 (1995 to Upjohn); eidem, US 5688792 (1997 to Pharmacia & Upjohn); S. J. Brickner et al., J. Med. Chem. 39, 673 (1996). Antibacterial spectrum: C. W. Ford et al., Antimicrob. Agents Chemother. 40, 1508 (1996). Mechanism of action study: D. L. Shinabarger et al., ibid. 41, 2132 (1997). HPLC determn in plasma: C. Buerger et al., J. Chromatogr. B 796, 155 (2003). Clinical comparison with vancomycin, q.v., for MRSA infections: D. L. Stevens et al., Clin. Infect. Dis. 34, 1481 (2002). Review of pharmacology: L. D. Dresser, M. J. Rybak, Pharmacotherapy 18, 456-462 (1998); and clinical experience: R. Norrby, Expert Opin. Pharmacother. 2, 293-302 (2001).
Properties: White crystals from ethyl acetate and hexanes, mp 181.5-182.5°. [a]D20 -9° (c = 0.919 in chloroform).
Melting point: mp 181.5-182.5°
Optical Rotation: [a]D20 -9° (c = 0.919 in chloroform)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Synthetic); Oxazolidinones.

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