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Linezolid

Linezolid is an oxazolidinone antibiotic that exhibits antibacterial activity against gram positive bacteria. Linezolid binds to the A site of 23S rRNA on the 50S ribosomal subunit, inhibiting protein synthesis. Linezolid also decreases NMDA receptor-mediated current, but is less active than most other comparable antibacterial compounds.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18940482

Cas No.

165800-03-3

Purity

≥98%

Formula

C16H20FN3O4

Formula Wt.

337.35

IUPAC Name

N-[[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide

Synonym

N-[[(5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Melting Point

178-182C

Solubility

Moderately soluble in water (3 mg/mL). Soluble in DMSO (>20 mg/mL).

Appearance

White to off white powder

Long KS, Vester B. Resistance to linezolid caused by modifications at its binding site on the ribosome. Antimicrob Agents Chemother. 2012 Feb;56(2):603-12. PMID: 22143525.

Kombian SB, Phillips OA. In vitro electrophysiological investigations of the acute effects of linezolid and novel oxazolidinones on central nervous system neurons. Neuroscience. 2011 Apr 28;180:53-63. PMID: 21296129.

Ippolito JA, Kanyo ZF, Wang D, et al. Crystal structure of the oxazolidinone antibiotic linezolid bound to the 50S ribosomal subunit. J Med Chem. 2008 Jun 26;51(12):3353-6. PMID: 18494460.

Brickner SJ, Hutchinson DK, Barbachyn MR, et.al. Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant gram-positive bacterial infections. J Med Chem. 1996 Feb 2;39(3):673-9. PMID: 8576909 DOI: 10.1021/jm9509556

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