Fluorinated analog of thiamphenicol with broad-spectrum, primarily bacteriostatic activity
REVIEW Florfenicol (Nuflor, Schering-Plough Animal Health) is an antibacterial that is a fluorinated synthetic analog of thiamphenicol and is very potent inhibitor of bacterial protein biosynthesis. In the United States, florfenicol is currently indicated for the treatment of bovine respiratory disease (BRD) associated with Mannheimia (Pasteurella) haemolytica, Pasteurella multocida, and Haemophilus somnus; and for treatment of bovine interdigital phlegmon (foot rot, acute interdigital necrobacillosis, infectious pododermatitis) associated with Fusobacterium necrophorum and Bacteroides melaninogenicus. Florfenicol is a bacteriostatic antibiotic that inhibits protein synthesis by binding to ribosomal subunits of susceptible bacteria, leading to the inhibition of peptidyl transferase and thereby preventing the transfer of amino acids to growing peptide chains and subsequent protein formation. The bacterial receptor that is the site of action for florfenicol is considered to be the same as that for chloramphenicol and thiamphenicol.
REFERENCES
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Nagabhushan, Tattanahalli Lakshminarayan 1-Aryl-2-acylamido-3-fluoro-1-propanols and pharmaceutical compositions containing them Eur. Pat. Appl. (1980), EP 14437 A2 19800820.
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Nagabhushan, Tattanahalli L. D-threo-1-Aryl-2-acylamido-3-fluoro-1-propanol esters and salts and their use as antibacterial agents U.S. (1982), US 4311857 A 19820119.Nagabhushan, Tattanahalli L ,D-threo-1-Aryl-2-acylamido-3-fluoro-1-propanol esters and salts and their use as antibacterial agents U.S. (1982), US 4311857 A 19820119.
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Jommi, Giancarlo; Pagliarin, Roberto; Chiarino, Dario; Fantucci, Mario Preparation of 2-[4-(methylsulfonyl)phenyl]-2,3-dihydrooxazolo[2,3-a]isoindol-5(9bH)-one derivatives and a new synthesis of thiamphenicol analogs Gazzetta Chimica Italiana (1985), 115(12, Pt. B), 653-8.@Dowling, Patricia M. Chloramphenicol, thiamphenicol, and florfenicol Edited by Giguere, Steeve Antimicrobial Therapy in Veterinary Medicine (4th Edition) (2006), 241-248.@Jommi, Giancarlo; Pagliarin, Roberto; Tavecchia, Paolo; Chiarino, Dario; Fantucci, Mario 2-Oxazolidinones as regioselective protection of beta-amino alcohols in the synthesis of 2-amino-1-aryl-3-fluoro-1-propanols Gazzetta Chimica Italiana (1986), 116(9), 485-9.@Schumacher, Doris P.; Clark, Jon E.; Murphy, Bruce L.; Fischer, Peter A. An efficient synthesis of florfenicol Journal of Organic Chemistry (1990), 55(18), 5291-4.@Syriopoulou VP, Harding AL, Goldmann DA, Smith AL. In vitro antibacterial activity of fluorinated analogs of chloramphenicol and thiamphenicol Antimicrob Agents Chemother. 1981 Feb;19(2):294-7.@Schwarz S, Kehrenberg C, Doublet B, Cloeckaert A.Molecular basis of bacterial resistance to chloramphenicol and florfenicol. FEMS Microbiol Rev. 2004 Nov;28(5):519-42.
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