Title: Florfenicol
CAS Registry Number: 73231-34-2
CAS Name: 2,2-Dichloro-N-[(1S,2R)-1-(fluoromethyl)-2-hydroxy-2-[4-(methylsulfonyl)phenyl]ethyl]acetamide
Additional Names: D-(threo)-1-p-methylsulfonylphenyl-2-amino-3-fluoro-1-propanol; fluorothiamphenicol
Manufacturers' Codes: Sch-25298
Trademarks: Aquafen (Schering-Plough); Aquaflor (Schering-Plough); Florocol (Schering-Plough); Nuflor (Schering-Plough)
Molecular Formula: C12H14Cl2FNO4S
Molecular Weight: 358.21
Percent Composition: C 40.24%, H 3.94%, Cl 19.79%, F 5.30%, N 3.91%, O 17.87%, S 8.95%
Literature References: Fluorinated derivative of thiamphenicol, q.v. Inhibits bacterial protein synthesis by binding to ribosome 50S and 70S subunits. Prepn: T. Nagabhushan, EP 14437; US 4235892 (both 1980 to Schering); D. P. Schumacher et al., J. Org. Chem. 55, 5291 (1990). Improved prepn: G. Wu et al., ibid. 62, 2996 (1997). HPLC determn in fish plasma: C. Vue et al., J. Chromatogr. B 780, 111 (2002). In vitro antibacterial activity: H. C. Neu, K. P. Fu, Antimicrob. Agents Chemother. 18, 311 (1980); V. P. Syriopoulou et al., ibid. 19, 294 (1981); vs bovine and porcine respiratory disease isolates: S. J. Shin et al., Vet. Microbiol. 106, 73 (2005). Pharmacokinetics in veal calves: K. J. Varma et al., J. Vet. Pharmacol. Ther. 9, 412 (1986); in sheep: J. Shen et al., ibid. 27, 163 (2004). Therapeutic effect on pseudotuberculosis in yellowtail tuna: N. Yasunaga, S. Yasumoto, Fish Pathol. 23, 1 (1988).
Properties: Crystals from 2-propanol/H2O, mp 152-154°. [a]26 +17.9° (DMF). Sol in water.
Melting point: mp 152-154°
Optical Rotation: [a]26 +17.9° (DMF)
Therap-Cat-Vet: Antibacterial. |