Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C12H14Cl2FNO4S |
Molecular Weight | 358.213 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(=O)(=O)C1=CC=C(C=C1)[C@@H](O)[C@@H](CF)NC(=O)C(Cl)Cl
InChI
InChIKey=AYIRNRDRBQJXIF-NXEZZACHSA-N
InChI=1S/C12H14Cl2FNO4S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-15)16-12(18)11(13)14/h2-5,9-11,17H,6H2,1H3,(H,16,18)/t9-,10-/m1/s1
Florfenicol (Nuflor) is a fluorinated synthetic analog of thiamphenicol. Florfenicol is indicated for the treatment of bovine respiratory disease (BRD) associated with Mannheimia (Pasteurella) haemolytica, Pasteurella multocida, and Haemophilus somnus, for treatment of bovine interdigital phlegmon (foot rot, acute interdigital necrobacillosis, infectious pododermatitis) associated with Fusobacterium necrophorum and Bacteroides melaninogenicus. Florfenicol is a broad-spectrum, primarily bacteriostatic, antibiotic with a range of activity similar to that of chloramphenicol, including many gram-negative and gram-positive organisms; however, florfenicol does not carry the risk of inducing human aplastic anemia that is associated with chloramphenicol. It also has activity against some chloramphenicol resistant strains of bacteria, possibly because it is less affected by the major enzyme produced in plasmid-mediated bacterial resistance against chloramphenicol and thiamphenicol. Although the activity of florfenicol against obligate anaerobes is not addressed in the literature, it is likely to be quite effective. Antibiotic principle of Florfenicol is similar to that of chloramphenicol and Thiamphenicol. Florfenicol inhibits protein synthesis by binding to 70S ribosomal 50S subunits of susceptible bacteria, leading to the inhibition of peptidyl transferase and thereby preventing the transfer of amino acids to extending peptide chains and subsequent protein formation. The bacterial receptor that is the site of action for florfenicol is also considered to be the same as that for chloramphenicol and thiamphenicol. Florfenicol has a fluorine atom instead of the hydroxyl group located at C-3 in the structure of chloramphenicol and thiamphenicol. This prevents the acetylation of bacterial acetyltransferase in this site as to allow florfenicol to be less susceptible to deactivation by bacteria with plasmid-transmissible resistance that involves acetylation of the C-3 hydroxyl group in chloramphenicol and thiamphenicol, and prevents their interaction with bacterial ribosomes.
CNS Activity
Sources: http://aac.asm.org/content/41/9/1991.full.pdf
Curator's Comment: Known to be CNS penetrant in calves. Human data not available
Approval Year
PubMed
Title | Date | PubMed |
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Effects of florfenicol injection on the meat characteristics of the cervical muscles in cattle. | 2002 Jan |
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[Effects of Aeromonas hydrophila biofilm on the drug resistance]. | 2003 Aug |
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Pharmacokinetics and bioavailability of florfenicol following intravenous, intramuscular and oral administrations in rabbits. | 2004 Aug |
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Effects of subinhibitory concentrations of florfenicol on morphology, growth, and viability of Staphylococcus aureus. | 2004 Aug |
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[Antimicrobial susceptibility in vitro of 32 drugs against pig Streptococcus isolates in China]. | 2004 Dec |
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Animal-to-human transmission of Salmonella Typhimurium DT104A variant. | 2004 Dec |
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[Construction of SW480 cell model identifying Shigella virulent genes]. | 2004 Jul |
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Molecular basis of bacterial resistance to chloramphenicol and florfenicol. | 2004 Nov |
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Optimization and validation of a micellar electrokinetic chromatographic method for the analysis of florfenicol. | 2004 Nov 15 |
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Pharmacokinetics of florfenicol in North American elk (Cervus elaphus). | 2004 Oct |
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Characterization of Streptococcus suis serotype 7 isolates from diseased pigs in Denmark. | 2004 Oct 5 |
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Isolation and antimicrobial susceptibilities of bacterial pathogens from bovine pneumonia: 1994--2002. | 2004 Sep |
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Resistance pattern and assessment of phenicol agents' minimum inhibitory concentration in multiple drug resistant Chryseobacterium isolates from fish and aquatic habitats. | 2005 |
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A new mechanism for chloramphenicol, florfenicol and clindamycin resistance: methylation of 23S ribosomal RNA at A2503. | 2005 Aug |
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A survey on antibiotic usage in dairy herds in Pennsylvania. | 2005 Aug |
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Molecular basis of florfenicol-induced increase in adherence of Staphylococcus aureus strain Newman. | 2005 Aug |
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In vitro antimicrobial susceptibility of Mycoplasma mycoides mycoides large colony and Arcanobacterium pyogenes isolated from clinical cases of ulcerative balanitis and vulvitis in Dorper sheep in South Africa. | 2005 Dec |
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Prevalence of antimicrobial resistance genes in Listeria monocytogenes isolated from dairy farms. | 2005 Fall |
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Antimicrobial drug susceptibility of Staphylococcus intermedius clinical isolates from canine pyoderma. | 2005 Feb |
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[Analysis of chloramphenicol, thiamphenicol and florfenicol in chicken by high performance liquid chromatography with electrospray ionization mass spectrometry]. | 2005 Jan |
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The prevalence and antimicrobial susceptibilities of Salmonella and Campylobacter in ducks in Taiwan. | 2005 Jan |
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Pharmacokinetics of florfenicol in the red pacu (Piaractus brachypomus) after single dose intramuscular administration. | 2005 Jun |
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Evaluation of the antimicrobial activity of florfenicol against bacteria isolated from bovine and porcine respiratory disease. | 2005 Mar 20 |
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Plasmid-borne florfenicol resistance in Pasteurella multocida. | 2005 May |
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Standardization of a broth microdilution susceptibility testing method to determine minimum inhibitory concentrations of aquatic bacteria. | 2005 May 20 |
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Influence of clindamycin on the stability of coa and fnbB transcripts and adherence properties of Staphylococcus aureus Newman. | 2005 Nov 1 |
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Determination of florfenicol in fish feed by liquid chromatography. | 2005 Nov-Dec |
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Comparative evaluation between capillary electrophoresis and high-performance liquid chromatography for the analysis of florfenicol in plasma. | 2005 Oct 4 |
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In vitro antimicrobial inhibition profiles of Mycoplasma bovis isolates recovered from various regions of the United States from 2002 to 2003. | 2005 Sep |
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Assessing the effect of a single dose florfenicol treatment in feedlot cattle on the antimicrobial resistance patterns in faecal Escherichia coli. | 2005 Sep-Dec |
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Evaluation of the therapeutic activity of tulathromycin against swine respiratory disease on farms in Europe. | 2005 Summer |
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Comparative efficacy of tulathromycin versus florfenicol and tilmicosin against undifferentiated bovine respiratory disease in feedlot cattle. | 2005 Summer |
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Comparative efficacy of tulathromycin, tilmicosin, and florfenicol in the treatment of bovine respiratory disease in stocker cattle. | 2005 Summer |
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Efficacy of tulathromycin compared with tilmicosin and florfenicol for the control of respiratory disease in cattle at high risk of developing bovine respiratory disease. | 2005 Summer |
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Efficacy of tulathromycin in the treatment and prevention of natural outbreaks of bovine respiratory disease in European cattle. | 2005 Summer |
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Variability in acquired resistance of Pasteurella and Mannheimia isolates from the nasopharynx of calves, with particular reference to different herd types. | 2005 Winter |
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Evaluation of changes in antimicrobial susceptibility patterns of Pasteurella multocida subsp multocida isolates from pigs in Spain in 1987-1988 and 2003-2004. | 2006 Apr |
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Pharmacokinetics of florfenicol in pigs following intravenous, intramuscular or oral administration and the effects of feed intake on oral dosing. | 2006 Apr |
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Role of coresistance in the development of resistance to chloramphenicol in Escherichia coli isolated from sick cattle and pigs. | 2006 Feb |
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Pharmacokinetics of florfenicol and its metabolite, florfenicol amine, in the Korean catfish (Silurus asotus). | 2006 Feb |
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[Simultaneous determination of chloramphenicol, thiamphenicol, and florfenicol residues in animal tissues by gas chromatography/mass spectrometry]. | 2006 Jan |
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Plasmid-mediated florfenicol resistance in Pasteurella trehalosi. | 2006 Jul |
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Comparison of the efficacy of four antimicrobial treatment schemes against experimental Ornithobacterium rhinotracheale infection in turkey poults pre-infected with avian pneumovirus. | 2006 Jun |
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Drug resistance and random amplified polymorphic DNA analysis of Photobacterium damselae ssp. piscicida isolates from cultured Seriola (yellowtail, amberjack and kingfish) in Japan. | 2006 Jun |
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Old dogs that learn new tricks: modified antimicrobial agents that escape pre-existing resistance mechanisms. | 2006 Jun |
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External quality assurance system for antibiotic resistance in bacteria of animal origin in Europe (ARBAO-II), 2003. | 2006 Jun 15 |
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Changes in antimicrobial susceptibility of Actinobacillus pleuropneumoniae isolated from pigs in Spain during the last decade. | 2006 Jun 15 |
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Quantitative susceptibility of Streptococcus suis strains isolated from diseased pigs in seven European countries to antimicrobial agents licensed in veterinary medicine. | 2006 Mar 10 |
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Uptake of veterinary medicines from soils into plants. | 2006 Mar 22 |
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Antimicrobial resistance in bacteria isolated from aquaculture sources in Australia. | 2006 May |
Patents
Sample Use Guides
ONLY for animal: 40 mg florfenicol/kg body weight (6 mL/100 lb)
Route of Administration:
Other
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/7492665
Curator's Comment: Florfenicol showed a high antibacterial activity against A. pleuropneumoniae regardless of the sensitivity of the strains to thiamphenicol.
The minimal inhibitory concentrations of florfenicol against A. pleuropneumoniae ranged from 0.2 to 1.56 ug/ml with a peak at 0.39 ug/ml.
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21 CFR 522.955
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C258
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EMA VETERINARY ASSESSMENT REPORTS |
OSURNIA [AUTHORIZED]
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21 CFR 522.956
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21 CFR 558.261
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EMA VETERINARY ASSESSMENT REPORTS |
ZELERIS [AUTHORIZED]
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21 CFR 524.955
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21 CFR 556.283
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21 CFR 520.955
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21 CFR 524.957
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QJ01BA90
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FLORFENICOL
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ACTIVE MOIETY