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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
Structure of FLORFENICOL

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

HIDE SMILES / InChI
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

Curator's Comment: Known to be CNS penetrant in calves. Human data not available

Approval Year

PubMed

PubMed

TitleDatePubMed
Multidrug-resistant Salmonella typhimurium and Salmonella enteritidis identified by multiplex PCR from animals.
2001 Dec
Prevalence of Salmonella and E. coli, and their resistance to antimicrobial agents, in farming communities in northern Thailand.
2002
An evaluation of the relative efficacy of a new formulation of oxytetracycline for the treatment of undifferentiated fever in feedlot calves in western Canada.
2002 Dec
Clinical efficacy of florfenicol in the treatment of calf respiratory tract infections.
2002 Feb
Effects of florfenicol injection on the meat characteristics of the cervical muscles in cattle.
2002 Jan
Comparative in vitro activity of 16 antimicrobial agents against Actinobacillus pleuropneumoniae.
2002 Jan
Liquid chromatographic determination of florfenicol in the plasma of multiple species of fish.
2002 Nov 15
Pharmacokinetics of florfenicol in healthy and Escherichia coli-infected broiler chickens.
2002 Oct
Tissue pharmacokinetics of florfenicol in pigs experimentally infected with Actinobacillus pleuropneumoniae.
2002 Oct-Dec
In vitro sensitivity of Hungarian Actinobaculum suis strains to selected antimicrobials.
2003
Florfenicol resistance in Salmonella enterica serovar Newport mediated by a plasmid related to R55 from Klebsiella pneumoniae.
2003 Apr
Stability of florfenicol in drinking water.
2003 Jan-Feb
Genome analysis of F. nucleatum sub spp vincentii and its comparison with the genome of F. nucleatum ATCC 25586.
2003 Jun
Pharmacokinetics of florfenicol in loggerhead sea turtles (Caretta caretta) after single intravenous and intramuscular injections.
2003 Mar
Variant Salmonella genomic island 1 antibiotic resistance gene cluster in Salmonella enterica serovar Albany.
2003 May
Determination of florfenicol amine in channel catfish muscle by liquid chromatography.
2003 May-Jun
In vitro evaluation of the susceptibility of Edwardsiella ictaluri, etiological agent of enteric septicemia in channel catfish, Ictalurus punctatus (Rafinesque), to florfenicol.
2003 Nov
Salmonella agona harboring genomic island 1-A.
2004 Apr
Plasmid-mediated florfenicol and ceftriaxone resistance encoded by the floR and bla(CMY-2) genes in Salmonella enterica serovars Typhimurium and Newport isolated in the United States.
2004 Apr 15
Effects of subinhibitory concentrations of florfenicol on morphology, growth, and viability of Staphylococcus aureus.
2004 Aug
Intravenous and subcutaneous pharmacokinetics of florfenicol in sheep.
2004 Aug
Monitoring of florfenicol susceptibility among bovine and porcine respiratory tract pathogens collected in Germany during the years 2002 and 2003.
2004 Aug
Antibiotic resistance among enterotoxigenic Escherichia coli from piglets and calves with diarrhea.
2004 Jul
Characterization of florfenicol resistance among calf pathogenic Escherichia coli.
2004 Jul 15
Bioavailability and pharmacokinetics of florfenicol in healthy sheep.
2004 Jun
Use of florfenicol in non-human primates.
2004 Jun
Molecular basis of bacterial resistance to chloramphenicol and florfenicol.
2004 Nov
Characterization of Streptococcus suis serotype 7 isolates from diseased pigs in Denmark.
2004 Oct 5
Resistance pattern and assessment of phenicol agents' minimum inhibitory concentration in multiple drug resistant Chryseobacterium isolates from fish and aquatic habitats.
2005
A new mechanism for chloramphenicol, florfenicol and clindamycin resistance: methylation of 23S ribosomal RNA at A2503.
2005 Aug
A survey on antibiotic usage in dairy herds in Pennsylvania.
2005 Aug
Molecular basis of florfenicol-induced increase in adherence of Staphylococcus aureus strain Newman.
2005 Aug
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
Prevalence of antimicrobial resistance genes in Listeria monocytogenes isolated from dairy farms.
2005 Fall
[Analysis of chloramphenicol, thiamphenicol and florfenicol in chicken by high performance liquid chromatography with electrospray ionization mass spectrometry].
2005 Jan
Evaluation of the antimicrobial activity of florfenicol against bacteria isolated from bovine and porcine respiratory disease.
2005 Mar 20
Plasmid-borne florfenicol resistance in Pasteurella multocida.
2005 May
Standardization of a broth microdilution susceptibility testing method to determine minimum inhibitory concentrations of aquatic bacteria.
2005 May 20
Influence of clindamycin on the stability of coa and fnbB transcripts and adherence properties of Staphylococcus aureus Newman.
2005 Nov 1
Determination of florfenicol in fish feed by liquid chromatography.
2005 Nov-Dec
Comparative evaluation between capillary electrophoresis and high-performance liquid chromatography for the analysis of florfenicol in plasma.
2005 Oct 4
Efficacy of tulathromycin in the treatment and prevention of natural outbreaks of bovine respiratory disease in European cattle.
2005 Summer
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
Pharmacokinetics of florfenicol and its metabolite, florfenicol amine, in the Korean catfish (Silurus asotus).
2006 Feb
[Simultaneous determination of chloramphenicol, thiamphenicol, and florfenicol residues in animal tissues by gas chromatography/mass spectrometry].
2006 Jan
Plasmid-mediated florfenicol resistance in Pasteurella trehalosi.
2006 Jul
Comparison of the efficacy of four antimicrobial treatment schemes against experimental Ornithobacterium rhinotracheale infection in turkey poults pre-infected with avian pneumovirus.
2006 Jun
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
External quality assurance system for antibiotic resistance in bacteria of animal origin in Europe (ARBAO-II), 2003.
2006 Jun 15
Changes in antimicrobial susceptibility of Actinobacillus pleuropneumoniae isolated from pigs in Spain during the last decade.
2006 Jun 15
Patents

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
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.
Name Type Language
FLORFENICOL
GREEN BOOK   INN   MART.   MI   USAN  
INN   USAN  
Official Name English
NUFLOR
Preferred Name English
D-THREO-2,2-DICHLORO-N-(.ALPHA.-(FLUOROMETHYL)-.BETA.-HYDROXY-P-(METHYLSULFONYL)PHENETHYL)ACETAMIDE
Common Name English
SCH-25298
Code English
ACETAMIDE, 2,2-DICHLORO-N-(1-(FLUOROMETHYL)-2-HYDROXY-2-(4-(METHYLSULFONYL)PHENYL)ETHYL)-, (R-(R*,S*))-
Common Name English
SCH 25298
Code English
FLORFENICOL [MI]
Common Name English
2,2-DICHLORO-N-((.ALPHA.S,.BETA.R)-.ALPHA.-(FLUOROMETHYL)-.BETA.-HYDROXY-P-(METHYLSULFONYL)PHENETHYL)ACETAMIDE
Common Name English
FLORFENICOL [USAN]
Common Name English
FLORFENICOL [JAN]
Common Name English
florfenicol [INN]
Common Name English
FLORFENICOL [MART.]
Common Name English
ZELERIS COMPONENT FLORFENICOL
Brand Name English
FLORFENICOL [GREEN BOOK]
Common Name English
OSURNIA COMPONENT FLORFENICOL
Brand Name English
NSC-759287
Code English
FLORFENICOL [EMA EPAR VETERINARY]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ51BA90
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
CFR 21 CFR 522.955
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
NCI_THESAURUS C258
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
EMA VETERINARY ASSESSMENT REPORTS OSURNIA [AUTHORIZED]
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
CFR 21 CFR 522.956
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
CFR 21 CFR 558.261
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
EMA VETERINARY ASSESSMENT REPORTS ZELERIS [AUTHORIZED]
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
CFR 21 CFR 524.955
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
CFR 21 CFR 556.283
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
CFR 21 CFR 520.955
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
CFR 21 CFR 524.957
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
WHO-VATC QJ01BA90
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
Code System Code Type Description
CHEBI
87185
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
SMS_ID
100000080999
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
NSC
759287
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
DRUG BANK
DB11413
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
FDA UNII
9J97307Y1H
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
PUBCHEM
114811
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
MESH
C035534
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
ChEMBL
CHEMBL1241590
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
MERCK INDEX
m5411
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C75146
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
CAS
73231-34-2
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
DAILYMED
9J97307Y1H
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
USAN
W-75
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
EVMPD
SUB07651MIG
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
INN
5777
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
RXCUI
25086
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID9045500
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY
WIKIPEDIA
FLORFENICOL
Created by admin on Mon Mar 31 18:01:46 GMT 2025 , Edited by admin on Mon Mar 31 18:01:46 GMT 2025
PRIMARY