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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

Molecular Formula C12H14Cl2FNO4S
Molecular Weight 358.213
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Effects of florfenicol injection on the meat characteristics of the cervical muscles in cattle.
2002 Jan
Chloramphenicol and florfenicol susceptibility of fish-pathogenic bacteria isolated in France: comparison of minimum inhibitory concentration, using recommended provisory standards for fish bacteria.
2003
Bioavailability and pharmacokinetics of florfenicol in broiler chickens.
2003 Oct
Pharmacokinetics of florfenicol in cod Gadus morhua and in vitro antibacterial activity against Vibrio anguillarum.
2003 Sep 24
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
Pharmacokinetics and bioavailability of florfenicol following intravenous, intramuscular and oral administrations in rabbits.
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
[Antimicrobial susceptibility in vitro of 32 drugs against pig Streptococcus isolates in China].
2004 Dec
Animal-to-human transmission of Salmonella Typhimurium DT104A variant.
2004 Dec
Molecular analysis of florfenicol-resistant Escherichia coli isolates from pigs.
2004 Jan
[Construction of SW480 cell model identifying Shigella virulent genes].
2004 Jul
Antibiotic resistance among enterotoxigenic Escherichia coli from piglets and calves with diarrhea.
2004 Jul
Subinhibitory concentrations of florfenicol enhance the adherence of florfenicol-susceptible and florfenicol-resistant Staphylococcus aureus.
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
Optimization and validation of a micellar electrokinetic chromatographic method for the analysis of florfenicol.
2004 Nov 15
Pharmacokinetics of florfenicol in North American elk (Cervus elaphus).
2004 Oct
Isolation and antimicrobial susceptibilities of bacterial pathogens from bovine pneumonia: 1994--2002.
2004 Sep
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
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
Antimicrobial drug susceptibility of Staphylococcus intermedius clinical isolates from canine pyoderma.
2005 Feb
[Analysis of chloramphenicol, thiamphenicol and florfenicol in chicken by high performance liquid chromatography with electrospray ionization mass spectrometry].
2005 Jan
Pharmacokinetics of florfenicol in the red pacu (Piaractus brachypomus) after single dose intramuscular administration.
2005 Jun
Evaluation of the antimicrobial activity of florfenicol against bacteria isolated from bovine and porcine respiratory disease.
2005 Mar 20
Standardization of a broth microdilution susceptibility testing method to determine minimum inhibitory concentrations of aquatic bacteria.
2005 May 20
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
In vitro antimicrobial inhibition profiles of Mycoplasma bovis isolates recovered from various regions of the United States from 2002 to 2003.
2005 Sep
Assessing the effect of a single dose florfenicol treatment in feedlot cattle on the antimicrobial resistance patterns in faecal Escherichia coli.
2005 Sep-Dec
Evaluation of the therapeutic activity of tulathromycin against swine respiratory disease on farms in Europe.
2005 Summer
Comparative efficacy of tulathromycin versus florfenicol and tilmicosin against undifferentiated bovine respiratory disease in feedlot cattle.
2005 Summer
Comparative efficacy of tulathromycin, tilmicosin, and florfenicol in the treatment of bovine respiratory disease in stocker cattle.
2005 Summer
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
Efficacy of tulathromycin in the treatment and prevention of natural outbreaks of bovine respiratory disease in European cattle.
2005 Summer
Variability in acquired resistance of Pasteurella and Mannheimia isolates from the nasopharynx of calves, with particular reference to different herd types.
2005 Winter
Pharmacokinetics of florfenicol in pigs following intravenous, intramuscular or oral administration and the effects of feed intake on oral dosing.
2006 Apr
Role of coresistance in the development of resistance to chloramphenicol in Escherichia coli isolated from sick cattle and pigs.
2006 Feb
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
Old dogs that learn new tricks: modified antimicrobial agents that escape pre-existing resistance mechanisms.
2006 Jun
External quality assurance system for antibiotic resistance in bacteria of animal origin in Europe (ARBAO-II), 2003.
2006 Jun 15
Quantitative susceptibility of Streptococcus suis strains isolated from diseased pigs in seven European countries to antimicrobial agents licensed in veterinary medicine.
2006 Mar 10
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:34:44 UTC 2023
Edited
by admin
on Fri Dec 15 15:34:44 UTC 2023
Record UNII
9J97307Y1H
Record Status Validated (UNII)
Record Version
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Name Type Language
FLORFENICOL
GREEN BOOK   INN   MART.   MI   USAN  
INN   USAN  
Official Name English
FLORFENICOL COMPONENT OF ZELERIS
Brand Name English
NUFLOR
Brand 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
FLORFENICOL COMPONENT OF OSURNIA
Brand Name English
Classification Tree Code System Code
WHO-VATC QJ51BA90
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
CFR 21 CFR 522.955
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
NCI_THESAURUS C258
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
EMA VETERINARY ASSESSMENT REPORTS OSURNIA [AUTHORIZED]
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
CFR 21 CFR 522.956
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
CFR 21 CFR 558.261
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
EMA VETERINARY ASSESSMENT REPORTS ZELERIS [AUTHORIZED]
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
CFR 21 CFR 524.955
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
CFR 21 CFR 556.283
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
CFR 21 CFR 520.955
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
CFR 21 CFR 524.957
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
WHO-VATC QJ01BA90
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
Code System Code Type Description
CHEBI
87185
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
SMS_ID
100000080999
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
NSC
759287
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
DRUG BANK
DB11413
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
FDA UNII
9J97307Y1H
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
PUBCHEM
114811
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
MESH
C035534
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
ChEMBL
CHEMBL1241590
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
MERCK INDEX
m5411
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C75146
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
CAS
73231-34-2
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
DAILYMED
9J97307Y1H
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
USAN
W-75
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
EVMPD
SUB07651MIG
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
INN
5777
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
RXCUI
25086
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID9045500
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
WIKIPEDIA
FLORFENICOL
Created by admin on Fri Dec 15 15:34:44 UTC 2023 , Edited by admin on Fri Dec 15 15:34:44 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY