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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
ONLY for animal: 40 mg florfenicol/kg body weight (6 mL/100 lb)
Route of Administration: Other
In Vitro Use Guide
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
Record UNII
9J97307Y1H
Record Status Validated (UNII)
Record Version