Florfenicol

Florfenicol

Systematic (IUPAC) name
2,2-dichloro-N-[(1R,2S)-3-fluoro-1-hydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	intramuscular, subcutaneous
Legal status	veterinary prescription only
Identifiers
CAS Number	73231-34-2
ATCvet code	QJ01BA90(WHO) QJ51BA90
PubChem	CID 114811
ChemSpider	102776
UNII	9J97307Y1H
KEGG	D04194
ChEBI	CHEBI:87185
ChEMBL	CHEMBL1241590
Synonyms	2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(methylsulfonyl)phenyl)propan-2-yl)ethanamide
Chemical data
Formula	C12H14Cl2FNO4S
Molar mass	358.21 g/mol
SMILES ClC(Cl)C(=O)N[C@@H]([C@H](O)c1ccc(cc1)S(=O)(=O)C)CF
InChI 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 Key:AYIRNRDRBQJXIF-NXEZZACHSA-N
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Florfenicol (marketed by Schering-Plough Animal Health under the trade name Nuflor) is a fluorinated synthetic analog of thiamphenicol.^[1]

In the United States, florfenicol is currently 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 also used in aquaculture, and is licensed for use in the United States for the control of enteric septicemia in catfish.^[2]

The use of florfenicol in horses, and likely in other equids, typically causes diarrhea. This has been anecdotally reported to progress to lethal cases of acute colitis. Therefore, use of this antimicrobial in the equine patient should be limited to cases in which other, safer, options are not available. ^[3]

Contamination

Florfenicol was among the drug contaminants in a brand of supermarket eggs in Taiwan and Iran.^[4]

External links

• Nuflor website

References

1. Syriopoulou VP, Harding AL, Goldmann DA, Smith AL (February 1981). "In vitro antibacterial activity of fluorinated analogs of chloramphenicol and thiamphenicol.". Antimicrob Agents Chemother. 19 (2): 294–7. PMC 181412. PMID 6957162.
2. Gaunt, P. S.; Langston, C.; Wrzesinski, C.; Gao, D.; Adams, P.; Crouch, L.; Sweeney, D.; Endris, R. "Multidose pharmacokinetics of orally administered florfenicol in the channel catfish ( )". Journal of Veterinary Pharmacology and Therapeutics 36 (5): 502–506. doi:10.1111/j.1365-2885.2012.01426.x.
3. Robinson, N.E.; Sprayberry, K.A. (2009). Current therapy in equine medicine. Saunders Elesevier. p. 13. ISBN 978-1-4160-5475-7. Retrieved March 21, 2011.
4. Lee I-chia (8 January 2013). "Survey suggests certain eggs may be dangerous". Taipei Times. Retrieved 3 November 2014.