Florfenicol

Florfenicol
Structural formula
Ball-and-stick model of florfenicol
Clinical data
Trade namesNuflor
Other names2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(methylsulfonyl)phenyl)propan-2-yl)ethanamide
AHFS/Drugs.comInternational Drug Names
Routes of
administration		intramuscular, subcutaneous
ATCvet code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • Veterinary use only
Identifiers
IUPAC name
  • 2,2-dichloro-N-[(1R,2S)-3-fluoro-1-hydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.170.898
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Chemical and physical data
FormulaC12H14Cl2FNO4S
Molar mass358.21 g·mol−1
3D model (JSmol)
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 checkY
  • Key:AYIRNRDRBQJXIF-NXEZZACHSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Florfenicol (marketed by Schering-Plough Animal Health under the trade name Nuflor) is a fluorinated synthetic analog of thiamphenicol,[1] mainly used in veterinary medicine.

As a generic, it is now available worldwide.[2]

Indications

In the United States, florfenicol is currently indicated for the treatment of bovine respiratory disease (BRD) associated with Mannheimia haemolytica, Pasteurella multocida, and Histophilus somni, 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.[3]

Since the early 2000s, it is used in Europe,[4] treating mainly primary or secondary colibacillosis in broiler[5] and parent flocks. It is not allowed in laying hens, due to residues in eggs. It is also indicated in turkey.

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.[6]

Contamination

Florfenicol was among the drug contaminants in a brand of supermarket eggs in Taiwan and Iran.[7]

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. doi:10.1128/aac.19.2.294. PMC 181412. PMID 6957162.
  2. ↑ "Florfenicol".
  3. ↑ Gaunt, P. S.; Langston, C.; Wrzesinski, C.; Gao, D.; Adams, P.; Crouch, L.; Sweeney, D.; Endris, R. (2013). "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. PMID 22882087.
  4. ↑ http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500014277.pdf
  5. ↑ Shen, J.; Wu, X.; Jiang, H. (2002). "Pharmacokinetics of florfenicol in healthy and Escherichia coli-infected broiler chickens". Research in Veterinary Science. 73 (2): 137–140. doi:10.1016/s0034-5288(02)00033-4. PMID 12204631.
  6. ↑ 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.
  7. ↑ Lee I-chia (8 January 2013). "Survey suggests certain eggs may be dangerous". Taipei Times. Retrieved 3 November 2014.
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