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
Identifiers
  • 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 Edit this at Wikidata
Chemical and physical data
FormulaC12H14Cl2FNO4S
Molar mass358.21 g·mol−1
3D model (JSmol)
  • ClC(Cl)C(=O)N[C@@H]([C@H](O)c1ccc(cc1)S(=O)(=O)C)CF
  • 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 brand name Nuflor) is a fluorinated synthetic analog of thiamphenicol,[1] mainly used as a antibiotic in veterinary medicine.

Florfenicol is available a generic medication.[2]

Veterinary uses

In the United States, florfenicol is 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 Prevotella melaninogenica.

In swine, it is indicated for the treatment of respiratory infections caused by Actinobacillus pleuropneumoniae, Bordetella bronchiseptica, Glaesserella parasuis, P. multocida, and Streptococcus suis.

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 has been used in the Europe Union,[4] treating mainly primary or secondary colibacillosis in broiler[5] and parent flocks.

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]

In November 2024, the US Food and Drug Administration approved Paqflor (florfenicol), the first generic florfenicol drug for controlling mortality in certain species of freshwater-reared fish.[7] Paqflor contains the same active ingredient (florfenicol) as the approved brand name drug product, Aquaflor, which was first approved in October 2005.[7] In addition, the FDA determined that Paqflor contains no inactive ingredients that may significantly affect the bioavailability of the active ingredient.[7] Paqflor is indicated for freshwater-reared salmonids: for the control of mortality due to furunculosis associated with Aeromonas salmonicida. For the control of mortality due to coldwater disease associated with Flavobacterium psychrophilum; freshwater-reared finfish: for the control of mortality due to columnaris disease associated with Flavobacterium columnare; catfish: for the control of mortality due to enteric septicemia of catfish associated with Edwardsiella ictaluri; freshwater-reared warmwater finfish: for the control of mortality due to streptococcal septicemia associated with Streptococcus iniae.[8][9]

Contamination

Florfenicol was among the drug contaminants in a brand of supermarket eggs in Taiwan and Iran.[10]

References

  1. ^ Syriopoulou VP, Harding AL, Goldmann DA, Smith AL (February 1981). "In vitro antibacterial activity of fluorinated analogs of chloramphenicol and thiamphenicol". Antimicrobial Agents and Chemotherapy. 19 (2): 294–297. doi:10.1128/aac.19.2.294. PMC 181412. PMID 6957162.
  2. ^ "Florfenicol". Drugs.com.
  3. ^ Gaunt PS, Langston C, Wrzesinski C, Gao D, Adams P, Crouch L, et al. (October 2013). "Multidose pharmacokinetics of orally administered florfenicol in the channel catfish (Ictalurus punctatus)". Journal of Veterinary Pharmacology and Therapeutics. 36 (5): 502–506. doi:10.1111/j.1365-2885.2012.01426.x. PMID 22882087.{{cite journal}}: CS1 maint: overridden setting (link)
  4. ^ "Florfenicol (Extension to Chicken)" (PDF). Committee for Veterinary Medicinal Products. European Medicines Agency. March 1999. Archived from the original (PDF) on 20 September 2018. Retrieved 10 May 2016.
  5. ^ Shen J, Wu X, Hu D, Jiang H (October 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. ^ Magdesian KG (2009). "Update on Common Antimicrobials". In Robinson NE, Sprayberry KA (eds.). Current therapy in equine medicine. Saunders Elesevier. p. 13. ISBN 978-1-4160-5475-7. Retrieved 21 March 2011.
  7. ^ a b c "FDA Approves First Generic Florfenicol for Controlling Mortality in Freshwater-reared Fish". U.S. Food and Drug Administration (FDA). 14 November 2024. Retrieved 21 December 2024. Public Domain This article incorporates text from this source, which is in the public domain.
  8. ^ "Recent Animal Drug Approvals". U.S. Food and Drug Administration (FDA). 2 December 2024. Retrieved 21 December 2024. Public Domain This article incorporates text from this source, which is in the public domain.
  9. ^ https://animaldrugsatfda.fda.gov/adafda/app/search/public/document/downloadFoi/16248
  10. ^ I-chia L (8 January 2013). "Survey suggests certain eggs may be dangerous". Taipei Times. Retrieved 3 November 2014.