Enrofloxacin

Enrofloxacin
Clinical data
Trade namesBaytril, others
AHFS/Drugs.comInternational Drug Names
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth, subcutaneous, intramuscular
ATCvet code
Legal status
Legal status
Pharmacokinetic data
Bioavailability80% in dogs, 65-75% in sheep [4]
MetabolismKidney and non-kidney[4]
Elimination half-life4–5 hours in dogs, 6 hours in cats, 1.5 - 4.5 hours in sheep
ExcretionBile duct (70%); kidney (30%)[5]
Identifiers
  • 1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.131.355 Edit this at Wikidata
Chemical and physical data
FormulaC19H22FN3O3
Molar mass359.401 g·mol−1
3D model (JSmol)
Melting point219 to 221 °C (426 to 430 °F)
  • O=C(O)\C3=C\N(c2cc(N1CCN(CC)CC1)c(F)cc2C3=O)C4CC4
  • InChI=1S/C19H22FN3O3/c1-2-21-5-7-22(8-6-21)17-10-16-13(9-15(17)20)18(24)14(19(25)26)11-23(16)12-3-4-12/h9-12H,2-8H2,1H3,(H,25,26) checkY
  • Key:SPFYMRJSYKOXGV-UHFFFAOYSA-N checkY
  (verify)

Enrofloxacin, sold under the brand name Baytril, among others, is a fluoroquinolone antibiotic used for the treatment of animals.[1] It is a bactericidal agent.[1]

The bactericidal activity of enrofloxacin is concentration-dependent, with susceptible bacteria cell death occurring within 20–30 minutes of exposure. Enrofloxacin has demonstrated a significant post-antibiotic effect for both Gram-negative and Gram-positive bacteria and is active in both stationary and growth phases of bacterial replication. Enrofloxacin is partially deethylated by CYP450 into the active metabolite ciprofloxacin, which is also a fluoroquinolone antibiotic.

In September 2005, the FDA withdrew approval of enrofloxacin for use in water to treat flocks of poultry, as the practice was noted to promote the evolution of fluoroquinolone-resistant strains of the bacterium Campylobacter, a human pathogen.[6] Enrofloxacin is available as a fixed-dose combination medication with silver sulfadiazine for the treatment of canine otitis externa.[7] It is available as a generic medication.

Activity and susceptibility data

Enrofloxacin is a synthetic antibacterial agent from the class of the fluoroquinolone carboxylic acid derivatives. It has antibacterial activity against a broad spectrum of Gram-negative and Gram-positive bacteria. It is effective against:

Variable activity against:

Ineffective against:

The following data represent minimum inhibitory concentration ranges for a few medically significant bacterial pathogens:

  • Escherichia coli - 0.022 - 0.03 μg/mL
  • Staphylococcus aureus - 0.0925 - 64 μg/mL
  • Pseudomonas aeruginosa - 0.05 μg/mL

Adverse effects/warnings

Enrofloxacin was banned for poultry use in the United States in 2005.[8]

Overdosage/acute toxicity

It is unlikely that an acute overdose of either compound would result in symptoms more serious than either anorexia or vomiting, but the adverse effects noted above could occur. Dogs receiving 10 times the labeled dosage rate of enrofloxacin for at least 14 days developed only vomiting and anorexia. Death did occur in some dogs when fed 25 times the labeled rate for 11 days, however.

  • Oral LD50: greater than 5000 mg/kg
  • Dermal LD50: greater than 2000 mg/kg
  • Inhalation LD50: greater than 3547 mg/m3 (4-hour exposure)
  • Eye effects: irritant; reversible in less than 7 days.

In cats, enrofloxacin is retinotoxic and can produce sudden-onset blindness, often irreversible.[9][10][11][12][13]

Degradation

The brown rot fungus Gloeophyllum striatum can degrade the fluoroquinolone enrofloxacin using hydroxyl radicals.[14]

References

  1. ^ a b c "Baytril- enrofloxacin injection, solution". DailyMed. 13 October 2022. Retrieved 13 April 2023.
  2. ^ "Baytril- enrofloxacin injection, solution". DailyMed. 22 March 2023. Retrieved 13 April 2023.
  3. ^ "Baytril- enrofloxacin tablet, chewable". DailyMed. 25 November 2021. Retrieved 13 April 2023.
  4. ^ a b Plumb DC. "Enrofloxacin". Veterinary Drug Handbook (fifth ed.).
  5. ^ "Baytril: Excretion and Elimination". Bayer HealthCare AG. Archived from the original on 6 January 2014. Retrieved 6 January 2014.
  6. ^ "Enrofloxacin for Poultry". U.S. Food and Drug Administration (FDA). Archived from the original on 10 February 2007. Retrieved 7 March 2007.
  7. ^ "Baytril Otic- enrofloxacin, silver sulfadiazine emulsion". DailyMed. 27 March 2023. Retrieved 13 April 2023.
  8. ^ Morgan D, Kaufman M (30 April 2005). "Lawmakers' Help for Drug Firm Tests Limits". Washington Post. FDA Calls Efforts For Bayer Illegal
  9. ^ Gelatt KN, van der Woerdt A, Ketring KL, Andrew SE, Brooks DE, Biros DJ, Denis HM, Cutler TJ (June 2001). "Enrofloxacin-associated retinal degeneration in cats". Vet Ophthalmol. 4 (2): 99–106. doi:10.1046/j.1463-5224.2001.00182.x. PMID 11422990.
  10. ^ Wiebe V, Hamilton P (December 2002). "Fluoroquinolone-induced retinal degeneration in cats". J Am Vet Med Assoc. 221 (11): 1568–71. doi:10.2460/javma.2002.221.1568. PMID 12479325.
  11. ^ Grabowski Ł, Gaffke L, Pierzynowska K, Cyske Z, Choszcz M, Węgrzyn G, Węgrzyn A (March 2022). "Enrofloxacin-The Ruthless Killer of Eukaryotic Cells or the Last Hope in the Fight against Bacterial Infections?". Review. Int J Mol Sci. 23 (7): 3648. doi:10.3390/ijms23073648. PMC 8998546. PMID 35409007.
  12. ^ Ramirez CJ, Minch JD, Gay JM, Lahmers SM, Guerra DJ, Haldorson GJ, Schneider T, Mealey KL (February 2011). "Molecular genetic basis for fluoroquinolone-induced retinal degeneration in cats". Pharmacogenet Genomics. 21 (2): 66–75. doi:10.1097/FPC.0b013e3283425f44. PMID 21150813.
  13. ^ Mercer, Melissa A. (September 2022) [2016]. "Quinolones, Including Fluoroquinolones, Use in Animals". MSD Veterinary Manual (11th ed.). Rahway, NJ: Merck & Co., Inc. ISBN 978-0-911-91061-2. Retrieved 8 May 2024.
  14. ^ Wetzstein HG, Schmeer N, Karl W (November 1997). "Degradation of the fluoroquinolone enrofloxacin by the brown rot fungus Gloeophyllum striatum: identification of metabolites". Applied and Environmental Microbiology. 63 (11): 4272–81. Bibcode:1997ApEnM..63.4272W. doi:10.1128/AEM.63.11.4272-4281.1997. PMC 168747. PMID 9361414.