Enrofloxacin

Last updated

Enrofloxacin
Enrofloxacin structure.svg
Clinical data
Trade names Baytril, others
AHFS/Drugs.com International Drug Names
License data
Pregnancy
category
  • AU:B3
Routes of
administration
By mouth, subcutaneous, intramuscular
ATCvet code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 80% in dogs, 65-75% in sheep [4]
Metabolism Kidney and non-kidney [4]
Elimination half-life 4–5 hours in dogs, 6 hours in cats, 1.5 - 4.5 hours in sheep
Excretion Bile 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
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.131.355 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H22FN3O3
Molar mass 359.401 g·mol−1
3D model (JSmol)
Melting point 219 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) Yes check.svgY
  • Key:SPFYMRJSYKOXGV-UHFFFAOYSA-N Yes check.svgY
   (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]

Contents

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:

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.

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]

Related Research Articles

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<span class="mw-page-title-main">Aztreonam</span> Chemical compound

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<span class="mw-page-title-main">Campylobacteriosis</span> Infection by Campylobacter bacteria

Campylobacteriosis is among the most common infections caused by a bacterium in humans, often as a foodborne illness. It is caused by the Campylobacter bacterium, most commonly C. jejuni. It produces an inflammatory, sometimes bloody, diarrhea or dysentery syndrome, and usually cramps, fever and pain.

<span class="mw-page-title-main">Colistin</span> Antibiotic

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<span class="mw-page-title-main">Ofloxacin</span> Antibiotic to treat bacterial infections

Ofloxacin is a quinolone antibiotic useful for the treatment of a number of bacterial infections. When taken by mouth or injection into a vein, these include pneumonia, cellulitis, urinary tract infections, prostatitis, plague, and certain types of infectious diarrhea. Other uses, along with other medications, include treating multidrug resistant tuberculosis. An eye drop may be used for a superficial bacterial infection of the eye and an ear drop may be used for otitis media when a hole in the ear drum is present.

<span class="mw-page-title-main">Tobramycin</span> Chemical compound

Tobramycin is an aminoglycoside antibiotic derived from Streptomyces tenebrarius that is used to treat various types of bacterial infections, particularly Gram-negative infections. It is especially effective against species of Pseudomonas.

<span class="mw-page-title-main">Marbofloxacin</span> Chemical compound

Marbofloxacin is a carboxylic acid derivative third generation fluoroquinolone antibiotic. It is used in veterinary medicine under the brand names Marbocyl, Forcyl, Marbo vet and Zeniquin. A formulation of marbofloxacin combined with clotrimazole and dexamethasone is available under the name Aurizon.

<span class="mw-page-title-main">Apramycin</span> Chemical compound

Apramycin is an aminoglycoside antibiotic used in veterinary medicine. It is produced by Streptomyces tenebrarius.

<span class="mw-page-title-main">Enoxacin</span> Chemical compound

Enoxacin is an oral broad-spectrum fluoroquinolone antibacterial agent used in the treatment of urinary tract infections and gonorrhea. Insomnia is a common adverse effect. It is no longer available in the United States.

<span class="mw-page-title-main">Cefoxitin</span> Chemical compound

Cefoxitin is a second-generation cephamycin antibiotic developed by Merck & Co., Inc. from Cephamycin C in the year following its discovery, 1972. It was synthesized in order to create an antibiotic with a broader spectrum. It is often grouped with the second-generation cephalosporins. Cefoxitin requires a prescription and as of 2010 is sold under the brand name Mefoxin by Bioniche Pharma, LLC. The generic version of cefoxitin is known as cefoxitin sodium.

<span class="mw-page-title-main">Prulifloxacin</span> Chemical compound

Prulifloxacin is an older synthetic antibiotic of the fluoroquinolone class undergoing clinical trials prior to a possible NDA submission to the U.S. Food and Drug Administration (FDA). It is a prodrug which is metabolized in the body to the active compound ulifloxacin. It was developed over two decades ago by Nippon Shinyaku Co. and was patented in Japan in 1987 and in the United States in 1989.

<span class="mw-page-title-main">Difloxacin</span> Chemical compound

Difloxacin (INN), marketed under the trade name Dicural, is a second-generation, synthetic fluoroquinolone antibiotic used in veterinary medicine. It has broad-spectrum, concentration dependent, bactericidal activity; however, its efficacy is not as good as enrofloxacin or pradofloxacin.

<span class="mw-page-title-main">Pradofloxacin</span> Chemical compound

Pradofloxacin, sold under the brand name Veraflox among others, is a third-generation enhanced spectrum veterinary antibiotic of the fluoroquinolone class. It was developed by Elanco Animal Health GmbH and received approval from the European Commission in April 2011, for prescription-only use in veterinary medicine for the treatment of bacterial infections in dogs and cats.

<span class="mw-page-title-main">Delafloxacin</span> Chemical compound

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Infections caused by exposure to ionizing radiation can be extremely dangerous, and are of public and government concern. Numerous studies have demonstrated that the susceptibility of organisms to systemic infection increased following exposure to ionizing radiation. The risk of systemic infection is higher when the organism has a combined injury, such as a conventional blast, thermal burn, or radiation burn. There is a direct quantitative relationship between the magnitude of the neutropenia that develops after exposure to radiation and the increased risk of developing infection. Because no controlled studies of therapeutic intervention in humans are available, almost all of the current information is based on animal research.

<span class="mw-page-title-main">Ceftolozane/tazobactam</span> Antibiotic

Ceftolozane/tazobactam, sold under the brand name Zerbaxa, is a fixed-dose combination antibiotic medication used for the treatment of complicated urinary tract infections and complicated intra-abdominal infections in adults. Ceftolozane is a cephalosporin antibiotic, developed for the treatment of infections with gram-negative bacteria that are resistant to conventional antibiotics. It was studied for urinary tract infections, intra-abdominal infections and ventilator-associated bacterial pneumonia.

<span class="mw-page-title-main">Finafloxacin</span> Chemical compound

Finafloxacin (Xtoro) is a fluoroquinolone antibiotic. In the United States, it is approved by the Food and Drug Administration to treat acute otitis externa caused by the bacteria Pseudomonas aeruginosa and Staphylococcus aureus.

<span class="mw-page-title-main">Murepavadin</span> Chemical compound

Murepavadin also known as POL7080 is a Pseudomonas specific peptidomimetic antibiotic. It is a synthetic cyclic beta hairpin peptidomimetic based on the cationic antimicrobial peptide protegrin I (PG-1) and the first example of an outer membrane protein-targeting antibiotic class with a novel, nonlytic mechanism of action, highly active and selective against the protein transporter LptD of Pseudomonas aeruginosa. In preclinical studies the compound was highly active on a broad panel of clinical isolates including multi-drug resistant Pseudomonas bacteria with outstanding in vivo efficacy in sepsis, lung, and thigh infection models. Intravenous murepavadin is in development for the treatment of bacterial hospital-acquired pneumonia and bacterial ventilator-associated pneumonia due to Pseudomonas aeruginosa.

<span class="mw-page-title-main">Cefiderocol</span> Antibiotic

Cefiderocol, sold under the brand name Fetroja among others, is an antibiotic used to treat complicated urinary tract infections when no other options are available. It is indicated for the treatment of multi-drug-resistant Gram-negative bacteria including Pseudomonas aeruginosa. It is given by injection into a vein.

References

  1. 1 2 3 "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. 1 2 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.