Enrofloxacin: Difference between revisions

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{{SI}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 443725793
| IUPAC_name = 1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
| image = En.png


<!--Clinical data-->
| tradename = 
| Drugs.com = {{drugs.com|international|enrofloxacin}}
| pregnancy_AU = B3
| pregnancy_US = C
| legal_AU = S4
| legal_UK = POM
| routes_of_administration = [[Route of administration#Enteral|Oral]], subcutaneous injection,  [[topical]] ([[ear drop]]s)


'''Enrofloxacin''' is a [[fluoroquinolone]] antibiotic sold by the [[Bayer|Bayer Corporation]] under the trade name '''Baytril'''. Enrofloxacin is currently [[Food and Drug Administration|FDA]]-approved for treatment of individual pets and domestic animals in the United States. In September of 2005, the FDA withdrew approval of Baytril for use in water to treat flocks of poultry, as this practice was noted to promote the evolution of fluoroquinolone-resistant strains of the bacterium ''[[Campylobacter]]'', a human pathogen.<ref>http://www.fda.gov/cvm/FQWithdrawal.html FDA statement on withdrawal of Baytril for use in poultry</ref> Fluoroquinolones such as [[ciprofloxacin]] are widely used in the treatment of human disease.
<!--Pharmacokinetic data-->
| bioavailability = 80% in dogs, 65-75% in sheep <ref>Plumb DC. ''Enrofloxacin.'' Veterinary Drug Handbook, fifth edition.</ref>
| metabolism = Renal and non-renal<ref>Plumb DC. ''Enrofloxacin.'' Veterinary Drug Handbook, fifth edition.</ref>
| elimination_half-life = 4–5 hours in dogs, 6 hours in cats, 1.5 - 4.5 hours in sheep.
| excretion = Bile (70%); Renal (30%)<ref>http://www.animalhealth.bayer.com/5175.0.html</ref>
 
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 93106-60-6
| ATCvet = yes
| ATC_prefix = J01
| ATC_suffix = MA90
| PubChem = 71188
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 64326
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3DX3XEK1BN
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02473
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 35720
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 15511
 
<!--Chemical data-->
| C=19 | H=22 | F=1 | N=3 | O=3
| molecular_weight = 359.4
| smiles = O=C(O)\C3=C\N(c2cc(N1CCN(CC)CC1)c(F)cc2C3=O)C4CC4
| InChI = 1/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)
| InChIKey = SPFYMRJSYKOXGV-UHFFFAOYAN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SPFYMRJSYKOXGV-UHFFFAOYSA-N
}}
 
'''Enrofloxacin''' is a [[fluoroquinolone]] antibiotic sold by the [[Bayer|Bayer Corporation]] under the trade name '''Baytril'''. Enrofloxacin is currently approved by the [[Food and Drug Administration|FDA]] for the treatment of individual pets and domestic animals in the United States. In September 2005, the FDA withdrew approval of Baytril for use in water to treat flocks of poultry, as this practice was noted to promote the evolution of fluoroquinolone-resistant strains of the bacterium ''[[Campylobacter]]'', a human pathogen.<ref>http://www.fda.gov/cvm/FQWithdrawal.html FDA statement on withdrawal of Baytril for use in poultry</ref>  
 
It is a [[bactericidal]] agent. 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.
 
==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. Its mechanism of action is not thoroughly understood, but it is believed to act by inhibiting bacterial [[DNA gyrase]] (a type-II [[topoisomerase]]), thereby preventing DNA supercoiling and DNA synthesis. It is effective against:
* ''[[Pseudomonas aeruginosa]]''
* ''[[Klebsiella]]''
* ''[[Escherichia coli]]''
* ''[[Enterobacter]]''
* ''[[Campylobacter]]''
* ''[[Shigella]]''
* ''[[Salmonella]]''
* ''[[Aeromonas]]''
* ''[[Haemophilus]]''
* ''[[Proteus (bacterium)|Proteus]]''
* ''[[Yersinia]]''
* ''[[Serratia]]''
* ''[[Vibrio]]''
* ''[[Brucella]]''
* ''[[Chlamydia trachomatis]]''
* ''[[Staphylococcus]]'' (including penicillinase-producing and methicillin-resistant strains)
* ''[[Mycoplasma]]''
* ''[[Mycobacterium]]''
 
Variable activity against:
* ''[[Streptococcus]]''
 
Ineffective against:
* [[Anaerobic organism|Anaerobe]]s
 
 
The following data represent minimum inhibitory concentration ranges for a few medically significant bacterial pathogens:
* ''Escherichia coli'' - 0.004 - 512 µg/ml
* ''Staphylococcus aureus'' - 0.0925 - 64 µg/ml
* ''Pseudomonas aeruginosa'' - 0.05 µg/ml <ref>http://antibiotics.toku-e.com/antimicrobial_588_1.html</ref>
 
==Contraindications/precautions==
Usage in poultry.
 
==Adverse effects/warnings==
 
Enrofloxacin was banned for poultry use in 2005.<ref>Washington Post, April 30, 2005 FDA Calls Efforts For Bayer Illegal
Lawmakers' Help for Drug Firm Tests Limits Dan Morgan and Marc Kaufman</ref>  Baytril should not be used in rapidly growing animals (for example dogs under 12 months - 18 months in large breeds, or kittens under 8 weeks) as it causes abnormalities in the development of articular cartilage.{{citation needed|date=December 2014}}
 
==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&nbsp;mg/kg
* Dermal LD<sub>50</sub>: greater than 2000&nbsp;mg/kg
* Inhalation LD<sub>50</sub>: greater than 3547&nbsp;mg/m3 (4-hour exposure)
* Eye effects: irritant; reversible in less than 7 days.  In cats, it can produce sudden onset blindness when administered by injection, as
 
==Degradation==
 
The brown rot fungus ''[[Gloeophyllum]] striatum'' can degrade the fluoroquinolone enrofloxacin using hydroxyl radicals. <ref> {{citejournal|url=http://www.ncbi.nlm.nih.gov/pubmed/9361414|title=Degradation of the fluoroquinolone enrofloxacin by the brown rot fungus Gloeophyllum striatum: identification of metabolites|author1=Wetzstein HG|author2=Schmeer N|author3=Karl W|journal=Applied Environmental Biology|volume=63|page=4272-81}}
</ref>


==References==
==References==
{{reflist}}
{{reflist}}


 
{{QuinoloneAntiBiotics}}


[[Category:Fluoroquinolone antibiotics]]
[[Category:Fluoroquinolone antibiotics]]
 
[[Category:Veterinary drugs]]
 
[[Category:Piperazines]]
[[de:Enrofloxacin]]
[[Category:Cyclopropanes]]
{{WH}}
{{WikiDoc Sources}}

Latest revision as of 19:27, 6 April 2015

Enrofloxacin
Clinical data
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • AU: B3
  • US: C (Risk not ruled out)
Routes of
administration		Oral, subcutaneous injection, topical (ear drops)
ATCvet code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability80% in dogs, 65-75% in sheep [2]
MetabolismRenal and non-renal[1]
Elimination half-life4–5 hours in dogs, 6 hours in cats, 1.5 - 4.5 hours in sheep.
ExcretionBile (70%); Renal (30%)[3]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC19H22FN3O3
Molar mass359.4
3D model (JSmol)
  (verify)

Enrofloxacin is a fluoroquinolone antibiotic sold by the Bayer Corporation under the trade name Baytril. Enrofloxacin is currently approved by the FDA for the treatment of individual pets and domestic animals in the United States. In September 2005, the FDA withdrew approval of Baytril for use in water to treat flocks of poultry, as this practice was noted to promote the evolution of fluoroquinolone-resistant strains of the bacterium Campylobacter, a human pathogen.[4]

It is a bactericidal agent. 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.

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. Its mechanism of action is not thoroughly understood, but it is believed to act by inhibiting bacterial DNA gyrase (a type-II topoisomerase), thereby preventing DNA supercoiling and DNA synthesis. 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 - 0.004 - 512 µg/ml
  • Staphylococcus aureus - 0.0925 - 64 µg/ml
  • Pseudomonas aeruginosa - 0.05 µg/ml [5]

Contraindications/precautions

Usage in poultry.

Adverse effects/warnings

Enrofloxacin was banned for poultry use in 2005.[6] Baytril should not be used in rapidly growing animals (for example dogs under 12 months - 18 months in large breeds, or kittens under 8 weeks) as it causes abnormalities in the development of articular cartilage.[citation needed]

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 Template: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, it can produce sudden onset blindness when administered by injection, as

Degradation

The brown rot fungus Gloeophyllum striatum can degrade the fluoroquinolone enrofloxacin using hydroxyl radicals. [7]

References

  1. ↑ Plumb DC. Enrofloxacin. Veterinary Drug Handbook, fifth edition.
  2. ↑ Plumb DC. Enrofloxacin. Veterinary Drug Handbook, fifth edition.
  3. ↑ http://www.animalhealth.bayer.com/5175.0.html
  4. ↑ http://www.fda.gov/cvm/FQWithdrawal.html FDA statement on withdrawal of Baytril for use in poultry
  5. ↑ http://antibiotics.toku-e.com/antimicrobial_588_1.html
  6. ↑ Washington Post, April 30, 2005 FDA Calls Efforts For Bayer Illegal Lawmakers' Help for Drug Firm Tests Limits Dan Morgan and Marc Kaufman
  7. ↑ Template:Citejournal

Template:QuinoloneAntiBiotics

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