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{{Short description|Chemical compound}} |
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{{drugbox | verifiedrevid = 420247316 |
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{{More citations needed|date=November 2016}} |
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{{Use dmy dates|date=April 2023}} |
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| IUPAC_name = 1-Cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolonecarboxylic acid |
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{{Drugbox |
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| image = Enrofloxacin Structural Formulae.png |
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| verifiedrevid = 443725793 |
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| IUPAC_name = 1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid |
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| image = Enrofloxacin structure.svg |
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<!--Clinical data--> |
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| tradename = Baytril, others |
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| Drugs.com = {{drugs.com|international|enrofloxacin}} |
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| DailyMedID = Enrofloxacin |
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| pregnancy_AU = B3 |
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| routes_of_administration = ], ], ] |
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| ATCvet = yes |
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| ATCvet = yes |
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| ATC_prefix = J01 |
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| ATC_prefix = J01 |
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| ATC_suffix = MA90 |
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| ATC_suffix = MA90 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| ATC_supplemental = {{ATCvet|D06|BA51}} |
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| legal_AU = S4 |
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| legal_UK = POM |
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| legal_US = Rx-only |
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| legal_US_comment = <ref name="Baytril FDA label">{{cite web | title=Baytril- enrofloxacin injection, solution | website=DailyMed | date=13 October 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=258967db-9587-4c19-b846-ac143dada99a | access-date=13 April 2023}}</ref><ref>{{cite web | title=Baytril- enrofloxacin injection, solution | website=DailyMed | date=22 March 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a1ada9f6-24e2-4287-8b83-00e2b68666e5 | access-date=13 April 2023}}</ref><ref>{{cite web | title=Baytril- enrofloxacin tablet, chewable | website=DailyMed | date=25 November 2021 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=606b1dd3-24ed-4f8c-8885-6b22fd7b8883 | access-date=13 April 2023}}</ref> |
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<!--Pharmacokinetic data--> |
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| bioavailability = 80% in dogs, 65-75% in sheep <ref name="autogenerated1">{{cite book | vauthors = Plumb DC | chapter = Enrofloxacin | title = Veterinary Drug Handbook | edition = fifth }}</ref> |
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| metabolism = ] and non-kidney<ref name="autogenerated1"/> |
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| elimination_half-life = 4–5 hours in dogs, 6 hours in cats, 1.5 - 4.5 hours in sheep |
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| excretion = ] (70%); ] (30%)<ref>{{cite web | title = Baytril: Excretion and Elimination |url=http://www.animalhealth.bayer.com/5175.0.html | publisher = Bayer HealthCare AG |access-date=2014-01-06 |url-status=dead |archive-url=https://web.archive.org/web/20140106234031/http://www.animalhealth.bayer.com/5175.0.html |archive-date=2014-01-06 }}</ref> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 93106-60-6 |
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| PubChem = 71188 |
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| DrugBank_Ref = |
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| DrugBank = DB11404 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 64326 |
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| ChemSpiderID = 64326 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 3DX3XEK1BN |
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| UNII = 3DX3XEK1BN |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| 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) |
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| KEGG = D02473 |
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| smiles = O=C(O)\C3=C\N(c2cc(N1CCN(CC)CC1)c(F)cc2C3=O)C4CC4 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| InChIKey = SPFYMRJSYKOXGV-UHFFFAOYAN |
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| ChEBI = 35720 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 15511 |
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| ChEMBL = 15511 |
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<!--Chemical data--> |
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| C=19 | H=22 | F=1 | N=3 | O=3 |
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| smiles = O=C(O)\C3=C\N(c2cc(N1CCN(CC)CC1)c(F)cc2C3=O)C4CC4 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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) |
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| 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) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = SPFYMRJSYKOXGV-UHFFFAOYSA-N |
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| StdInChIKey = SPFYMRJSYKOXGV-UHFFFAOYSA-N |
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| melting_point = 219 |
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| CAS_number = 93106-60-6 |
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| ChEBI = 35720 |
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| melting_high = 221 |
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| PubChem = 71188 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D02473 |
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| C=19|H=22|F=1|N=3|O=3 |
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| molecular_weight = 359.4 |
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| bioavailability = 80% in dogs, 65-75% in sheep <ref>Plumb DC. ''Enrofloxacin.'' Veterinary Drug Handbook, fifth edition.</ref> |
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| protein_bound = |
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| metabolism = Renal and non-renal<ref>Plumb DC. ''Enrofloxacin.'' Veterinary Drug Handbook, fifth edition.</ref> |
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| elimination_half-life = 4–5 hours in dogs, 6 hours in cats, 1.5 - 4.5 hours in sheep. |
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| excretion = Renal |
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| pregnancy_AU = B3 |
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| pregnancy_US = C |
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| legal_AU = S4 |
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| legal_UK = POM |
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| routes_of_administration = ], subcutaneous injection, ] (]s) |
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}} |
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}} |
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'''Enrofloxacin''', sold under the brand name '''Baytril''', among others, is a ] antibiotic used for the treatment of animals.<ref name="Baytril FDA label" /> It is a ] agent.<ref name="Baytril FDA label" /> |
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'''Enrofloxacin''' is a ] antibiotic sold by the ] under the trade name '''Baytril'''. Enrofloxacin is currently ]-approved for 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 '']'', 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 ] are widely used in the treatment of human disease. |
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It is a ] 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 ] and ] bacteria and is active in both stationary and growth phases of bacterial replication. |
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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 ] and ] bacteria and is active in both stationary and growth phases of bacterial replication. Enrofloxacin is partially deethylated by CYP450 into the active metabolite ], which is also a fluoroquinolone antibiotic. |
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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 '']'', a human pathogen.<ref>{{cite web |url=https://www.fda.gov/cvm/FQWithdrawal.html |title=Enrofloxacin for Poultry | publisher = U.S. ] (FDA) |access-date=2007-03-07 |url-status=dead |archive-url=https://web.archive.org/web/20070210231646/https://www.fda.gov/cvm/FQWithdrawal.html |archive-date=2007-02-10 }}</ref> Enrofloxacin is available as a ] medication with ] for the treatment of canine otitis externa.<ref>{{cite web | title=Baytril Otic- enrofloxacin, silver sulfadiazine emulsion | website=DailyMed | date=27 March 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5012fe70-6394-45f5-be75-04297e39574d | access-date=13 April 2023}}</ref> It is available as a ]. |
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==Activity== |
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'''Enrofloxacin''' is a synthetic chemotherapeutic agent from the class of the ] carboxylic acid derivatives. It has antibacterial activity against a broad spectrum of ] and ] bacteria. Its mechanism of action is not thoroughly understood, but it is believed to act by inhibiting bacterial ] (a type-II ]), thereby preventing DNA supercoiling and DNA synthesis. It is effective against: |
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==Activity and susceptibility data== |
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Enrofloxacin is a synthetic antibacterial agent from the class of the ] carboxylic acid derivatives. It has antibacterial activity against a broad spectrum of ] and ] bacteria. It is effective against: |
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Ineffective against anaerobes |
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Ineffective against: |
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* ]s |
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The following data represent minimum inhibitory concentration ranges for a few medically significant bacterial pathogens: |
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==Contraindications/precautions== |
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* ''Escherichia coli'' - 0.022 - 0.03 μg/mL |
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High drug resistance. |
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* ''Staphylococcus aureus'' - 0.0925 - 64 μg/mL |
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* ''Pseudomonas aeruginosa'' - 0.05 μg/mL |
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==Adverse effects/warnings== |
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==Adverse effects/warnings== |
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* Permanent blindness and vision loss have been reported with ], including enrofloxacin.<ref>http://www.fda.gov/cvm/Documents/baytrilDDL.pdf</ref> Enrofloxacin was banned for poultry use in 2005 <ref>Washington Post, April 30, 2005 FDA Calls Efforts For Bayer Illegal |
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Lawmakers' Help for Drug Firm Tests Limits Dan Morgan and Marc Kaufman</ref> |
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Enrofloxacin was banned for poultry use in the United States in 2005.<ref>{{cite news | url = https://www.washingtonpost.com/wp-dyn/content/article/2005/04/29/AR2005042901349.html | newspaper = Washington Post | date = April 30, 2005 | quote = FDA Calls Efforts For Bayer Illegal | title = Lawmakers' Help for Drug Firm Tests Limits | vauthors = Morgan D, Kaufman M }}</ref> |
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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. |
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==Overdosage/acute toxicity== |
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==Overdosage/acute toxicity== |
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* Dermal LD<sub>50</sub>: greater than 2000 mg/kg |
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* Dermal LD<sub>50</sub>: greater than 2000 mg/kg |
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* Inhalation LD<sub>50</sub>: greater than 3547 mg/m3 (4-hour exposure) |
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* Inhalation LD<sub>50</sub>: greater than 3547 mg/m3 (4-hour exposure) |
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* Eye effects: irritant; reversible in less than 7 days. In cats, it can produce sudden onset blindness when administered by injection, as it is retinotoxic. |
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* Eye effects: irritant; reversible in less than 7 days. |
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In cats, enrofloxacin is retinotoxic and can produce sudden-onset blindness, often irreversible.<ref>{{cite journal |vauthors=Gelatt KN, van der Woerdt A, Ketring KL, Andrew SE, Brooks DE, Biros DJ, Denis HM, Cutler TJ |title=Enrofloxacin-associated retinal degeneration in cats |journal=Vet Ophthalmol |volume=4 |issue=2 |pages=99–106 |date=June 2001 |pmid=11422990 |doi=10.1046/j.1463-5224.2001.00182.x}}</ref><ref>{{cite journal |vauthors=Wiebe V, Hamilton P |title=Fluoroquinolone-induced retinal degeneration in cats |journal=J Am Vet Med Assoc |volume=221 |issue=11 |pages=1568–71 |date=December 2002 |pmid=12479325 |doi=10.2460/javma.2002.221.1568}}</ref><ref>{{cite journal |vauthors=Grabowski Ł, Gaffke L, Pierzynowska K, Cyske Z, Choszcz M, Węgrzyn G, Węgrzyn A |title=Enrofloxacin-The Ruthless Killer of Eukaryotic Cells or the Last Hope in the Fight against Bacterial Infections? |department=Review |journal=Int J Mol Sci |volume=23 |issue=7 |date=March 2022 |page=3648 |pmid=35409007 |pmc=8998546 |doi=10.3390/ijms23073648|doi-access=free }}</ref><ref>{{cite journal |vauthors=Ramirez CJ, Minch JD, Gay JM, Lahmers SM, Guerra DJ, Haldorson GJ, Schneider T, Mealey KL |title=Molecular genetic basis for fluoroquinolone-induced retinal degeneration in cats |journal=Pharmacogenet Genomics |volume=21 |issue=2 |pages=66–75 |date=February 2011 |pmid=21150813 |doi=10.1097/FPC.0b013e3283425f44}}</ref><ref>{{cite book |last1=Mercer |first1=Melissa A. |title=MSD Veterinary Manual |title-link=Merck Manual of Diagnosis and Therapy#The Merck Veterinary Manual |edition=11th |publisher=Merck & Co., Inc. |location=Rahway, NJ |orig-date=2016 |date=September 2022 |chapter=Quinolones, Including Fluoroquinolones, Use in Animals |chapter-url=https://www.msdvetmanual.com/pharmacology/antibacterial-agents/quinolones,-including-fluoroquinolones,-use-in-animals |access-date=2024-05-08 |isbn=978-0-911-91061-2}}</ref> |
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==See also== |
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==References== |
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==Degradation== |
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The brown rot fungus ''] striatum'' can degrade the fluoroquinolone enrofloxacin using hydroxyl radicals.<ref>{{cite journal | vauthors = Wetzstein HG, Schmeer N, Karl W | title = Degradation of the fluoroquinolone enrofloxacin by the brown rot fungus Gloeophyllum striatum: identification of metabolites | journal = Applied and Environmental Microbiology | volume = 63 | issue = 11 | pages = 4272–81 | date = November 1997 | pmid = 9361414 | pmc = 168747 | doi = 10.1128/AEM.63.11.4272-4281.1997 | bibcode = 1997ApEnM..63.4272W }} |
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{{reflist}} |
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</ref> |
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== References == |
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{{Reflist}} |
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{{QuinoloneAntiBiotics}} |
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{{QuinoloneAntiBiotics}} |
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