From Wikipedia, the free encyclopedia
Chemical compound
Enrofloxacin
![](//upload.wikimedia.org/wikipedia/commons/thumb/a/ad/Enrofloxacin_structure.svg/220px-Enrofloxacin_structure.svg.png) |
|
Trade names
| Baytril, others
|
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AHFS
/
Drugs.com
| International Drug Names
|
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License data
|
|
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Pregnancy
category
| |
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Routes of
administration
| By mouth
,
subcutaneous
,
intramuscular
|
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ATCvet code
| |
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|
Legal status
|
|
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|
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]
|
---|
|
1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
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CAS Number
| |
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PubChem
CID
| |
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ChemSpider
| |
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UNII
| |
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KEGG
| |
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ChEBI
| |
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ChEMBL
| |
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CompTox Dashboard
(
EPA
)
| |
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ECHA InfoCard
| 100.131.355
![Edit this at Wikidata](//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png) |
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Formula
| C
19
H
22
F
N
3
O
3
|
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Molar mass
| 359.401
g·mol
?1
|
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3D model (
JSmol
)
| |
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Melting point
| 219 to 221 °C (426 to 430 °F)
|
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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)
Y
Key:SPFYMRJSYKOXGV-UHFFFAOYSA-N
Y
|
(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
[
edit
]
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
[
edit
]
Enrofloxacin was banned for poultry use in the United States in 2005.
[8]
Overdosage/acute toxicity
[
edit
]
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
LD
50
: greater than 5000 mg/kg
- Dermal LD
50
: greater than 2000 mg/kg
- Inhalation LD
50
: 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
[
edit
]
The brown rot fungus
Gloeophyllum
striatum
can degrade the fluoroquinolone enrofloxacin using hydroxyl radicals.
[14]
References
[
edit
]
- ^
a
b
c
"Baytril- enrofloxacin injection, solution"
.
DailyMed
. 13 October 2022
. Retrieved
13 April
2023
.
- ^
"Baytril- enrofloxacin injection, solution"
.
DailyMed
. 22 March 2023
. Retrieved
13 April
2023
.
- ^
"Baytril- enrofloxacin tablet, chewable"
.
DailyMed
. 25 November 2021
. Retrieved
13 April
2023
.
- ^
a
b
Plumb DC. "Enrofloxacin".
Veterinary Drug Handbook
(fifth ed.).
- ^
"Baytril: Excretion and Elimination"
. Bayer HealthCare AG. Archived from
the original
on 6 January 2014
. Retrieved
6 January
2014
.
- ^
"Enrofloxacin for Poultry"
. U.S.
Food and Drug Administration
(FDA). Archived from
the original
on 10 February 2007
. Retrieved
7 March
2007
.
- ^
"Baytril Otic- enrofloxacin, silver sulfadiazine emulsion"
.
DailyMed
. 27 March 2023
. Retrieved
13 April
2023
.
- ^
Morgan D, Kaufman M (30 April 2005).
"Lawmakers' Help for Drug Firm Tests Limits"
.
Washington Post
.
FDA Calls Efforts For Bayer Illegal
- ^
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
.
- ^
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
.
- ^
Grabowski Ł, Gaffke L, Pierzynowska K, Cyske Z, Choszcz M, W?grzyn G, W?grzyn 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
.
- ^
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
.
- ^
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
.
- ^
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
.