ENROFLOXACIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H22FN3O3
Molecular Weight	359.3947
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1CCN(CC1)C2=CC3=C(C=C2F)C(=O)C(=CN3C4CC4)C(O)=O

InChI

InChIKey=SPFYMRJSYKOXGV-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C19H22FN3O3
Molecular Weight	359.3947
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/UCM062413.pdf
Curator's Comment: description was created based on several sources, including, http://file.scirp.org/pdf/OJVM_2016022615035704.pdf, https://actualidadveterinaria.files.wordpress.com/2011/10/fluoroquinolones-then-and-now.pdf

Enrofloxacin was developed by Bayer for the treatment of broad spectrum of bacterial infections in animals (cats and dogs). The drug exerts its action by inhibiting DNA Topoisomerase II (Gyrase) and DNA Topoisomerase IV (Topo IV), two major bacterial topoisomerase. Enrofloxacin was shown to be metabolized to ciprofloxacin and may cross the blood brain barrier in the animals.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 64 Target ID: CHEMBL2311224 Sources: http://file.scirp.org/pdf/OJVM_2016022615035704.pdf	Inhibitor 8228
Topoisomerase IV 62 Target ID: CHEMBL2363076 Sources: http://file.scirp.org/pdf/OJVM_2016022615035704.pdf	Inhibitor 8228

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 232 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/UCM062413.pdf	Curative		Approved 8360	BAYTRIL Approved Use Baytril Antibacterial Tablets and Injectable Solution are indicated for the management of diseases in dogs and cats associated with bacteria susceptible to enrofloxacin. Launch Date 1.14048002E12

PubMed

Title	Date	PubMed
Mutant prevention concentration as a measure of fluoroquinolone potency against mycobacteria.	2000 Dec	11083637
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.	2000 Oct	10991858
Interaction of fluoroquinolones and certain ionophores in broilers: effect on blood levels and hepatic cytochrome p450 monooxygenase activity.	2001	11791885
Antibacterial drugs prescribed for dogs and cats in Sweden and Norway 1990-1998.	2001	11455899
Characterisation of some Ornithobacterium rhinotracheale strains and examination of their transmission via eggs.	2001	11402640
Antimicrobial susceptibility of intestinal bacteria from Swiss poultry flocks before the ban of antimicrobial growth promoters.	2001 Apr	11403390
Hypoadrenocorticism in a cat.	2001 Apr	11327666
Diagnosis and treatment of conjunctivitis in house finches associated with mycoplasmosis in Minnesota.	2001 Apr	11310874
Determination of fluoroquinolones in serum using an on-line clean-up column coupled to high-performance immunoaffinity-reversed-phase liquid chromatography.	2001 Apr 15	11318402
Effects of the matrix and sample preparation on the determination of fluoroquinolone residues in animal tissues.	2001 Apr 20	11358236
Monitoring Mycoplasma gallisepticum and Mycoplasma synoviae infection in breeder chickens after treatment with enrofloxacin.	2001 Apr-Jun	11417841
Determination of residues of enrofloxacin and its metabolite ciprofloxacin in biological materials by capillary electrophoresis.	2001 Aug 5	11499631
Organic acid profiles in feces of pigs with pathogenic or non-pathogenic diarrhea.	2001 Dec	11789618
Epidemiological studies of human and animal Salmonella typhimurium DT104 and DT104b isolates in Ireland.	2001 Feb	11293679
Effects of enrofloxacin and magnesium deficiency on matrix metabolism in equine articular cartilage.	2001 Feb	11212020
Nonenteric Escherichia coli isolates from dogs: 674 cases (1990-1998).	2001 Feb 1	11201564
Pharmacokinetics of enrofloxacin after intravenous and intramuscular administration in Angora goats.	2001 Jan	11227198
Effect of enrofloxacin-Na against pathogens related to the respiratory and alimentary diseases in suckling and weanling piglets.	2001 Jan	11217067
Non-bioequivalence of various trademarks of enrofloxacin and Baytril in cows.	2001 Jul	11505850
Activity and postantibiotic effect of marbofloxacin, enrofloxacin, difloxacin and ciprofloxacin against feline Bordetella bronchiseptica isolates.	2001 Jul 3	11356321
The use of antibiotics critical to human medicine in food-producing animals in Taiwan.	2001 Jun	11456367
Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998.	2001 Mar	11315521
Development of an indirect competitive ELISA for ciprofloxacin residues in food animal edible tissues.	2001 Mar	11312816
In vitro evidence for effects of magnesium supplementation on quinolone-treated horse and dog chondrocytes.	2001 Mar	11280370
Addressing the use of fluoroquinolone antibiotics in agriculture.	2001 Mar	11236459
Characterization of high-level fluoroquinolone resistance in Escherichia coli O78:K80 isolated from turkeys.	2001 Mar	11222567
Effects of an experimental infection with Actinobacillus pleuropneumoniae on the interferon-alpha and interleukin-6 producing capacity of porcine peripheral blood mononuclear cells stimulated with bacteria, virus or plasmid DNA.	2001 Mar 20	11230938
Serogroups and antimicrobial susceptibility among Escherichia coli isolated from farmed mink (Mustela vison Schreiber) in Denmark.	2001 Mar 20	11230936
Inhibition tests for detection and presumptive identification of tetracyclines, beta-lactam antibiotics and quinolones in poultry meat.	2001 May	11358180
Effects of enrofloxacin and ciprofloxacin hydrochloride on canine and equine chondrocytes in culture.	2001 May	11341389
In vitro susceptibility to 15 antibiotics of vibrios isolated from penaeid shrimps in Northwestern Mexico.	2001 May	11337225
Absorption spectra of the 4f electron transitions of the praseodymium complex with 1-cyclopropyl-6-fluoro-1,4-dihydro-7-(4-ethyl-1-piperazinyl) -4-oxo-3-quinoline carboxylic acid hydrochloride and its analytical application.	2001 Sep	11708065
Antimicrobial susceptibility of Pasteurella multocida isolated from cattle and pigs.	2001 Sep	11666039
Antimicrobial susceptibility of udder pathogens isolated from dairy herds in the west littoral region of Uruguay.	2002	12071114
Biofilm bacteria: formation and comparative susceptibility to antibiotics.	2002 Apr	11989739
Questions study on Escherichia coli susceptibility.	2002 Apr 15	11990957
Idiosyncratic reaction to enrofloxacin in cats.	2002 Apr 27	12019544
In vitro development of resistance to enrofloxacin, erythromycin, tylosin, tiamulin and oxytetracycline in Mycoplasma gallisepticum, Mycoplasma iowae and Mycoplasma synoviae.	2002 Aug 2	12119137
Comparative serum pharmacokinetics of the fluoroquinolones enrofloxacin, difloxacin, marbofloxacin, and orbifloxacin in dogs after single oral administration.	2002 Feb	11874520
Using nonaqueous capillary electrophoresis to analyze several quinolones in pig kidney samples.	2002 Feb	11870754
Elimination of mycoplasma from leukemia-lymphoma cell lines using antibiotics.	2002 Feb	11840296
Monoclonal-based enzyme-linked immunosorbent assay and immunochromatographic assay for enrofloxacin in biological matrices.	2002 Jan	11827405
Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae.	2002 Jan	11821174
Susceptibility of human isolates of Salmonella typhimurium DT 104 to antimicrobial agents used in human and veterinary medicine.	2002 Jan	11821166
Spectrophotometric determination of ciprofloxacin, enrofloxacin and pefloxacin through charge transfer complex formation.	2002 Jan 1	11682219
Enrofloxacin resistance in Escherichia coli isolated from dogs with urinary tract infections.	2002 Jan 15	12126128
Pathotypes of avian Escherichia coli as related to tsh-, pap-, pil-, and iuc-DNA sequences, and antibiotic sensitivity of isolates from internal tissues and the cloacae of broilers.	2002 Jan-Mar	11922326
Pharmacokinetics after intravenous and oral administration of enrofloxacin in sheep.	2002 Jul	12118662
Antimicrobial susceptibility of Actinobacillus pleuropneumoniae, Escherichia coli, and Salmonella choleraesuis recovered from Taiwanese swine.	2002 Mar	11939337
Bayer seeks veterinary, industry backing before Baytril hearing.	2002 May 15	12018362

Patents

Sample Use Guides

In Vivo Use Guide

The dose range of Baytril (Enrofloxacin) Antibacterial Tablets in dogs and cats is 5 to 20 mg/kg (2.27 to 9.07 mg/lb) of body weight, either as a single dose or divided into two (2) equal daily doses administered at twelve (12) hour intervals. The dose of Baytril Injectable Solution for dogs is 2.5 mg/kg (1.13 mg/lb) as a single injection. The injectable dose should be followed by oral tablet treatment in 12 hours.

Route of Administration: Other

In Vitro Use Guide

The minimum inhibitory concentration (MIC) enrofloxacin against 24 Sicilian isolates of Mycoplasma agalactiae, the causative organism of contagious agalactia were determined in vitro by a broth dilution method. Enrofloxacin was effective antimicrobial in vitro with a range of MIC values from 0.125 to 0.500 microg/ml and an MIC(50) of 0.203 and MIC(90) of 0.365 microg/ml.

Substance Class	Chemical Created by `admin` on `Wed Jul 05 23:12:38 UTC 2023` Edited by `admin` on `Wed Jul 05 23:12:38 UTC 2023`
Record UNII	3DX3XEK1BN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENROFLOXACIN

Official Name

English

ENROFLOXACIN [USP MONOGRAPH]

Common Name

English

ENROFLOXACIN [HSDB]

Common Name

English

ENROFLOXACIN [MI]

Common Name

English

ENROFLOXACIN FOR VETERINARY USE [EP MONOGRAPH]

Common Name

English

ENROFLOXACIN FOR VETERINARY USE [EP IMPURITY]

Common Name

English

ENROFLOXACIN [USP IMPURITY]

Common Name

English

BAYTRIL

Brand Name

English

ENROFLOXACIN [GREEN BOOK]

Common Name

English

ENROFLOXACIN [USP-RS]

Common Name

English

ENROFLOXACIN [USAN]

Common Name

English

ENROFLOXACIN [MART.]

Common Name

English

ENROFLOXACIN FOR VETERINARY USE

Common Name

English

BAY VP 2674

Code

English

enrofloxacin [INN]

Common Name

English

1-Cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Systematic Name

English

NSC-758616

Code

English

Classification Tree Code System Code

WHO-VATC

QJ01MA90