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 60 Target ID: CHEMBL2311224 Sources: http://file.scirp.org/pdf/OJVM_2016022615035704.pdf	Inhibitor 8146
Topoisomerase IV 59 Target ID: CHEMBL2363076 Sources: http://file.scirp.org/pdf/OJVM_2016022615035704.pdf	Inhibitor 8146

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 231 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/UCM062413.pdf	Curative		Approved 8307	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
Interaction of fluoroquinolones and certain ionophores in broilers: effect on blood levels and hepatic cytochrome p450 monooxygenase activity.	2001	11791885
Pharmacokinetics of enrofloxacin and its metabolite ciprofloxacin after intramuscular administration of enrofloxacin in goats.	2001 Apr	11334149
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
In vitro susceptibility of avian mycoplasmas to enrofloxacin, sarafloxacin, tylosin, and oxytetracycline.	2001 Apr-Jun	11417828
Multiresidue analysis of fluoroquinolone antibiotics in chicken tissue using automated microdialysis-liquid chromatography.	2001 Aug	11513278
Determination of residues of enrofloxacin and its metabolite ciprofloxacin in biological materials by capillary electrophoresis.	2001 Aug 5	11499631
Susceptibility of Arcobacter butzleri isolates to 23 antimicrobial agents.	2001 Dec	11737626
Information on adverse drug reaction in cats.	2001 Dec 15	11767912
Epidemiological studies of human and animal Salmonella typhimurium DT104 and DT104b isolates in Ireland.	2001 Feb	11293679
Antibiotic resistance from down on the chicken farm.	2001 Jan-Feb	11930916
Pathogenicity and drug susceptibility of the Pasteurella anatis isolated in chickens in Taiwan.	2001 Jul-Sep	11569739
The effect of organic acids on the control of post-weaning oedema disease of piglets.	2001 Jun	11676628
In vitro antibacterial activity of enrofloxacin and ciprofloxacin in combination against Escherichia coli and staphylococcal clinical isolates from dogs.	2001 Jun	11676620
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
A microbiological six-plate method for the identification of certain antibiotic groups in incurred kidney and muscle samples.	2001 May	11394306
In vitro antibiotic sensitivity of strains of Ornithobacterium rhinotracheale isolated in The Netherlands between 1996 and 1999.	2001 Nov 17	11761291
Prevalence and mechanism of resistance against macrolides and lincosamides in Streptococcus suis isolates.	2001 Nov 26	11574176
Bioequivalence of four preparations of enrofloxacin in poultry.	2001 Oct	11696080
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
Effect of enrofloxacin treatment on plasma endotoxin during bovine Escherichia coli mastitis.	2002 Apr	12058958
Salmonella enterica serotype Typhimurium DT 104 antibiotic resistance genomic island I in serotype paratyphi B.	2002 Apr	11971780
Serovars of Salmonella isolated from Danish turkeys between 1995 and 2000 and their antimicrobial resistance.	2002 Apr 13	11995678
Questions study on Escherichia coli susceptibility.	2002 Apr 15	11990957
Multiresidue determination of (fluoro)quinolone antibiotics in swine kidney using liquid chromatography-tandem mass spectrometry.	2002 Apr 5	12064523
Anticryptosporidial prophylactic efficacy of enrofloxacin and paromomycin in chickens.	2002 Feb	12053972
Comparative serum pharmacokinetics of the fluoroquinolones enrofloxacin, difloxacin, marbofloxacin, and orbifloxacin in dogs after single oral administration.	2002 Feb	11874520
Prevalence and antibiotic susceptibility of Salmonella isolated from beef animal hides and carcasses.	2002 Feb	11848559
History and clinical signs.	2002 Feb	11842601
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
Blindness now attributed to enrofloxacin therapy in a previously reported case of a cat with acromegaly treated by cryohypophysectomy.	2002 Jan	11802672
Pharmacokinetics of enrofloxacin and its metabolite ciprofloxacin in goats given enrofloxacin alone and in combination with probenecid.	2002 Jan	11749141
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
Antibiotic resistance. Livestock feed ban preserves drugs' power.	2002 Jan 4	11778017
Use of enrofloxacin for treatment of large-form Haemobartonella felis in experimentally infected cats.	2002 Jul 15	12118588
Antimicrobial multiresistance in bacteria isolated from freshwater Chilean salmon farms.	2002 Jul 3	12109474
Identification and antimicrobial susceptibility of Staphylococcus chromogenes isolates from intramammary infections of dairy cows.	2002 Jun 20	12034545
Molecular epidemiology of feline bordetellosis in two animal shelters in California, USA.	2002 Jun 25	12069777
Concentration of enrofloxacin and its metabolite ciprofloxacin in canine matrices of the locomotor system.	2002 Mar	11958474
Antimicrobial susceptibility of Actinobacillus pleuropneumoniae, Escherichia coli, and Salmonella choleraesuis recovered from Taiwanese swine.	2002 Mar	11939337
Feline visual changes associated with enrofloxacin.	2002 Mar	11901587
Ciprofloxacin resistance in Campylobacter jejuni evolves rapidly in chickens treated with fluoroquinolones.	2002 Mar 15	11920303
Administration of enrofloxacin and capsaicin to chickens to achieve higher maximal serum concentrations.	2002 Mar 16	11936887
Bacterial colonization of intravenous catheters in young dogs suspected to have parvoviral enteritis.	2002 May 1	11991409
Sero types, phage types and antibiotic susceptibilities of Salmonella strains isolated from horses in The Netherlands from 1993 to 2000.	2002 May 1	11900955

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 `Fri Dec 16 18:00:21 UTC 2022` Edited by `admin` on `Fri Dec 16 18:00:21 UTC 2022`
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