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 66 Target ID: CHEMBL2311224 Sources: http://file.scirp.org/pdf/OJVM_2016022615035704.pdf	Inhibitor 8504
Topoisomerase IV 62 Target ID: CHEMBL2363076 Sources: http://file.scirp.org/pdf/OJVM_2016022615035704.pdf	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/UCM062413.pdf	Curative		Approved 8583	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 2006

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2E1 1060 CYP2C19 2057 CYP2A6 879 BSEP 550 CYP1A2 2153 CYP19A1 429 P-gp 1741 BCRP 910	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71188#section=Biological-Test-Results Page: 25.0	no [IC50 23.7101 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1NTExIn19	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1NTExIn19	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1NTExIn19	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1NTExIn19	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTU1MTEifX0=	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1NTExIn19	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTU1MTEifX0=	no [IC50 >10 uM]
BSEP 554	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MDIwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1NTExIn19	no [IC50 >1000 uM]
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71188#section=BioAssay-Results Page: 74.0	no
MRP1 232	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71188#section=BioAssay-Results Page: 56.0	no
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71188#section=BioAssay-Results Page: 76.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71188#section=BioAssay-Results Page: 482.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiKkNIRU1CTDE1NTExIn19

PubMed

Title	Date	PubMed
In vitro development of resistance to enrofloxacin, erythromycin, tylosin, tiamulin and oxytetracycline in Mycoplasma gallisepticum, Mycoplasma iowae and Mycoplasma synoviae.	2002-08-02	12119137
The use of liposomal enrofloxacin for intracellular infections in Kangal dogs and visualization of phagocytosis of liposomes.	2002-08	12007205
Use of enrofloxacin for treatment of large-form Haemobartonella felis in experimentally infected cats.	2002-07-15	12118588
Antimicrobial multiresistance in bacteria isolated from freshwater Chilean salmon farms.	2002-07-03	12109474
Pharmacokinetics after intravenous and oral administration of enrofloxacin in sheep.	2002-07	12118662
Molecular epidemiology of feline bordetellosis in two animal shelters in California, USA.	2002-06-25	12069777
Identification and antimicrobial susceptibility of Staphylococcus chromogenes isolates from intramammary infections of dairy cows.	2002-06-20	12034545
LC determination of enrofloxacin.	2002-06-15	12049983
Determination of ciprofloxacin, enrofloxacin and flumequine in pig plasma samples by capillary isotachophoresis--capillary zone electrophoresis.	2002-05-25	12016028
Bayer seeks veterinary, industry backing before Baytril hearing.	2002-05-15	12018362
Bacterial colonization of intravenous catheters in young dogs suspected to have parvoviral enteritis.	2002-05-01	11991409
Sero types, phage types and antibiotic susceptibilities of Salmonella strains isolated from horses in The Netherlands from 1993 to 2000.	2002-05-01	11900955
In vitro antimicrobial susceptibility of 183 Pseudomonas aeruginosa strains isolated from dogs to selected antipseudomonal agents.	2002-05	12069272
Idiosyncratic reaction to enrofloxacin in cats.	2002-04-27	12019545
Idiosyncratic reaction to enrofloxacin in cats.	2002-04-27	12019544
Questions study on Escherichia coli susceptibility.	2002-04-15	11990957
Serovars of Salmonella isolated from Danish turkeys between 1995 and 2000 and their antimicrobial resistance.	2002-04-13	11995678
Multiresidue determination of (fluoro)quinolone antibiotics in swine kidney using liquid chromatography-tandem mass spectrometry.	2002-04-05	12064523
Antibiotic resistance from down on the chicken farm.	2002-04-05	11930916
Effect of antibiotics on in vitro and in vivo avian cartilage degradation.	2002-04-02	11922351
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.	2002-04-02	11922326
Spectrophotometric determination of enrofloxacin and pefloxacin through ion-pair complex formation.	2002-04-01	11861121
Effect of enrofloxacin treatment on plasma endotoxin during bovine Escherichia coli mastitis.	2002-04	12058958
Bacterial resistance to quinolone antibiotics in Poland.	2002-04	12019949
Biofilm bacteria: formation and comparative susceptibility to antibiotics.	2002-04	11989739
Salmonella enterica serotype Typhimurium DT 104 antibiotic resistance genomic island I in serotype paratyphi B.	2002-04	11971780
Influence of porcine Actinobacillus pleuropneumoniae infection and dexamethasone on the pharmacokinetic parameters of enrofloxacin.	2002-04	11907176
Administration of enrofloxacin and capsaicin to chickens to achieve higher maximal serum concentrations.	2002-03-16	11936887
Ciprofloxacin resistance in Campylobacter jejuni evolves rapidly in chickens treated with fluoroquinolones.	2002-03-15	11920303
Concentration of enrofloxacin and its metabolite ciprofloxacin in canine matrices of the locomotor system.	2002-03	11958474
Antimicrobial susceptibility of Actinobacillus pleuropneumoniae, Escherichia coli, and Salmonella choleraesuis recovered from Taiwanese swine.	2002-03	11939337
Feline visual changes associated with enrofloxacin.	2002-03	11901587
Anticryptosporidial prophylactic efficacy of enrofloxacin and paromomycin in chickens.	2002-02	12053972
Comparative antibiotic eradication of mycoplasma infections from continuous cell lines.	2002-02	11929000
Comparative serum pharmacokinetics of the fluoroquinolones enrofloxacin, difloxacin, marbofloxacin, and orbifloxacin in dogs after single oral administration.	2002-02	11874520
Using nonaqueous capillary electrophoresis to analyze several quinolones in pig kidney samples.	2002-02	11870754
Prevalence and antibiotic susceptibility of Salmonella isolated from beef animal hides and carcasses.	2002-02	11848559
History and clinical signs.	2002-02	11842601
Elimination of mycoplasma from leukemia-lymphoma cell lines using antibiotics.	2002-02	11840296
Enrofloxacin resistance in Escherichia coli isolated from dogs with urinary tract infections.	2002-01-15	12126128
Antibiotic resistance. Livestock feed ban preserves drugs' power.	2002-01-04	11778017
Comparative in vitro activity of 16 antimicrobial agents against Actinobacillus pleuropneumoniae.	2002-01	11860083
Monoclonal-based enzyme-linked immunosorbent assay and immunochromatographic assay for enrofloxacin in biological matrices.	2002-01	11827405
Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae.	2002-01	11821174
Susceptibility of human isolates of Salmonella typhimurium DT 104 to antimicrobial agents used in human and veterinary medicine.	2002-01	11821166
Blindness now attributed to enrofloxacin therapy in a previously reported case of a cat with acromegaly treated by cryohypophysectomy.	2002-01	11802672
Antimicrobial susceptibility of udder pathogens isolated from dairy herds in the west littoral region of Uruguay.	2002	12071114
Organic acid profiles in feces of pigs with pathogenic or non-pathogenic diarrhea.	2001-12	11789618
Diagnoses and treatments in health-classified fattening herds rearing pigs all in-all out.	2001	11887397
Interaction of fluoroquinolones and certain ionophores in broilers: effect on blood levels and hepatic cytochrome p450 monooxygenase activity.	2001	11791885

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 `Mon Mar 31 18:06:56 GMT 2025` Edited by `admin` on `Mon Mar 31 18:06:56 GMT 2025`
Record UNII	3DX3XEK1BN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENROFLOXACIN

Official Name

English

ENROFLOXACIN FOR VETERINARY USE

Preferred 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

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