U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ENROFLOXACIN

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
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

Curator's Comment: Enrofloxacin crosses the blood-brain barrier in dogs and may cause CNS stimulation

Originator

Curator's Comment: Enrofloxacin was synthesized by Bayer researchers Grohe and Peterson in 1980 # Bayer

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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

PubMed

TitleDatePubMed
Mutant prevention concentration as a measure of fluoroquinolone potency against mycobacteria.
2000 Dec
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.
2000 Oct
Interaction of fluoroquinolones and certain ionophores in broilers: effect on blood levels and hepatic cytochrome p450 monooxygenase activity.
2001
Antibacterial drugs prescribed for dogs and cats in Sweden and Norway 1990-1998.
2001
Characterisation of some Ornithobacterium rhinotracheale strains and examination of their transmission via eggs.
2001
Antimicrobial susceptibility of intestinal bacteria from Swiss poultry flocks before the ban of antimicrobial growth promoters.
2001 Apr
Hypoadrenocorticism in a cat.
2001 Apr
Diagnosis and treatment of conjunctivitis in house finches associated with mycoplasmosis in Minnesota.
2001 Apr
Determination of fluoroquinolones in serum using an on-line clean-up column coupled to high-performance immunoaffinity-reversed-phase liquid chromatography.
2001 Apr 15
Effects of the matrix and sample preparation on the determination of fluoroquinolone residues in animal tissues.
2001 Apr 20
Monitoring Mycoplasma gallisepticum and Mycoplasma synoviae infection in breeder chickens after treatment with enrofloxacin.
2001 Apr-Jun
Determination of residues of enrofloxacin and its metabolite ciprofloxacin in biological materials by capillary electrophoresis.
2001 Aug 5
Organic acid profiles in feces of pigs with pathogenic or non-pathogenic diarrhea.
2001 Dec
Epidemiological studies of human and animal Salmonella typhimurium DT104 and DT104b isolates in Ireland.
2001 Feb
Effects of enrofloxacin and magnesium deficiency on matrix metabolism in equine articular cartilage.
2001 Feb
Nonenteric Escherichia coli isolates from dogs: 674 cases (1990-1998).
2001 Feb 1
Pharmacokinetics of enrofloxacin after intravenous and intramuscular administration in Angora goats.
2001 Jan
Effect of enrofloxacin-Na against pathogens related to the respiratory and alimentary diseases in suckling and weanling piglets.
2001 Jan
Non-bioequivalence of various trademarks of enrofloxacin and Baytril in cows.
2001 Jul
Activity and postantibiotic effect of marbofloxacin, enrofloxacin, difloxacin and ciprofloxacin against feline Bordetella bronchiseptica isolates.
2001 Jul 3
The use of antibiotics critical to human medicine in food-producing animals in Taiwan.
2001 Jun
Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998.
2001 Mar
Development of an indirect competitive ELISA for ciprofloxacin residues in food animal edible tissues.
2001 Mar
In vitro evidence for effects of magnesium supplementation on quinolone-treated horse and dog chondrocytes.
2001 Mar
Addressing the use of fluoroquinolone antibiotics in agriculture.
2001 Mar
Characterization of high-level fluoroquinolone resistance in Escherichia coli O78:K80 isolated from turkeys.
2001 Mar
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
Serogroups and antimicrobial susceptibility among Escherichia coli isolated from farmed mink (Mustela vison Schreiber) in Denmark.
2001 Mar 20
Inhibition tests for detection and presumptive identification of tetracyclines, beta-lactam antibiotics and quinolones in poultry meat.
2001 May
Effects of enrofloxacin and ciprofloxacin hydrochloride on canine and equine chondrocytes in culture.
2001 May
In vitro susceptibility to 15 antibiotics of vibrios isolated from penaeid shrimps in Northwestern Mexico.
2001 May
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
Antimicrobial susceptibility of Pasteurella multocida isolated from cattle and pigs.
2001 Sep
Antimicrobial susceptibility of udder pathogens isolated from dairy herds in the west littoral region of Uruguay.
2002
Biofilm bacteria: formation and comparative susceptibility to antibiotics.
2002 Apr
Questions study on Escherichia coli susceptibility.
2002 Apr 15
Idiosyncratic reaction to enrofloxacin in cats.
2002 Apr 27
In vitro development of resistance to enrofloxacin, erythromycin, tylosin, tiamulin and oxytetracycline in Mycoplasma gallisepticum, Mycoplasma iowae and Mycoplasma synoviae.
2002 Aug 2
Comparative serum pharmacokinetics of the fluoroquinolones enrofloxacin, difloxacin, marbofloxacin, and orbifloxacin in dogs after single oral administration.
2002 Feb
Using nonaqueous capillary electrophoresis to analyze several quinolones in pig kidney samples.
2002 Feb
Elimination of mycoplasma from leukemia-lymphoma cell lines using antibiotics.
2002 Feb
Monoclonal-based enzyme-linked immunosorbent assay and immunochromatographic assay for enrofloxacin in biological matrices.
2002 Jan
Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae.
2002 Jan
Susceptibility of human isolates of Salmonella typhimurium DT 104 to antimicrobial agents used in human and veterinary medicine.
2002 Jan
Spectrophotometric determination of ciprofloxacin, enrofloxacin and pefloxacin through charge transfer complex formation.
2002 Jan 1
Enrofloxacin resistance in Escherichia coli isolated from dogs with urinary tract infections.
2002 Jan 15
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
Pharmacokinetics after intravenous and oral administration of enrofloxacin in sheep.
2002 Jul
Antimicrobial susceptibility of Actinobacillus pleuropneumoniae, Escherichia coli, and Salmonella choleraesuis recovered from Taiwanese swine.
2002 Mar
Bayer seeks veterinary, industry backing before Baytril hearing.
2002 May 15
Patents

Patents

Sample Use Guides

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
  • Download
Name Type Language
ENROFLOXACIN
GREEN BOOK   HSDB   INN   MART.   MI   USAN   USP   USP-RS  
INN   USAN  
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
EP  
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
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
CFR 21 CFR 556.226
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
CFR 21 CFR 520.812
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
CFR 21 CFR 524.802
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
NCI_THESAURUS C795
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
CFR 21 CFR 522.812
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
Code System Code Type Description
WIKIPEDIA
Enrofloxacin
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
PUBCHEM
71188
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
FDA UNII
3DX3XEK1BN
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
RXCUI
24192
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY RxNorm
SMS_ID
300000023676
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
NCI_THESAURUS
C72660
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
NSC
758616
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
INN
5963
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
USAN
Z-54
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
HSDB
6952
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID1045619
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
CAS
93106-60-6
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
ChEMBL
CHEMBL15511
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
DRUG BANK
DB11404
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
MESH
C052904
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
MERCK INDEX
M4916
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY Merck Index
DAILYMED
3DX3XEK1BN
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
RS_ITEM_NUM
1235900
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
CHEBI
35720
Created by admin on Wed Jul 05 23:12:38 UTC 2023 , Edited by admin on Wed Jul 05 23:12:38 UTC 2023
PRIMARY
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