DIFLOXACIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H19F2N3O3
Molecular Weight	399.3907
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCN(CC1)C2=CC3=C(C=C2F)C(=O)C(=CN3C4=CC=C(F)C=C4)C(O)=O

InChI

InChIKey=NOCJXYPHIIZEHN-UHFFFAOYSA-N

InChI=1S/C21H19F2N3O3/c1-24-6-8-25(9-7-24)19-11-18-15(10-17(19)23)20(27)16(21(28)29)12-26(18)14-4-2-13(22)3-5-14/h2-5,10-12H,6-9H2,1H3,(H,28,29)

HIDE SMILES / InChI

Description
Sources: https://web.archive.org/web/20171115071928/https://www.fda.gov/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm117107.htm
Curator's Comment: Description was created based on several sources, including http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500013811.pdf | https://www.ncbi.nlm.nih.gov/pubmed/2680058

Difloxacin is an aryl fluoroquinolone derivative. The primary bacterial target of fluoroquinolones is the enzyme deoxyribonucleic acid gyrase. Difloxacin is very potent against a broad spectrum of bacteria including aerobic ana anaerobic gram-positive and gram-negative oragnisms. DICURAL® (difloxacin hydrochloride) TABLETS are indicated for the management of diseases in dogs associated with bacteria susceptible to difloxacin.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2680058 \| http://www.kegg.jp/entry/D07828 \| http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500013811.pdf	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Activity of ciprofloxacin and other fluorinated quinolones against mycobacteria.	1987 Apr 27	3107379
In vitro susceptibilities of Mycobacterium tuberculosis to 10 antimicrobial agents.	1988 Sep	3143305
Comparative antimycobacterial activities of difloxacin, temafloxacin, enoxacin, pefloxacin, reference fluoroquinolones, and a new macrolide, clarithromycin.	1989 Apr	2524998
In vitro and in vivo activities of clarithromycin against Mycobacterium avium.	1989 Sep	2530933
Comparison of in vitro antimicrobial susceptibilities of Mycobacterium avium-M. intracellulare strains from patients with acquired immunodeficiency syndrome (AIDS), patients without AIDS, and animal sources.	1990 Jul	2386370
Comparative in-vitro activities of ten fluoroquinolones and fusidic acid against Mycobacterium spp.	1990 Sep	2228828
In-vitro activities of quinolones against mycobacteria.	1993 Dec	8144420
Spectrofluorometric determination of certain quinolone antibacterials using metal chelation.	2003 Jul 27	18969129
Sensitive luminescent determination of DNA using the terbium(III)-difloxacin complex.	2007 Feb 19	17386613
Microbiological detection of 10 quinolone antibiotic residues and its application to artificially contaminated poultry samples.	2007 Mar	17364926
Simultaneous multiresidue determination of tetracyclines and fluoroquinolones in catfish muscle using high performance liquid chromatography with fluorescence detection.	2007 Mar 14	17386722
Dual biosensor immunoassay-directed identification of fluoroquinolones in chicken muscle by liquid chromatography electrospray time-of-flight mass spectrometry.	2007 Mar 14	17386721
Simultaneous determination of trace levels of 10 quinolones in swine, chicken, and shrimp muscle tissues using HPLC with programmable fluorescence detection.	2007 May 16	17429982
Comparative activity of pradofloxacin against anaerobic bacteria isolated from dogs and cats.	2007 Nov	17872918
Multiresidue method for simultaneous determination of quinolone antibacterials in pig kidney samples by liquid chromatography with fluorescence detection.	2007 Nov 15	17951118
Pharmacokinetics after intravenous, intramuscular and subcutaneous administration of difloxacin in sheep.	2007 Oct	17343888
Ionic liquids as mobile phase additives for the high-performance liquid chromatographic analysis of fluoroquinolone antibiotics in water samples.	2008 Dec	18854988
Trace analysis of quinolone and fluoroquinolone antibiotics from wastewaters by liquid chromatography-electrospray tandem mass spectrometry.	2008 Dec 19	19007934
Multiresidue determination of quinolones in animal and fishery products by HPLC.	2008 Jun	18633210
Simultaneous determination of quinolone antibacterials in bovine milk by liquid chromatography-mass spectrometry.	2008 Nov	18651586
Simultaneous determination of 13 quinolones in eggs using column high-performance liquid chromatography/electrospray ionization-tandem mass spectrometry and depletion of pefloxacin methanesulfonate in eggs.	2008 Nov-Dec	19202815
Simultaneous determination of seven fluoroquinolones in royal jelly by ultrasonic-assisted extraction and liquid chromatography with fluorescence detection.	2009 Apr	19306254
Are liquid chromatography/electrospray tandem quadrupole fragmentation ratios unequivocal confirmation criteria?	2009 Apr	19241450
Fully automatic sample treatment by integration of microextraction by packed sorbents into commercial capillary electrophoresis-mass spectrometry equipment: application to the determination of fluoroquinolones in urine.	2009 Apr 15	19284777
[Simultaneous determination of 19 quinolone residues in honey using high performance liquid chromatography-tandem mass spectrometry].	2009 Jan	19449537
Rapid method for the determination and confirmation of fluoroquinolone residues in catfish using liquid chromatography/fluorescence detection and liquid chromatography-tandem mass spectrometry.	2009 Jul-Aug	19714995
Application of ionic liquids in high performance reversed-phase chromatography.	2009 Jun 4	19582220
Rapid determination of 19 quinolone residues in spiked fish and pig muscle by high-performance liquid chromatography (HPLC) tandem mass spectrometry.	2009 Mar	19680903
Simultaneous determination of eleven quinolones in animal feed by liquid chromatography with fluorescence and ultraviolet absorbance detection.	2009 Nov 13	19616214
Photolysis of difloxacin and sarafloxacin in aqueous systems.	2009 Oct	19751946
Microbial screening methods for detection of antibiotic residues in slaughter animals.	2009 Oct	19484227
In vitro residual anti-bacterial activity of difloxacin, sarafloxacin and their photoproducts after photolysis in water.	2009 Oct	19473738
Fluoroquinolone antibiotic determination in bovine, ovine and caprine milk using solid-phase extraction and high-performance liquid chromatography-fluorescence detection with ionic liquids as mobile phase additives.	2009 Oct 23	19268960
Quantification of danofloxacin and difloxacin in chicken tissues in the presence of sarafloxacin as interference.	2009 Sep 9	19689131
Single-step extraction followed by LC for determination of (fluoro)quinolone drug residues in muscle, eggs, and milk.	2010 Apr	20175091
Aquatic photochemistry of fluoroquinolone antibiotics: kinetics, pathways, and multivariate effects of main water constituents.	2010 Apr 1	20205456
Selective sample pretreatment by molecularly imprinted polymer monolith for the analysis of fluoroquinolones from milk samples.	2010 Apr 2	20189184
Fully automated screening of veterinary drugs in milk by turbulent flow chromatography and tandem mass spectrometry.	2010 Aug	20379812
Room temperature ionic liquid-mediated molecularly imprinted polymer monolith for the selective recognition of quinolones in pork samples.	2010 Dec	21082676
Antibiotic Treatment of Dogs and Cats during Pregnancy.	2010 Dec 14	21253497
Simultaneous determination of quinolones for veterinary use by high-performance liquid chromatography with electrochemical detection.	2010 Feb 1	20042380
Comparison of several extraction techniques for multiclass analysis of veterinary drugs in eggs using ultra-high pressure liquid chromatography-tandem mass spectrometry.	2010 Feb 28	20113729
Pharmacokinetics and milk penetration of difloxacin after a long-acting formulation for subcutaneous administration to lactating goats.	2010 Jul	20630222
Simultaneous determination of quinolones in fish by liquid chromatography coupled with fluorescence detection: comparison of sub-2 microm particles and conventional C18 columns.	2010 Jul	20586060
Rapid determination of fluoroquinolone residues in honey by a microbiological screening method and liquid chromatography.	2010 Jul-Aug	20922969
Behaviour of (14)C-sulfadiazine and (14)C-difloxacin during manure storage.	2010 Mar 1	20022355
Effects of fish cytochromes P450 inducers and inhibitors on difloxacin N-demethylation in kidney of Chinese idle (Ctenopharyngodon idellus).	2010 May	21787603
Dispersive liquid-liquid microextraction combined with nonaqueous capillary electrophoresis for the determination of fluoroquinolone antibiotics in waters.	2010 Oct	20859952
Effects of fish CYP inducers on difloxacin N-demethylation in kidney cell of Chinese idle (Ctenopharyngodon idellus).	2010 Sep	19685219
Quantitation of fluoroquinolones in honey using tandem mass spectrometry (LC-MS/MS): nested validation with two mass spectrometers.	2010 Sep-Oct	21140677

Patents

Sample Use Guides

In Vivo Use Guide

The dose range of difloxacin in dogs is 5 to 10 mg/kg (2.3 to 4.6 mg/lb) once a day for 2-3 days beyond cessation of clinical signs to a maximum of 30 days. For chickens and turkeys, the proposed dosage corresponds to a daily dose 10 mg/kg per day of difloxacin for up to 5 days.

Route of Administration: Oral

In Vitro Use Guide

MIC50 values (µg/mL) of difloxacin for canine bacterial isolates range from 0.05 to 1.83

Name

Type

Language

DIFLOXACIN

Official Name

English

DIFLOXACIN [EMA EPAR VETERINARY]

Common Name

English

3-QUINOLINECARBOXYLIC ACID, 6-FLUORO-1-(4-FLUOROPHENYL) 1,4-DIHYDRO-7-(4-METHYL-1-PIPERAZINYL)-4-OXO-

Common Name

English

6-FLUORO-1-(P-FLUOROPHENYL)-1,4-DIHYDRO-7-(4-METHYL-1-PIPERAZINYL)-4-OXO-3-QUINOLINECARBOXYLIC ACID

Common Name

English

DIFLOXACIN [MI]

Common Name

English

PULSAFLOX

Brand Name

English

difloxacin [INN]

Common Name

English

DICURAL

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C795