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
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
In-vitro activities of quinolones against mycobacteria.	1993 Dec	8144420
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
Activity and postantibiotic effect of marbofloxacin, enrofloxacin, difloxacin and ciprofloxacin against feline Bordetella bronchiseptica isolates.	2001 Jul 3	11356321
Using nonaqueous capillary electrophoresis to analyze several quinolones in pig kidney samples.	2002 Feb	11870754
Multiresidue determination of eleven quinolones in milk by liquid chromatography with fluorescence detection.	2005 Nov-Dec	16526452
Simultaneous determination of (fluoro)quinolone antibiotics in kidney, marine products, eggs, and muscle by enzyme-linked immunosorbent assay (ELISA).	2006 Apr 19	16608195
Determination of fluoroquinolones in chicken tissues by LC-coupled electrospray ionisation and atmospheric pressure chemical ionisation.	2006 Jan	16485718
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
Dual biosensor immunoassay-directed identification of fluoroquinolones in chicken muscle by liquid chromatography electrospray time-of-flight mass spectrometry.	2007 Mar 14	17386721
Pharmacokinetics after intravenous, intramuscular and subcutaneous administration of difloxacin in sheep.	2007 Oct	17343888
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
Are liquid chromatography/electrospray tandem quadrupole fragmentation ratios unequivocal confirmation criteria?	2009 Apr	19241450
Metabolism and excretion kinetics of 14C-labeled and non-labeled difloxacin in pigs after oral administration, and antimicrobial activity of manure containing difloxacin and its metabolites.	2009 Apr	19181312
Pharmacokinetics and intramuscular bioavailability of difloxacin in dromedary camels (Camelus dromedarius).	2009 Feb	18603456
Serovar distribution and antimicrobial susceptibility of swine Salmonella isolates from clinically ill pigs in diagnostic submissions from Indiana in the United States.	2009 Mar	19187513
Ultra performance liquid chromatography tandem mass spectrometry performance evaluation for analysis of antibiotics in natural waters.	2009 Mar	19148627
Photolysis of difloxacin and sarafloxacin in aqueous systems.	2009 Oct	19751946
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

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