MARBOFLOXACIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H19FN4O4
Molecular Weight	362.3562
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCN(CC1)c2c(cc3c4c2OCN(C)n4cc(c3=O)C(=O)O)F

InChI

InChIKey=BPFYOAJNDMUVBL-UHFFFAOYSA-N

InChI=1S/C17H19FN4O4/c1-19-3-5-21(6-4-19)14-12(18)7-10-13-16(14)26-9-20(2)22(13)8-11(15(10)23)17(24)25/h7-8H,3-6,9H2,1-2H3,(H,24,25)

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/spl/data/25f0d2f2-83c0-45e0-9d13-7b351fc0df63/25f0d2f2-83c0-45e0-9d13-7b351fc0df63.xml#DI
Curator's Comment:: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=05196313-2371-45ad-a6fb-6269f8ef94c5

Marbofloxacin is an anti-bacterial veterinary medication which is approved by FDA and EMEA for the treatment of bacterial diseases in dogs and cats. The drug exerts its action by inhibiting bacterial DNA gyrase.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Skin infections 53 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm117196.pdf	Curative	Approved 7998	Zeniquin Approved Use Zeniquin (marbofloxacin) tablets are indicated for the treatment of infections in dogs associated with bacteria susceptible to marbofloxacin. Launch Date 932601600000
Soft tissue infections 3 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm117196.pdf	Curative	Approved 7998	Zeniquin Approved Use Zeniquin (marbofloxacin) tablets are indicated for the treatment of infections in dogs associated with bacteria susceptible to marbofloxacin. Launch Date 932601600000
Urinary tract infections (cystitis) 2 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm117196.pdf	Curative	Approved 7998	Zeniquin Approved Use Zeniquin (marbofloxacin) tablets are indicated for the treatment of infections in dogs associated with bacteria susceptible to marbofloxacin. Launch Date 932601600000

PubMed

Title	Date	PubMed
Pharmacokinetics, urinary excretion and dosage regimen of levofloxacin following a single intramuscular administration in cross bred calves.	2006 Dec	17106223
Clinical efficacy of intravenous administration of marbofloxacin in a Staphylococcus aureus infection in tissue cages in ponies.	2006 Dec	17083460
Determination of fluoroquinolones in milk samples by postcolumn derivatization liquid chromatography with luminescence detection.	2006 Dec 27	17177486
Pharmacokinetics of marbofloxacin in blue and gold macaws (Ara ararauna).	2006 Jun	16740085
Preliminary single-dose pharmacokinetics of marbofloxacin in ball pythons (Python regius).	2006 Mar	17312805
Multiresidue method for the determination of quinolone antibiotics in bovine raw milk by capillary electrophoresis-tandem mass spectrometry.	2006 Nov 15	17105157
Comparison of pharmacodynamic and pharmacokinetic indices of efficacy for 5 fluoroquinolones toward pathogens of dogs and cats.	2006 Nov-Dec	17186841
Mucosal permeability of water-soluble drugs in the equine jejunum: a preliminary investigation.	2006 Oct	16958782
Enrofloxacin and marbofloxacin in horses: comparison of pharmacokinetic parameters, use of urinary and metabolite data to estimate first-pass effect and absorbed fraction.	2006 Oct	16958777
Effect of chronic FIV infection, and efficacy of marbofloxacin treatment, on Mycoplasma haemofelis infection.	2006 Oct 31	16876338
Field evaluation of the efficacy of tolfenamic acid administered in one single preoperative injection for the prevention of postoperative pain in the dog.	2007 Dec	17991217
Naïve averaged, naïve pooled, and population pharmacokinetics of orally administered marbofloxacin in juvenile harbor seals.	2007 Feb 1	17269873
[Determination of 16 quinolone residues in animal tissues using high performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry].	2007 Jul	17970104
Pharmacokinetics of a single intravenous dose of marbofloxacin in adult donkeys.	2007 Jul 28	17660467
In vitro antimicrobial activity of marbofloxacin and enrofloxacin against bacterial strains isolated from companion animals.	2007 Jun	17645036
Separation of fifteen quinolones by high performance liquid chromatography: application to pharmaceuticals and ofloxacin determination in urine.	2007 Jun	17623463
Identification and comparison of marbofloxacin metabolites from the plasma of ball pythons (Python regius) and blue and gold macaws (Ara ararauna).	2007 Jun	17472658
Comparative pharmacokinetics of marbofloxacin in healthy and Mannheimia haemolytica infected calves.	2007 Jun	17118414
Microbiological detection of 10 quinolone antibiotic residues and its application to artificially contaminated poultry samples.	2007 Mar	17364926
Stability of frozen stock solutions of beta-lactam antibiotics, cephalosporins, tetracyclines and quinolones used in antibiotic residue screening and antibiotic susceptibility testing.	2007 Mar 14	17386725
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
Single-dose pharmacokinetics of marbofloxacin in Egyptian buffalo (Bubalus bubalis L.) steers.	2007 May-Jun	17555042
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
Susceptibility of Pseudomonas isolates from the ears and skin of dogs to enrofloxacin, marbofloxacin, and ciprofloxacin.	2007 Nov-Dec	17975216
Antimicrobial testing of selected fluoroquinolones against Pseudomonas aeruginosa isolated from canine otitis.	2007 Nov-Dec	17975212
Allometric scaling of marbofloxacin, moxifloxacin, danofloxacin and difloxacin pharmacokinetics: a retrospective analysis.	2007 Oct	17803728
Pharmacokinetic behavior and pharmacokinetic/pharmacodynamic integration of marbofloxacin after subcutaneous administration in goats.	2007 Sep	16807010
Comparative quantification of the in vitro activity of veterinary fluoroquinolones.	2007 Sep 20	17498893
Pulmonary function and antimicrobial concentration after marbofloxacin inhalation in horses.	2007 Sep 8	17827476
Improved determination of quinolones in milk at their MRL levels using LC-UV, LC-FD, LC-MS and LC-MS/MS and validation in line with regulation 2002/657/EC.	2008 Apr 14	18374707
Comprehensive screening and quantification of veterinary drugs in milk using UPLC-ToF-MS.	2008 Jul	18491081
Development of an immunochromatography strip for the rapid detection of 12 fluoroquinolones in chicken muscle and liver.	2008 Jul 23	18558699
[Multiresidue determination of quinolones in animal and fishery products by HPLC].	2008 Jun	18633210
Intraocular pharmacokinetics of intravenously administered marbofloxacin in rabbits with experimentally induced acute endophthalmitis.	2008 Mar	18312141
Marbofloxacin for the treatment of experimentally induced Mycoplasma haemofelis infection in cats.	2008 Mar-Apr	18312555
In-line solid-phase extraction preconcentration in capillary electrophoresis-tandem mass spectrometry for the multiresidue detection of quinolones in meat by pressurized liquid extraction.	2008 May	18409156
Efficacy of different treatment regimens of marbofloxacin in canine visceral leishmaniosis: a pilot study.	2008 May 31	18337012
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
Tissue distribution of marbofloxacin after 'systemic' administration into the isolated perfused bovine udder.	2008 Oct	17719251
Antimicrobial resistance and genetic characterization of fluoroquinolone resistance of Pseudomonas aeruginosa isolated from canine infections.	2008 Sep 18	18395369
Influence of systemic fluoroquinolone administration on the presence of Pasteurella multocida in the upper respiratory tract of clinically healthy calves.	2008 Sep 22	18808692
Single- and multiple-dose pharmacokinetics of marbofloxacin after oral administration to rabbits.	2009 Apr	19335109
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
Water-compatible molecularly imprinted polymer for the selective recognition of fluoroquinolone antibiotics in biological samples.	2009 Jan	18839153
Resolution of tongue lesions caused by Leishmania infantum in a dog treated with the association miltefosine-allopurinol.	2009 Mar 26	19426445
Pharmacokinetics of marbofloxacin after a single oral dose to loggerhead sea turtles (Caretta caretta).	2009 Oct	19375138
Pharmacokinetic and pharmacodynamic modelling of marbofloxacin administered alone and in combination with tolfenamic acid in goats.	2010 May	19299172

Patents

Sample Use Guides

In Vivo Use Guide

1.25 mg per pound (/lb) of body weight once daily, but may be increased to 2.5 mg/lb of body weight once daily.

Route of Administration: Other

In Vitro Use Guide

MIC50 values of marbofloxacin against pathogens isolated from skin, soft tissue and urinary tract infections in dogs were: Staphylococcus intermedius - 0.25 ug/ml, Escherichia coli - 0.03 ug/ml, Proteus mirabilis - 0.06 ug/ml, Beta-hemolytic Streptococcus, (not Group A or Group B) - 1 ug/ml, Streptococcus, Group D enterococcus - 1 ug/ml, Pasteurella multocida - 0.015 ug/ml, Staphylococcus aureus - 0.25 ug/ml, Enterococcus faecalis - 2 ug/ml, Klebsiella pneumoniae - 0.06 ug/ml.

Name

Type

Language

MARBOFLOXACIN

Official Name

English

9-FLUORO-2,3-DIHYDRO-3-METHYL-10-(4-METHYL-1-PIPERAZINYL)-7-OXO-7H-PYRIDO(3,2,1-IJ)(4,1,2)BENZOXADIAZINE-6-CARBOXYLIC ACID

Systematic Name

English

MARBOFLOXACIN [GREEN BOOK]

Common Name

English

MARBOFLOXACIN [MART.]

Common Name

English

MARBOFLOXACIN [INN]

Common Name

English

MARBOFLOXACIN [MI]

Common Name

English

RO 09-1168

Code

English

MARBOCYL

Brand Name

English

Classification Tree Code System Code

CFR

21 CFR 520.1310