Marbofloxacin

Basic Info

Common NameMarbofloxacin(F05645)
2D Structure
FRCD IDF05645
CAS Number115550-35-1
PubChem CID60651
FormulaC17H19FN4O4
IUPAC Name

None

InChI Key

BPFYOAJNDMUVBL-UHFFFAOYSA-N

InChI

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)

Canonical SMILES

CN1CCN(CC1)C2=C(C=C3C4=C2OCN(N4C=C(C3=O)C(=O)O)C)F

Isomeric SMILES

CN1CCN(CC1)C2=C(C=C3C4=C2OCN(N4C=C(C3=O)C(=O)O)C)F

Synonyms
        
            Marbofloxacine
        
            Marbofloxacin
        
            115550-35-1
        
            Zeniquin
        
            Marbocyl
        
            Marbofloxacine [INN-French]
        
            Marbofloxacinum [INN-Latin]
        
            Marbofloxacino [INN-Spanish]
        
            UNII-8X09WU898T
        
            BPFYOAJNDMUVBL-UHFFFAOYSA-N
Classifies
                

                  
                    Predicted: Plant Toxin
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassQuinolines and derivatives
SubclassQuinoline carboxylic acids
Intermediate Tree NodesNot available
Direct ParentQuinoline carboxylic acids
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsQuinoline-3-carboxylic acid - Fluoroquinolone - N-arylpiperazine - Aminoquinoline - Haloquinoline - Dihydroquinolone - Dihydroquinoline - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Tertiary aliphatic/aromatic amine - Dialkylarylamine - N-methylpiperazine - N-alkylpiperazine - 1,4-diazinane - Aryl halide - Aryl fluoride - Piperazine - Pyridine - Benzenoid - Heteroaromatic compound - Vinylogous amide - Amino acid or derivatives - Amino acid - Tertiary amine - Tertiary aliphatic amine - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Azacycle - Carboxylic acid - Oxacycle - Amine - Organopnictogen compound - Organic oxygen compound - Organic oxide - Organohalogen compound - Organofluoride - Organonitrogen compound - Organooxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Properties

Property NameProperty Value
Molecular Weight362.361
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count2
Complexity636
Monoisotopic Mass362.139
Exact Mass362.139
XLogP-0.5
Formal Charge0
Heavy Atom Count26
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9038
Human Intestinal AbsorptionHIA+0.9840
Caco-2 PermeabilityCaco2+0.6696
P-glycoprotein SubstrateSubstrate0.7128
P-glycoprotein InhibitorNon-inhibitor0.7311
Non-inhibitor0.7908
Renal Organic Cation TransporterNon-inhibitor0.7863
Distribution
Subcellular localizationLysosome0.4781
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8964
CYP450 2D6 SubstrateNon-substrate0.8564
CYP450 3A4 SubstrateSubstrate0.5141
CYP450 1A2 InhibitorNon-inhibitor0.9026
CYP450 2C9 InhibitorNon-inhibitor0.6635
CYP450 2D6 InhibitorNon-inhibitor0.9280
CYP450 2C19 InhibitorNon-inhibitor0.8104
CYP450 3A4 InhibitorNon-inhibitor0.7696
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7516
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8492
Non-inhibitor0.7841
AMES ToxicityAMES toxic0.9107
CarcinogensNon-carcinogens0.8054
Fish ToxicityHigh FHMT0.9976
Tetrahymena Pyriformis ToxicityHigh TPT0.9408
Honey Bee ToxicityLow HBT0.8944
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7245
Carcinogenicity (Three-class)Non-required0.6124
Model Value Unit
Absorption
Aqueous solubility-3.5251LogS
Caco-2 Permeability1.1188LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4016LD50, mol/kg
Fish Toxicity1.1461pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6464pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MilkJapan0.08ppm
Pig,Edible OffalJapan0.2ppm
Cattle,Edible OffalJapan0.2ppm
Pig,KidneyJapan0.2ppm
Cattle,KidneyJapan0.2ppm
Pig,LiverJapan0.2ppm
Cattle,LiverJapan0.2ppm
Pig,FatJapan0.05ppm
Cattle,FatJapan0.05ppm
Pig,MuscleJapan0.2ppm
Cattle,MuscleJapan0.2ppm

References

TitleJournalDatePubmed ID
Prevalence of most common human pathogenic Campylobacter spp. in dogs and cats inStyria, Austria.Vet Med Sci2018 May29851311
Efficacy of a one-shot marbofloxacin treatment on acute pleuropneumonia afterexperimental aerosol inoculation of nursery pigs.Porcine Health Manag2018 Jun 2229977591
Pharmacokinetics of marbofloxacin administered via intravenous regional limbperfusion in dairy cows: evaluation of two different tourniquets.Vet Rec Open2017 Sep 2629018533
Tissue distribution of marbofloxacin in pigs after a single intramuscularinjection.J Vet Sci2017 Jun 3027515270
Pharmacokinetics, milk penetration and PK/PD analysis by Monte Carlo simulationof marbofloxacin, after intravenous and intramuscular administration to lactatinggoats.J Vet Pharmacol Ther2017 Dec28470723
Efficient Reduction of Antibacterial Activity and Cytotoxicity of Fluoroquinolones by Fungal-Mediated N-Oxidation.J Agric Food Chem2017 Apr 1928365994
Determination of marbofloxacin in plasma and synovial fluid by ultrafiltrationfollowed by HPLC-MS/MS.J Pharm Biomed Anal2016 May 1026859613
A Liquid Chromatography-Tandem Mass Spectrometry Method for the Detection ofAntimicrobial Agents from Seven Classes in Calf Milk Replacers: Validation andApplication.J Agric Food Chem2016 Mar 3026971558
Use of micellar liquid chromatography to analyze oxolinic acid, flumequine,marbofloxacin and enrofloxacin in honey and validation according to the2002/657/EC decision.Food Chem2016 Jul 126920300
Wildlife contamination with fluoroquinolones from livestock: Widespreadoccurrence of enrofloxacin and marbofloxacin in vultures.Chemosphere2016 Feb26498102
Electrical field assisted matrix solid phase dispersion as a powerful tool toimprove the extraction efficiency and clean-up of fluoroquinolones in bovinemilk.J Chromatogr A2016 Aug 2627492598
Antibiotics and sweeteners in the aquatic environment: biodegradability,formation of phototransformation products, and in vitro toxicity.Environ Sci Pollut Res Int2015 Nov26169816
Microbial screening for quinolones residues in cow milk by bio-optical method.J Pharm Biomed Anal2015 Mar 1525555518
Using deconvolution to understand the mechanism for variable plasmaconcentration-time profiles after intramuscular injection.Int J Pharm2015 Mar 1525636300
Luminescent determination of quinolones in milk samples by liquidchromatography/post-column derivatization with terbium oxide nanoparticles.J Chromatogr A2015 Jul 3126077970
Multiresidue determination of fluoroquinolones in poultry muscle and kidneyaccording to the regulation 2002/657/EC. A systematic comparison of two differentapproaches: Liquid chromatography coupled to high-resolution mass spectrometry ortandem mass spectrometry.J Chromatogr A2015 Jan 3025577647
Determination of fluoroquinolones in chicken feces - a new liquid-liquidextraction method combined with LC-MS/MS.Environ Toxicol Pharmacol2014 Nov25305740
Comparison of different solid-phase extraction materials for the determination offluoroquinolones in chicken plasma by LC-MS/MS.J Chromatogr B Analyt Technol Biomed Life Sci2014 Mar 124566266
Development of a novel genetically modified bioluminescent-bacteria-based assayfor detection of fluoroquinolones in animal-derived foods.Anal Bioanal Chem2014 Dec25354889
Development of a highly sensitive and specific immunoassay for enrofloxacin basedon heterologous coating haptens.Anal Chim Acta2014 Apr 1124745749