Orbifloxacin

Basic Info

Common NameOrbifloxacin(F05749)
2D Structure
FRCD IDF05749
CAS Number113617-63-3
PubChem CID60605
FormulaC19H20F3N3O3
IUPAC Name

1-cyclopropyl-7-[(3S,5R)-3,5-dimethylpiperazin-1-yl]-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid

InChI Key

QIPQASLPWJVQMH-DTORHVGOSA-N

InChI

InChI=1S/C19H20F3N3O3/c1-8-5-24(6-9(2)23-8)17-14(21)13(20)12-16(15(17)22)25(10-3-4-10)7-11(18(12)26)19(27)28/h7-10,23H,3-6H2,1-2H3,(H,27,28)/t8-,9+

Canonical SMILES

CC1CN(CC(N1)C)C2=C(C3=C(C(=C2F)F)C(=O)C(=CN3C4CC4)C(=O)O)F

Isomeric SMILES

C[C@@H]1CN(C[C@@H](N1)C)C2=C(C3=C(C(=C2F)F)C(=O)C(=CN3C4CC4)C(=O)O)F

Synonyms
        
            1-cyclopropyl-7-((3S,5R)-3,5-dimethylpiperazin-1-yl)-5,6,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
        
            ORBIFLOXACIN
        
            113617-63-3
        
            Orbax
        
            UNII-660932TPY6
        
            660932TPY6
        
            NCGC00160518-01
        
            DSSTox_CID_26201
        
            DSSTox_RID_81432
        
            DSSTox_GSID_46201
Classifies
                

                  
                    Predicted: Veterinary Drug
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 - Dialkylarylamine - Tertiary aliphatic/aromatic amine - Benzenoid - Aryl fluoride - Pyridine - Aryl halide - Piperazine - 1,4-diazinane - Vinylogous amide - Vinylogous halide - Heteroaromatic compound - Tertiary amine - Amino acid - Amino acid or derivatives - Azacycle - Secondary amine - Carboxylic acid derivative - Carboxylic acid - Secondary aliphatic amine - Monocarboxylic acid or derivatives - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Amine - Organohalogen compound - Organofluoride - Organonitrogen compound - 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 Weight395.382
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Complexity691
Monoisotopic Mass395.146
Exact Mass395.146
XLogP0.9
Formal Charge0
Heavy Atom Count28
Defined Atom Stereocenter Count2
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-0.9767
Human Intestinal AbsorptionHIA+0.9824
Caco-2 PermeabilityCaco2+0.8335
P-glycoprotein SubstrateSubstrate0.8147
P-glycoprotein InhibitorNon-inhibitor0.8774
Non-inhibitor0.8229
Renal Organic Cation TransporterNon-inhibitor0.8090
Distribution
Subcellular localizationLysosome0.6023
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8430
CYP450 2D6 SubstrateNon-substrate0.8884
CYP450 3A4 SubstrateNon-substrate0.6356
CYP450 1A2 InhibitorNon-inhibitor0.8199
CYP450 2C9 InhibitorNon-inhibitor0.8246
CYP450 2D6 InhibitorNon-inhibitor0.9001
CYP450 2C19 InhibitorNon-inhibitor0.8252
CYP450 3A4 InhibitorNon-inhibitor0.8325
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6425
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9433
Non-inhibitor0.7847
AMES ToxicityAMES toxic0.6221
CarcinogensNon-carcinogens0.8088
Fish ToxicityHigh FHMT0.9931
Tetrahymena Pyriformis ToxicityHigh TPT0.9316
Honey Bee ToxicityLow HBT0.8932
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7770
Carcinogenicity (Three-class)Non-required0.5540
Model Value Unit
Absorption
Aqueous solubility-3.6133LogS
Caco-2 Permeability1.1068LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.9492LD50, mol/kg
Fish Toxicity1.3069pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5740pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MilkJapan0.02ppm
Pig,Edible OffalJapan0.02ppm
Cattle,Edible OffalJapan0.02ppm
Pig,KidneyJapan0.02ppm
Cattle,KidneyJapan0.02ppm
Pig,LiverJapan0.02ppm
Cattle,LiverJapan0.02ppm
Pig,FatJapan0.02ppm
Cattle,FatJapan0.02ppm
Pig,MuscleJapan0.02ppm
Cattle,MuscleJapan0.02ppm

References

TitleJournalDatePubmed ID
Development of a novel genetically modified bioluminescent-bacteria-based assayfor detection of fluoroquinolones in animal-derived foods.Anal Bioanal Chem2014 Dec25354889
Mixed immunoassay design for multiple chemical residues detection.Anal Bioanal Chem2013 Apr23380954
Amino acid substitutions in GyrA and ParC are associated with fluoroquinoloneresistance in Mycoplasma bovis isolates from Japanese dairy calves.J Vet Med Sci201323503166
Rapid screening method for quinolone residues in livestock and fishery productsusing immobilised metal chelate affinity chromatographic clean-up and liquidchromatography-fluorescence detection.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2011Sep21749230
Pharmacokinetic-pharmacodynamic integration of orbifloxacin in Japanese quail(Coturnix japonica) following oral and intravenous administration.J Vet Pharmacol Ther2011 Aug20950349
Quantitation of fluoroquinolones in honey using tandem mass spectrometry(LC-MS/MS): nested validation with two mass spectrometers.J AOAC Int2010 Sep-Oct21140677
Short communication: Fluoroquinolone susceptibility of Staphylococcus aureusstrains isolated from caprine clinical mastitis in southeast Spain.J Dairy Sci2010 Nov20965339
Rapid determination of fluoroquinolone residues in honey by a microbiologicalscreening method and liquid chromatography.J AOAC Int2010 Jul-Aug20922969
Single-step extraction followed by LC for determination of (fluoro)quinolone drugresidues in muscle, eggs, and milk.J Sep Sci2010 Apr20175091
Approaches for application of sub and supercritical fluid extraction forquantification of orbifloxacin from plasma and milk: application to dispositionkinetics.Anal Chim Acta2009 Jan 519046687
Pharmacokinetics and milk distribution characteristics of orbifloxacin following intravenous and intramuscular injection in lactating ewes.J Vet Pharmacol Ther2009 Aug19614838
Pharmacokinetics and milk penetration of orbifloxacin after intravenous,subcutaneous, and intramuscular administration to lactating goats.J Dairy Sci2007 Sep17699040
[Determination of 16 quinolone residues in animal tissues using high performance liquid chromatography coupled with electrospray ionization tandem massspectrometry].Se Pu2007 Jul17970104
Multiresidue determination of fluoroquinolones in shrimp by liquidchromatography-fluorescence-mass spectrometry.J AOAC Int2005 Jul-Aug16152936