Norfloxacin

Basic Info

Common NameNorfloxacin(F05918)
2D Structure
FRCD IDF05918
CAS Number70458-96-7
PubChem CID4539
FormulaC16H18FN3O3
IUPAC Name

1-ethyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid

InChI Key

OGJPXUAPXNRGGI-UHFFFAOYSA-N

InChI

InChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)

Canonical SMILES

CCN1C=C(C(=O)C2=CC(=C(C=C21)N3CCNCC3)F)C(=O)O

Isomeric SMILES

CCN1C=C(C(=O)C2=CC(=C(C=C21)N3CCNCC3)F)C(=O)O

Synonyms
        
            Baccidal
        
            norfloxacin
        
            70458-96-7
        
            Norfloxacine
        
            Noroxin
        
            Chibroxin
        
            Sebercim
        
            MK-366
        
            Norfloxacinum
        
            Norfloxacino
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 - Tertiary aliphatic/aromatic amine - Dialkylarylamine - Aryl fluoride - Aryl halide - 1,4-diazinane - Piperazine - Pyridine - Benzenoid - Vinylogous amide - Heteroaromatic compound - Amino acid or derivatives - Amino acid - Tertiary amine - Azacycle - Secondary amine - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Carboxylic acid - Secondary aliphatic amine - Amine - Organic oxygen compound - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Organohalogen compound - Organofluoride - Organonitrogen compound - Organooxygen 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 Weight319.336
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Complexity519
Monoisotopic Mass319.133
Exact Mass319.133
XLogP-1
Formal Charge0
Heavy Atom Count23
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-0.9824
Human Intestinal AbsorptionHIA+0.9916
Caco-2 PermeabilityCaco2-0.8683
P-glycoprotein SubstrateSubstrate0.8554
P-glycoprotein InhibitorNon-inhibitor0.8490
Non-inhibitor0.8657
Renal Organic Cation TransporterNon-inhibitor0.7588
Distribution
Subcellular localizationLysosome0.4392
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8301
CYP450 2D6 SubstrateNon-substrate0.9116
CYP450 3A4 SubstrateNon-substrate0.7558
CYP450 1A2 InhibitorNon-inhibitor0.9046
CYP450 2C9 InhibitorNon-inhibitor0.9268
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9148
CYP450 3A4 InhibitorNon-inhibitor0.8988
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5702
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7034
Non-inhibitor0.5292
AMES ToxicityAMES toxic0.9108
CarcinogensNon-carcinogens0.7923
Fish ToxicityHigh FHMT0.9968
Tetrahymena Pyriformis ToxicityHigh TPT0.9289
Honey Bee ToxicityLow HBT0.8969
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7846
Carcinogenicity (Three-class)Non-required0.6040
Model Value Unit
Absorption
Aqueous solubility-3.6659LogS
Caco-2 Permeability0.7124LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8785LD50, mol/kg
Fish Toxicity1.3230pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5348pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Poultry Animals,Edible OffalJapan0.1ppm
Chicken,Edible OffalJapan0.02ppm
Other Poultry Animals,KidneyJapan0.1ppm
Chicken,KidneyJapan0.02ppm
Other Poultry Animals,LiverJapan0.1ppm
Chicken,LiverJapan0.02ppm
Other Poultry Animals,FatJapan0.1ppm
Chicken,FatJapan0.02ppm
Other Poultry Animals,MuscleJapan0.1ppm
Chicken,MuscleJapan0.02ppm
Pig,Edible OffalJapan0.02ppm
Pig,KidneyJapan0.02ppm
Pig,LiverJapan0.02ppm
Pig,FatJapan0.02ppm
Pig,MuscleJapan0.02ppm

References

TitleJournalDatePubmed ID
Sorption of norfloxacin, sulfamerazine and oxytetracycline by KOH-modifiedbiochar under single and ternary systems.Bioresour Technol2018 Sep29763802
UPLC-MS/MS analysis of antibiotics in pharmaceutical effluent in Tunisia:ecotoxicological impact and multi-resistant bacteria dissemination.Arch Microbiol2018 May29230492
Presence of antibiotic residues in various environmental compartments of Shandongprovince in eastern China: Its potential for resistance development andecological and human risk.Environ Int2018 May29501851
Whole-Genome Sequencing and Genetic Analysis Reveal Novel Stress Responses toIndividual Constituents of Essential Oils in Escherichia coli.Appl Environ Microbiol2018 Mar 1929374037
Toxicological assessment of hospital wastewater in different treatment processes.Environ Sci Pollut Res Int2018 Mar26099595
Assessment of Antibiotic Susceptibility within Lactic Acid Bacteria andCoagulase-Negative Staphylococci Isolated from Hunan Smoked Pork, a NaturallyFermented Meat Product in China.J Food Sci2018 Jun29786847
An automated magnetic dispersive micro-solid phase extraction in a fluidizedreactor for the determination of fluoroquinolones in baby food samples.Anal Chim Acta2018 Feb 2529291807
Universal simultaneous multiplex ELISA of small molecules in milk based on dualluciferases.Anal Chim Acta2018 Feb 2529291795
Determination of 21 antibiotics in sea cucumber using accelerated solventextraction with in-cell clean-up coupled to ultra-performance liquidchromatography-tandem mass spectrometry.Food Chem2018 Aug 3029655759
Evaluation of probiotic attributes of Lactobacillus sp. isolated from cow andbuffalo curd samples collected from KandyCeylon Med J2017 Sep 3029076707
Bakery by-products based feeds borne-Saccharomyces cerevisiae strains with probiotic and antimycotoxin effects plus antibiotic resistance properties for use in animal production.Food Chem Toxicol2017 Sep28259658
Chemical, microbial and antibiotic susceptibility analyses of groundwater after amajor flood event in Chennai.Sci Data2017 Oct 1028994821
Quinolone Resistance Determinants of Clinical Salmonella Enteritidis in Thailand.Microb Drug Resist2017 Oct28437229
Molecular characterization of Escherichia coli recovered from traditional milkproducts in Kashan, Iran.Vet World2017 Oct29184374
Designation of pathogenic resistant bacteria in the Sparusaurata sea collected inTunisia coastlines: Correlation with high performance liquidchromatography-tandem mass spectrometry analysis of antibiotics.Microb Pathog2017 May28062288
Detection of antibiotics in chicken eggs obtained from supermarkets in Ho ChiMinh City, Vietnam.J Environ Sci Health B2017 Jun 328281880
Prevalence and Antimicrobial Resistance of Salmonella Isolates from ChickenCarcasses in Retail Markets in Yangon, Myanmar.J Food Prot2017 Jun28463083
Determination of norfloxacin in food by an enhanced spectrofluorimetric method.J Sci Food Agric2017 Jun27714818
Switchable hydrophilicity solvent membrane-based microextraction: HPLC-FLDdetermination of fluoroquinolones in shrimps.Anal Chim Acta2017 Jul 1128576316
Antimicrobial susceptibility and phylotyping profile of pathogenic Escherichiacoli and Salmonella enterica isolates from calves and pigs in Minas Gerais,Brazil.Trop Anim Health Prod2017 Jan27709395