Nalidixic Acid

Basic Info

Common NameNalidixic Acid(F06212)
2D Structure
FRCD IDF06212
CAS Number389-08-2
PubChem CID4421
FormulaC12H12N2O3
IUPAC Name

1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid

InChI Key

MHWLWQUZZRMNGJ-UHFFFAOYSA-N

InChI

InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)

Canonical SMILES

CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O

Isomeric SMILES

CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O

Synonyms
        
            nalidixic acid
        
            389-08-2
        
            Nalidixin
        
            Nevigramon
        
            Nalidixate
        
            Uronidix
        
            Innoxalon
        
            Nalidixan
        
            Nalitucsan
        
            Sicmylon
Classifies
                

                  
                    Predicted: Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassDiazanaphthalenes
SubclassNaphthyridines
Intermediate Tree NodesNot available
Direct ParentNaphthyridine carboxylic acids and derivatives
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsNaphthyridine carboxylic acid - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Methylpyridine - Pyridine - Heteroaromatic compound - Vinylogous amide - Azacycle - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Organic oxide - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. These are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group.

Properties

Property NameProperty Value
Molecular Weight232.239
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Complexity378
Monoisotopic Mass232.085
Exact Mass232.085
XLogP1.4
Formal Charge0
Heavy Atom Count17
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+0.8945
Human Intestinal AbsorptionHIA+0.9873
Caco-2 PermeabilityCaco2+0.6315
P-glycoprotein SubstrateNon-substrate0.5071
P-glycoprotein InhibitorNon-inhibitor0.8838
Non-inhibitor0.8566
Renal Organic Cation TransporterNon-inhibitor0.8104
Distribution
Subcellular localizationMitochondria0.8541
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7898
CYP450 2D6 SubstrateNon-substrate0.9116
CYP450 3A4 SubstrateNon-substrate0.7202
CYP450 1A2 InhibitorNon-inhibitor0.7888
CYP450 2C9 InhibitorNon-inhibitor0.8934
CYP450 2D6 InhibitorNon-inhibitor0.9115
CYP450 2C19 InhibitorNon-inhibitor0.7834
CYP450 3A4 InhibitorNon-inhibitor0.9531
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8555
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9392
Non-inhibitor0.8534
AMES ToxicityNon AMES toxic0.9133
CarcinogensNon-carcinogens0.8815
Fish ToxicityHigh FHMT0.5379
Tetrahymena Pyriformis ToxicityHigh TPT0.8927
Honey Bee ToxicityLow HBT0.7668
BiodegradationNot ready biodegradable0.8553
Acute Oral ToxicityIII0.7888
Carcinogenicity (Three-class)Warning0.5225
Model Value Unit
Absorption
Aqueous solubility-3.4326LogS
Caco-2 Permeability1.2722LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0874LD50, mol/kg
Fish Toxicity1.3219pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6157pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Cattle,Edible OffalJapan0.03ppm
Cattle,KidneyJapan0.03ppm
Cattle,LiverJapan0.03ppm
Cattle,FatJapan0.03ppm
Cattle,MuscleJapan0.03ppm

References

TitleJournalDatePubmed ID
Prevalence, bioserotyping and antibiotic resistance of pathogenic Yersiniaenterocolitica detected in pigs at slaughter in Sardinia.Int J Food Microbiol2018 Oct 2029929063
Emergence of mcr-1 plasmid-mediated colistin-resistant Escherichia coli isolates from seawater.Sci Total Environ2018 Nov 1529894885
Genetic Basis and Clonal Population Structure of Antibiotic Resistance inCampylobacter jejuni Isolated From Broiler Carcasses in Belgium.Front Microbiol2018 May 1729867900
Prevalence of most common human pathogenic Campylobacter spp. in dogs and cats inStyria, Austria.Vet Med Sci2018 May29851311
Whole-Genome Sequencing and Genetic Analysis Reveal Novel Stress Responses toIndividual Constituents of Essential Oils in Escherichia coli.Appl Environ Microbiol2018 Mar 1929374037
Studying the Phenotypic and Genotypic Expression of Antibiotic Resistance inCampylobacter jejuni under Stress Conditions.Bull Exp Biol Med2018 Mar29504101
Genetic relatedness, antimicrobial resistance and biofilm formation of Salmonellaisolated from naturally contaminated poultry and their processing environment in northern Malaysia.Food Res Int2018 Mar29433269
Molecular Analysis, Biochemical Characterization, Antimicrobial Activity, andImmunological Analysis of Proteus mirabilis Isolated from Broilers.J Food Sci2018 Mar29437227
Antimicrobial resistance, virulence genes and genetic relatedness of Salmonellaenterica serotype Enteritidis isolates recovered from human gastroenteritis inTehran, Iran.J Glob Antimicrob Resist2018 Mar29045813
Ciprofloxacin and nalidixic acid resistance of Salmonella spp. isolated fromretail food in Poland.Int J Food Microbiol2018 Jul 229649749
[Determination of the role of Salmonella enterica plasmids in antibioticsusceptibility and Caenorhabditis elegans pathogenicity].Mikrobiyol Bul2018 Jan29642832
Prevalence and Molecular Characterization of Antimicrobial Resistance inEscherichia coli Isolated from Raw Milk and Raw Milk Cheese in Egypt.J Food Prot2018 Feb29323530
Quantitative prevalence and characterization of Campylobacter from chicken andduck carcasses from poultry slaughterhouses in South Korea.Poult Sci2018 Aug 129757448
Use of whole-genome sequencing for Campylobacter surveillance from NARMS retailpoultry in the United States in 2015.Food Microbiol2018 Aug29526197
Antimicrobial Resistance of Thermotolerant Campylobacter Species Isolated fromHumans, Food-Producing Animals, and Products of Animal Origin: A WorldwideMeta-Analysis.Microb Drug Resist2018 Apr 3029708832
Antimicrobial resistance in clinical Escherichia coli isolates from poultry andlivestock, China.PLoS One2017 Sep 2128934348
Antimicrobial resistance in Escherichia coli and Salmonella spp. isolates fromfresh produce and the impact to food safety.J Environ Sci Health B2017 Sep 228679083
Phylogenetic Analysis and Antimicrobial Profiles of Cultured EmergingOpportunistic Pathogens (Phyla Actinobacteria and Proteobacteria) Identified inHot Springs.Int J Environ Res Public Health2017 Sep 1528914802
Microbial loads and antibiotic resistance patterns of Staphylococcus aureus indifferent types of raw poultry-based meat preparations.Poult Sci2017 Sep 129050434
Prevalence and risk factors for thermotolerant species of Campylobacter inpoultry meat at retail in Europe.Poult Sci2017 Sep 128854745