Kanamycin

Basic Info

Common NameKanamycin(F05662)
2D Structure
FRCD IDF05662
CAS Number59-01-8
PubChem CID6032
FormulaC18H36N4O11
IUPAC Name

(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol

InChI Key

SBUJHOSQTJFQJX-NOAMYHISSA-N

InChI

InChI=1S/C18H36N4O11/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17/h4-18,23-29H,1-3,19-22H2/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-/m1/s1

Canonical SMILES

C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)O)O)OC3C(C(C(C(O3)CO)O)N)O)N

Isomeric SMILES

C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)N)O)N

Synonyms
        
            Kanamicina [Italian]
        
            kanamycin
        
            KANAMYCIN A
        
            Kanamycin Base
        
            Kanamycin sulfate
        
            59-01-8
        
            Kanamycine
        
            Kanamycinum
        
            Kanamicina
        
            KM (the Antibiotic)
Classifies
                

                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbohydrates and carbohydrate conjugates
Intermediate Tree NodesAminosaccharides - Aminoglycosides - Aminocyclitol glycosides - 2-deoxystreptamine aminoglycosides
Direct Parent4,6-disubstituted 2-deoxystreptamines
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
Substituents4,6-disubstituted 2-deoxystreptamine - Glycosyl compound - O-glycosyl compound - Aminocyclitol or derivatives - Cyclohexanol - Cyclohexylamine - Cyclitol or derivatives - Monosaccharide - Oxane - Cyclic alcohol - Secondary alcohol - 1,2-aminoalcohol - Polyol - Organoheterocyclic compound - Acetal - Oxacycle - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Primary aliphatic amine - Organonitrogen compound - Organic nitrogen compound - Amine - Primary alcohol - Primary amine - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as 4,6-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C6-positions.

Properties

Property NameProperty Value
Molecular Weight484.503
Hydrogen Bond Donor Count11
Hydrogen Bond Acceptor Count15
Rotatable Bond Count6
Complexity638
Monoisotopic Mass484.238
Exact Mass484.238
XLogP-6.9
Formal Charge0
Heavy Atom Count33
Defined Atom Stereocenter Count15
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-0.9815
Human Intestinal AbsorptionHIA-0.9351
Caco-2 PermeabilityCaco2-0.7545
P-glycoprotein SubstrateSubstrate0.5281
P-glycoprotein InhibitorNon-inhibitor0.7592
Non-inhibitor0.9040
Renal Organic Cation TransporterNon-inhibitor0.8353
Distribution
Subcellular localizationLysosome0.5648
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8325
CYP450 2D6 SubstrateNon-substrate0.8323
CYP450 3A4 SubstrateNon-substrate0.6719
CYP450 1A2 InhibitorNon-inhibitor0.9143
CYP450 2C9 InhibitorNon-inhibitor0.9259
CYP450 2D6 InhibitorNon-inhibitor0.9317
CYP450 2C19 InhibitorNon-inhibitor0.9150
CYP450 3A4 InhibitorNon-inhibitor0.9700
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9261
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9772
Non-inhibitor0.8151
AMES ToxicityNon AMES toxic0.7406
CarcinogensNon-carcinogens0.9488
Fish ToxicityLow FHMT0.8825
Tetrahymena Pyriformis ToxicityLow TPT0.7299
Honey Bee ToxicityLow HBT0.6660
BiodegradationNot ready biodegradable0.8490
Acute Oral ToxicityIV0.6476
Carcinogenicity (Three-class)Non-required0.6793
Model Value Unit
Absorption
Aqueous solubility-0.7149LogS
Caco-2 Permeability-0.4681LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.5431LD50, mol/kg
Fish Toxicity2.1432pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.1270pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Chicken,EggsJapan0.5ppm
Chicken,KidneyJapan0.5ppm
Chicken,Edible OffalJapan0.5ppm
Chicken,LiverJapan0.5ppm
Chicken,FatJapan0.1ppm
Chicken,MuscleJapan0.5ppm
MilkJapan0.4ppm
Other Terrestrial Mammals,Edible OffalJapan0.6ppm
Pig,Edible OffalJapan0.2ppm
Cattle,Edible OffalJapan0.04ppm
Other Terrestrial Mammals,KidneyJapan3ppm
Pig,KidneyJapan0.1ppm
Cattle,KidneyJapan0.04ppm
Other Terrestrial Mammals,LiverJapan0.6ppm
Pig,LiverJapan0.1ppm
Cattle,LiverJapan0.04ppm
Other Terrestrial Mammals,FatJapan0.1ppm
Pig,FatJapan0.1ppm
Cattle,FatJapan0.04ppm
Other Terrestrial Mammals,MuscleJapan0.1ppm

References

TitleJournalDatePubmed ID
Sensitivity enhancement of aminoglycosides in hydrophilic interaction liquidchromatography with tandem mass spectrometry by post-column addition of tracesodium acetate in methanol.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2018Jun29160759
Comparative Study on Antibiotic Resistance and DNA Profiles of Salmonellaenterica Serovar Typhimurium Isolated from Humans, Retail Foods, and theEnvironment in Shanghai, China.Foodborne Pathog Dis2018 May 929741928
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
Electrochemical aptasensor for multi-antibiotics detection based on endonuclease and exonuclease assisted dual recycling amplification strategy.Talanta2018 Mar 129310232
Characterization of multiple antibiotic resistance of culturable microorganismsand metagenomic analysis of total microbial diversity of marine fish sold inretail shops in Mumbai, India.Environ Sci Pollut Res Int2018 Mar29243150
The antibacterial activity of LI-F type peptide against methicillin-resistantStaphylococcus aureus (MRSA) in vitro and inhibition of infections in murinescalded epidermis.Appl Microbiol Biotechnol2018 Mar29372300
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
Phenotypical resistance correlation networks for 10 non-typhoidal Salmonellasubpopulations in an active antimicrobial surveillance programme.Epidemiol Infect2018 Jun29708083
Yersinia enterocolitica in a Brazilian pork production chain: Tracking ofcontamination routes, virulence and antimicrobial resistance.Int J Food Microbiol2018 Jul 229649750
Microbial occurrence and antibiotic resistance in ready-to-go food items.J Food Sci Technol2018 Jul30042576
[Determination of the role of Salmonella enterica plasmids in antibioticsusceptibility and Caenorhabditis elegans pathogenicity].Mikrobiyol Bul2018 Jan29642832
Prevalence, risk factors and antimicrobial susceptibility test of Staphylococcus aureus in Bovine cross breed mastitic milk in and around Asella town, Oromiaregional state, southern Ethiopia.Acta Trop2018 Jan28935553
Microfluidic electrophoretic non-enzymatic kanamycin assay making use of astirring bar functionalized with gold-labeled aptamer, of a fluorescent DNAprobe, and of signal amplification via hybridization chain reaction.Mikrochim Acta2018 Feb 1729594631
Tomatidine and analog FC04-100 possess bactericidal activities against Listeria, Bacillus and Staphylococcus spp.BMC Pharmacol Toxicol2018 Feb 1329439722
Prevalence and Molecular Characterization of Antimicrobial Resistance inEscherichia coli Isolated from Raw Milk and Raw Milk Cheese in Egypt.J Food Prot2018 Feb29323530
Antibiotic resistance of Aeromonas ssp. strains isolated from Sparus auratareared in Italian mariculture farms.Int J Food Microbiol2018 Aug 130081345
Case study on the soil antibiotic resistome in an urban community garden.Int J Antimicrob Agents2018 Aug29857032
Carbapenemases and Extended-Spectrum β-Lactamase-Producing Multidrug-ResistantEscherichia coli Isolated from Retail Chicken in Peshawar: First Report fromPakistan.J Food Prot2018 Aug30019956
Antimicrobial Resistance of Enterococcus Species Isolated from Chicken in Turkey.Korean J Food Sci Anim Resour2018 Apr29805287