Apramycin

Basic Info

Common NameApramycin(F05766)
2D Structure
FRCD IDF05766
CAS Number37321-09-8
PubChem CID3081545
FormulaC21H41N5O11
IUPAC Name

(2R,3R,4S,5S,6S)-2-[[(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-4-hydroxy-3-(methylamino)-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]oxy]-5-amino-6-(hydroxymethyl)oxane-3,4-diol

InChI Key

XZNUGFQTQHRASN-XQENGBIVSA-N

InChI

InChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1

Canonical SMILES

CNC1C(C2C(CC(C(O2)OC3C(CC(C(C3O)O)N)N)N)OC1OC4C(C(C(C(O4)CO)N)O)O)O

Isomeric SMILES

CN[C@H]1[C@H]([C@@H]2[C@H](C[C@H]([C@H](O2)O[C@@H]3[C@H](C[C@H]([C@@H]([C@H]3O)O)N)N)N)O[C@@H]1O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)N)O)O)O

Synonyms
        
            apramycin
        
            Nebramycin II
        
            37321-09-8
        
            Nebramycin factor 2
        
            Apramycinum
        
            Apramicina
        
            Apramycine
        
            UNII-388K3TR36Z
        
            Ambylan
        
            Apralan
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
Direct ParentAminocyclitol glycosides
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
SubstituentsAmino cyclitol glycoside - Hexose monosaccharide - Aminocyclitol or derivatives - Cyclohexylamine - Cyclohexanol - Oxane - Cyclitol or derivatives - Monosaccharide - 1,3-aminoalcohol - Cyclic alcohol - Secondary alcohol - 1,2-aminoalcohol - Oxacycle - Organoheterocyclic compound - Secondary amine - Acetal - Secondary aliphatic amine - Organopnictogen compound - Primary aliphatic amine - Organonitrogen compound - Primary alcohol - Organic nitrogen compound - Amine - Alcohol - Primary amine - Hydrocarbon derivative - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.

Properties

Property NameProperty Value
Molecular Weight539.583
Hydrogen Bond Donor Count11
Hydrogen Bond Acceptor Count16
Rotatable Bond Count6
Complexity760
Monoisotopic Mass539.28
Exact Mass539.28
XLogP-7
Formal Charge0
Heavy Atom Count37
Defined Atom Stereocenter Count17
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-0.9898
Human Intestinal AbsorptionHIA-0.8007
Caco-2 PermeabilityCaco2-0.7556
P-glycoprotein SubstrateSubstrate0.5680
P-glycoprotein InhibitorNon-inhibitor0.8164
Non-inhibitor0.9619
Renal Organic Cation TransporterNon-inhibitor0.8850
Distribution
Subcellular localizationLysosome0.4869
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7737
CYP450 2D6 SubstrateNon-substrate0.8285
CYP450 3A4 SubstrateNon-substrate0.5440
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9196
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9025
CYP450 3A4 InhibitorNon-inhibitor0.9234
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8708
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9812
Non-inhibitor0.8385
AMES ToxicityAMES toxic0.5193
CarcinogensNon-carcinogens0.9671
Fish ToxicityLow FHMT0.9003
Tetrahymena Pyriformis ToxicityHigh TPT0.5400
Honey Bee ToxicityLow HBT0.5720
BiodegradationNot ready biodegradable0.9023
Acute Oral ToxicityIII0.4674
Carcinogenicity (Three-class)Non-required0.6360
Model Value Unit
Absorption
Aqueous solubility-1.5700LogS
Caco-2 Permeability-0.6637LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2488LD50, mol/kg
Fish Toxicity1.8870pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.0245pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Poultry Animals,KidneyJapan0.8ppm
Chicken,KidneyJapan0.8ppm
Kidney Of SwineUnited States0.1ppm
Other Poultry Animals,Edible OffalJapan0.8ppm
Chicken,Edible OffalJapan0.8ppm
Other Poultry Animals,LiverJapan0.8ppm
Chicken,LiverJapan0.8ppm
Other Poultry Animals,FatJapan0.2ppm
Chicken,FatJapan0.2ppm
Other Poultry Animals,MuscleJapan0.2ppm
Chicken,MuscleJapan0.2ppm
Other Terrestrial Mammals,Edible OffalJapan2ppm
Pig,Edible OffalJapan0.06ppm
Cattle,Edible OffalJapan2ppm
Other Terrestrial Mammals,KidneyJapan2ppm
Pig,KidneyJapan0.06ppm
Cattle,KidneyJapan10ppm
Other Terrestrial Mammals,LiverJapan2ppm
Pig,LiverJapan0.06ppm
Other Terrestrial Mammals,FatJapan0.05ppm

References

TitleJournalDatePubmed ID
Characterization of Resistance Patterns and Detection of Apramycin ResistanceGenes in Escherichia coli Isolated from Chicken Feces and Houseflies afterApramycin Administration.Front Microbiol2018 Feb 2729535694
Complete sequence of a plasmid from a bovine methicillin-resistant Staphylococcusaureus harbouring a novel ica-like gene cluster in addition to antimicrobial and heavy metal resistance genes.Vet Microbiol2017 Feb27476981
Analysis of 76 veterinary pharmaceuticals from 13 classes includingaminoglycosides in bovine muscle by hydrophilic interaction liquidchromatography-tandem mass spectrometry.J Chromatogr A2016 Jun 2427215463
Apramycin treatment affects selection and spread of a multidrug-resistantEscherichia coli strain able to colonize the human gut in the intestinalmicrobiota of pigs.Vet Res2016 Jan 726739225
Presence of antimicrobial resistance in coliform bacteria from hatching broilereggs with emphasis on ESBL/AmpC-producing bacteria.Avian Pathol2016 Aug27011291
Class 1 and class 2 integrons in avian pathogenic Escherichia coli from poultryin Italy.Poult Sci2015 Jun25840964
Effects of dietary supplementation of fermented Ginkgo biloba L. residues ongrowth performance, nutrient digestibility, serum biochemical parameters andimmune function in weaned piglets.Anim Sci J2015 Aug25827443
Antibiotic resistance and resistance genes in Escherichia coli from poultryfarms, southwest Nigeria.J Infect Dev Ctries2014 Sep 1225212074
Early modulation of the cecal microbial activity in the young rabbit with rapidlyfermentable fiber: impact on health and growth.J Anim Sci2014 Dec25403198
Antimicrobial resistance of Campylobacter jejuni and Campylobacter coli frompoultry in Italy.Microb Drug Resist2014 Apr24320689
Determination of aminoglycoside residues in kidney and honey samples byhydrophilic interaction chromatography-tandem mass spectrometry.J Sep Sci2012 Oct23065931
Simultaneous determination of 15 aminoglycoside(s) residues in animal derivedfoods by automated solid-phase extraction and liquid chromatography-tandem massspectrometry.Food Chem2012 Nov 1522868145
Use of dietary mannanoligosaccharides during rabbit fattening period: effects on growth performance, feed nutrient digestibility, carcass traits, and meatquality.J Anim Sci2012 Nov22696621
[Determination of ten aminoglycoside residues in milk and dairy products usinghigh performance liquid chromatography-tandem mass spectrometry].Se Pu2012 Nov23451516
Occurrence of antimicrobial residues in Brazilian food animals in 2008 and 2009.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201222129165
Antimicrobial susceptibility of Pasteurella multocida isolated from swine and poultry.Acta Vet Hung2009 Sep19635708
Salmonella Indiana as a cause of abortion in ewes: Genetic diversity andresistance patterns.Vet Microbiol2009 Mar 218823722
Effects of in-feed egg yolk antibodies on Salmonella shedding, bacterialantibiotic resistance, and health of pigs.J Food Prot2009 Feb19350971
Multi-residue quantitation of aminoglycoside antibiotics in kidney and meat byliquid chromatography with tandem mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2008Dec19680860
Antimicrobial resistance of Salmonella enterica isolates from apparently healthy and clinically ill finishing pigs in Spain.Zoonoses Public Health2008 May18387141