Gentamicin

Basic Info

Common NameGentamicin(F05894)
2D Structure
FRCD IDF05894
CAS Number
PubChem CID3467
FormulaC21H43N5O7
IUPAC Name

2-[4,6-diamino-3-[3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol

InChI Key

CEAZRRDELHUEMR-UHFFFAOYSA-N

InChI

InChI=1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3

Canonical SMILES

CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC

Isomeric SMILES

CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC

Synonyms
        
            Gentavet
        
            Refobacin
        
            gentamicin
        
            Gentacycol
        
            Garamycin
        
            Gentamicins
        
            Gentamicinum
        
            Gentamycinum
        
            Cidomycin
        
            Garasol
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 heteromonocyclic compounds
SubstituentsAmino cyclitol glycoside - 2-deoxystreptamine aminoglycoside - Glycosyl compound - O-glycosyl compound - Aminocyclitol or derivatives - Cyclohexanol - Cyclohexylamine - Cyclitol or derivatives - Monosaccharide - Oxane - Tertiary alcohol - Cyclic alcohol - Secondary alcohol - 1,2-aminoalcohol - Secondary amine - Acetal - Organoheterocyclic compound - Secondary aliphatic amine - Oxacycle - Alcohol - Hydrocarbon derivative - Primary aliphatic amine - Organopnictogen compound - Organic nitrogen compound - Amine - Primary amine - Organonitrogen compound - Aliphatic heteromonocyclic 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 Weight477.603
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count12
Rotatable Bond Count7
Complexity636
Monoisotopic Mass477.316
Exact Mass477.316
XLogP-4.1
Formal Charge0
Heavy Atom Count33
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count13
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9826
Human Intestinal AbsorptionHIA-0.9440
Caco-2 PermeabilityCaco2-0.6987
P-glycoprotein SubstrateSubstrate0.6882
P-glycoprotein InhibitorNon-inhibitor0.6808
Non-inhibitor0.9586
Renal Organic Cation TransporterNon-inhibitor0.8738
Distribution
Subcellular localizationLysosome0.6360
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8001
CYP450 2D6 SubstrateNon-substrate0.8314
CYP450 3A4 SubstrateSubstrate0.5917
CYP450 1A2 InhibitorNon-inhibitor0.9034
CYP450 2C9 InhibitorNon-inhibitor0.8910
CYP450 2D6 InhibitorNon-inhibitor0.9331
CYP450 2C19 InhibitorNon-inhibitor0.9043
CYP450 3A4 InhibitorNon-inhibitor0.9517
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9294
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9954
Non-inhibitor0.8784
AMES ToxicityNon AMES toxic0.7338
CarcinogensNon-carcinogens0.9696
Fish ToxicityLow FHMT0.9232
Tetrahymena Pyriformis ToxicityHigh TPT0.9227
Honey Bee ToxicityLow HBT0.5998
BiodegradationNot ready biodegradable0.9588
Acute Oral ToxicityIII0.5659
Carcinogenicity (Three-class)Non-required0.5967
Model Value Unit
Absorption
Aqueous solubility-2.1378LogS
Caco-2 Permeability0.0878LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0383LD50, mol/kg
Fish Toxicity1.8859pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3497pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Poultry Animals,Edible OffalJapan0.1ppm
Chicken,Edible OffalJapan0.1ppm
Other Poultry Animals,KidneyJapan0.1ppm
Chicken,KidneyJapan0.1ppm
Other Poultry Animals,LiverJapan0.1ppm
Chicken,LiverJapan0.1ppm
Other Poultry Animals,FatJapan0.1ppm
Chicken,FatJapan0.1ppm
Other Poultry Animals,MuscleJapan0.1ppm
Chicken,MuscleJapan0.1ppm
Pig,Edible OffalJapan2ppm
Cattle,Edible OffalJapan2ppm
MilkJapan0.2ppm
Pig,KidneyJapan5. oppm
Cattle,KidneyJapan5. oppm
Pig,LiverJapan2. oppm
Cattle,LiverJapan2. oppm
Pig,FatJapan0.1ppm
Cattle,FatJapan0.1ppm
Pig,MuscleJapan0.1ppm

References

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Determination of antibiotic resistance of lactic acid bacteria isolated fromtraditional Turkish fermented dairy products.Iran J Vet Res2018 Winter29805464
Associations between a decreased veterinary antimicrobial use and resistance incommensal Escherichia coli from Belgian livestock species (2011-2015).Prev Vet Med2018 Sep 130086849
Prevalence, bioserotyping and antibiotic resistance of pathogenic Yersiniaenterocolitica detected in pigs at slaughter in Sardinia.Int J Food Microbiol2018 Oct 2029929063
ESBL- and AmpC-producing Escherichia coli from legally and illegally importedmeat: Characterization of isolates brought into the EU from third countries.Int J Food Microbiol2018 Oct 2030099995
Prevalence, Enterotoxin Genes, and Antibiotic Resistance of Bacillus cereus Isolated from Raw Vegetables in Korea.J Food Prot2018 Oct30169119
Emergence of mcr-1 plasmid-mediated colistin-resistant Escherichia coli isolates from seawater.Sci Total Environ2018 Nov 1529894885
Safety Evaluations of <i>Bifidobacterium bifidum</i> BGN4 and <i>Bifidobacterium longum</i> BORI.Int J Mol Sci2018 May 929747442
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
Enumerating Antibiotic Susceptibility Patterns of Pseudomonas aeruginosa Isolatedfrom Different Sources in Dhaka City.Open Microbiol J2018 May 3129997702
Antibiotic resistance phenotypes and virulence-associated genes in Escherichiacoli isolated from animals and animal food products in Tunisia.FEMS Microbiol Lett2018 May 129635468
UPLC-MS/MS analysis of antibiotics in pharmaceutical effluent in Tunisia:ecotoxicological impact and multi-resistant bacteria dissemination.Arch Microbiol2018 May29230492
First Detection of FOX-1 AmpC β-lactamase Gene Expression Among Escherichia coli Isolated from Abattoir Samples in Abakaliki, Nigeria.Oman Med J2018 May29896333
Antibiotic Residues in Milk from Three Popular Kenyan Milk Vending Machines.Am J Trop Med Hyg2018 May29557339
Prevalence, Virulence Genes, Antimicrobial Susceptibility, and Genetic Diversity of Bacillus cereus Isolated From Pasteurized Milk in China.Front Microbiol2018 Mar 2629632521
Most commensally bacterial strains in human milk of healthy mothers displaymultiple antibiotic resistance.Microbiologyopen2018 Mar 25:e0061829577668
Emergence of plasmid-mediated colistin-resistance in CMY-2-producing Escherichia coli of lineage ST2197 in a Tunisian poultry farm.Int J Food Microbiol2018 Mar 2329421359
Antimicrobial susceptibility of enterococci recovered from healthy cattle, pigsand chickens in nine EU countries (EASSA Study) to critically importantantibiotics.Vet Microbiol2018 Mar29519512
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
In vitro activity of Nigella sativa against antibiotic resistant Salmonellaenterica.Environ Toxicol Pharmacol2018 Mar29289818
Regulation of CD4+CD8-CD25+ and CD4+CD8+CD25+ T cells by gut microbiota inchicken.Sci Rep2018 Jun 529872084