KANAMYCIN

KANAMYCIN Basic information
Description Sources
Product Name:KANAMYCIN
Synonyms:o-6-deoxy-alpha-d-glucopyranosyl-(1.fwdarw.)]-2-deoxy-;y-alpha-d-glucopyranosyl-(1-4))-2-deoxy-;Kannamycin Monosulfate;KANAMYCIN BASE ENTERPRISE STANDARD;KanamycinMonosulfateA;1-O-[(1R)-2α-Hydroxy-3β-(3-amino-3-deoxy-α-D-glucopyranosyloxy)-4α,6α-diaminocyclohexane-1β-yl]-6-amino-6-deoxy-α-D-glucopyranose;4-O-(6-Amino-6-deoxy-α-D-glucopyranosyl)-6-O-(3-amino-3-deoxy-α-D-glucopyranosyl)-2-deoxy-D-streptamine;(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-methylol-tetrahydropyran-2-yl]oxy-2-hydroxy-cyclohexoxy]tetrahydropyran-3,4,5-triol
CAS:59-01-8
MF:C18H36N4O11
MW:484.5
EINECS:200-411-7
Product Categories:
Mol File:59-01-8.mol
KANAMYCIN Structure
KANAMYCIN Chemical Properties
Melting point >175°C (dec.)
alpha D24 +146° (0.1N H2SO4)
Boiling point 581.13°C (rough estimate)
density 1.4042 (rough estimate)
refractive index 1.6700 (estimate)
storage temp. 2-8°C
solubility Methanol (Slightly, Sonicated), Water (Slightly)
pkapKa 6.40/7.55/8.40/9.40(H2O) (Uncertain)
form liquid
color White to Off-White
EPA Substance Registry SystemD-Streptamine, O-3-amino-3-deoxy-.alpha.-D-glucopyranosyl-(1.fwdarw.6)-O-[6-amino-6-deoxy-.alpha.-D-glucopyranosyl-(1.fwdarw.4)]-2-deoxy- (59-01-8)
Safety Information
WGK Germany 2
Hazardous Substances Data59-01-8(Hazardous Substances Data)
ToxicityLD50 i.v. in mice: 583 mg/kg (Wakazawa)
MSDS Information
ProviderLanguage
SigmaAldrich English
KANAMYCIN Usage And Synthesis
DescriptionKanamycin is a well-known bactericidal antibiotic. It belongs to the aminoglycoside antibiotic group. It can be used for the treatment of various pathogens including E. coli, Proteus species (both indole-positive and indole-negative), Enterobacter aerogenes, Klebsiella pneumoniae, Serratia marcescens and Acinetobacter species1-4. Kanamycin is isolated from the bacterium Streptomyces kanamyceticus and its most commonly used form is kanamycin sulfate5. Aminoglycoside-type drug take actions through “irreversibly” binding to the 30S subunit of the ribosome, further blocking the protein synthesis. Kanamycin kills bacteria cells binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes5.
Sources
  1. Pindell, M. H. "The pharmacology of kanamycin--a review and new developments." Annals of the New York Academy of Sciences 132.2(1966): 805–810.
  2. https://www.annualreviews.org/doi/pdf/10.1146/annurev.bi.42.070173.002351
  3. Spelman, D. W., M. Mcdonald, and W. J. Spicer. "Aminoglycoside antibiotic agents: a review." Medical Journal of Australia 151.6(1989): 346.
  4. https://en.wikipedia.org/wiki/Kanamycin_A
  5. https://www.drugbank.ca/drugs/DB01172
UsesKanamycin A is an antibiotic complex produced by Streptomyces kanamyceticus Okami & Umezawa from Japanese soil. Comprised of three components, kanamycin A, the major component, and kanamycins B and C, two minor congeners. Antibacterial.
UsesAntibacterial Kantrex (Apothecon).
IndicationsKanamycin, O-3-amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[6-deoxy- 6-amino-α-D-glucopyranosyl-(1→4)]–2-deoxy-D-streptamine (32.4.6), is isolated from a culture fluid of the actinomycete Streptomyces kanamyceticus, which produces three antibiotics—kanamycins A, B, and C.
Kanamycin A is similar to streptomycin and neomycines, and it possesses a broad spectrum of antimicrobial action. It is active with respect to most Gram-positive and Gramnegative microorganisms (staphylococci, colon bacillus, klebisella, Fridlender’s bacillus, proteus, shigella, salmonella).
It is used to treat sepsis, meningitis, osteomyelitis, peritonitis, pneumonia, pyelonephritis, pyelocystitis, infected wounds, and post-operational, purulent complications that are caused by microorganisms sensitive to this drug. Kanamycin is used to treat tuberculosis of the lungs and other organs upon resistance to other antituberculosis drugs. Synonyms of this drug are karmycin, kamaxin, resistomycin, and many others.

DefinitionChEBI: Kanamycin A is a member of kanamycins. It has a role as a bacterial metabolite. It is a conjugate base of a kanamycin A(4+).
Brand nameKlebcil (King).
Antimicrobial activityIt is active against staphylococci, including methicillin-resistant strains. Other aerobic and anaerobic Gram-positive cocci and most Gram-positive rods are resistant, but M. tuberculosis is susceptible. It is widely active against most aerobic Gram-negative rods, except Burkholderia cepacia and Sten. maltophilia. Treponema pallidum, Leptospira and Mycoplasma spp. are all resistant.
Acquired resistanceResistance is usually plasmid borne and due to enzymatic inactivation of the drug by enzymes that also inactivate gentamicin or tobramycin . Resistance due to reduced permeability is also encountered.
PharmacokineticsCmax 500 mg intramuscular: c.15–20 mg/L after 1 h
Plasma half-life: 2.5 h
Volume of distribution: 0.3 L/kg
Plasma protein binding: Low
Absorption and distribution
Very little is absorbed from the intestinal tract. The peak plasma concentration in the neonate is dose related: concentrations of 8–30 mg/L (mean 18 mg/L) have been found 1 h after a 10 mg/kg dose. The drug is confined to the extracellular fluid. The concentration in serous fluids is said to equal that in the plasma, but it does not enter the CSF in therapeutically useful concentrations even in the presence of meningeal inflammation.
Excretion
It is excreted almost entirely by the kidneys, almost exclusively in the glomerular filtrate. Up to 80% of the dose appears unchanged in the urine over the first 24 h, producing concentrations around 100–500 mg/L. It is retained in proportion to reduction in renal function. Less than 1% of the dose appears in the bile. In patients receiving 500 mg intramuscularly preoperatively, concentrations of 2–23 mg/L have been found in bile and 8–14 mg/kg in gallbladder wall.






Clinical UseFormerly used for severe infection with susceptible organisms, it has largely been superseded by other aminoglycosides.
Side effectsIntramuscular injections are moderately painful, and minor side effects similar to those encountered with streptomycin have been described. Eosinophilia in the absence of other manifestations of allergy occurs in up to 10% of patients. Other manifestations of hypersensitivity are rare.
As with other aminoglycosides, the most important toxic effects are on the eighth nerve and much less frequently on the kidney. Renal damage is seen principally in patients with pre-existing renal disease or treated concurrently or sequentially with other potentially nephrotoxic agents. The drug accumulates in the renal cortex, producing cloudy swelling, which may progress to acute necrosis of proximal tubular cells with oliguric renal failure. Less dramatic deterioration of renal function, particularly exaggeration of the potential nephrotoxicity of other drugs or of existing renal disease, is of principal importance because it increases the likelihood of ototoxicity.
Vestibular damage is uncommon but may be severe and prolonged. Hearing damage is usually bilateral, and typically affects frequencies above the conversational range. Acute toxicity is most likely in patients in whom the plasma concentration exceeds 30 mg/L, but chronic toxicity may be seen in patients treated with the drug over long periods. Auditory toxicity may be potentiated by concurrent treatment with potent diuretics like ethacrynic acid. If tinnitus – which usually heralds the onset of auditory injury – develops, the drug should be withdrawn.
Neuromuscular blockade is seen particularly in patients receiving other muscle relaxants or suffering from myasthenia gravis and may be reversed by neostigmine.
KANAMYCIN ACID SULFATE,KANAMYCIN ACID SULPHATE,Kanamycin A disulfate salt,KANAMYCIN A ACID SULFATE E. coli growth agar with kanamycin, IPTG and X-gal, ready to use L-(-)-N-BENZOXYLCARBONYL-ALPHA-HYDROXY-GAMMA-AMINO BUTYRIC ACID AMIKACIN Antibiotic Test disks, Kanamycin Susceptibility Test disks N'-[(S)-4-Amino-2-hydroxybutyl]kanamycin A KANAMYCIN Kanamycin sulfate ANTI-KANAMYCIN KANAMYCIN BASE,KANAMYCIN A,KANAMYCIN KANAMYCIN POSITIVE CONTROL RNA AMIKACIN SULFATE SALT Amikacin sulfate salt KANAMYCIN B SULFATE,KANAMYCIN B SULFATE SALT KANAMYCIN B 1-N-[L(-)-4-AMINO-2-HYDROXY-BUTYRYL]KANAMYCIN A KANAMYCIN MONOSULPHATE ANTI-HUMAN KANAMYCIN-BSA,ANTI-KANAMYCIN-BSA KANAMYCIN SULFATE

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