Kanamycin

Drugbox
IUPAC_name = 2-(aminomethyl)- 6- [4,6-diamino-3- [4-amino-3,5-dihydroxy-6-(hydroxymethyl) tetrahydropyran-2-yl] oxy-2-hydroxy-cyclohexoxy] - tetrahydropyran-3,4,5-triol

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CAS_number=8063-07-8
ATC_prefix=A07
ATC_suffix=AA08
ATC_supplemental=ATC|J01|GB04 ATC|S01|AA24
PubChem=6032
DrugBank=APRD00026
C=18 | H=36 | N=4 | O=11
molecular_weight = 484.499
bioavailability= very low after oral delivery
metabolism = ?
elimination_half-life= 2 hours 30 minutes
excretion = ?
pregnancy_category = ?
legal_status = ?
routes_of_administration= Oral, intravenous, intramuscular

Kanamycin sulfate is an aminoglycoside antibiotic, available in both and intravenous forms, and used to treat a wide variety of infections. Kanamycin is isolated from "Streptomyces kanamyceticus" [Garrod, L.P., et al.: "Antibiotic and Chemotherapy", page 131. Churchill Livingstone, 1981] .

Pharmacology

Kanamycin works by affecting the 30S ribosomal subunit and causing a frameshift mutation or it prevents the translation of RNA. This means that instead of a codon CAT (for example in sequence CATG), a codon ATG is read by aminoacyl tRNA (aa-tRNA). Aminoacyl tRNA is consequently carrying a different amino acid, because the anticodon on the aa-tRNA is different. The protein needed cannot be synthesized: depending on the site and severity of the frame shift, either a completely different protein is synthesized, or a protein similar to the one needed is synthesized, but is folded incorrectly. A bacterium is destroyed because it cannot produce any of its proteins correctly.Fact|date=September 2007

Kanamycin is not given to humans often because of its fairly toxic side-effects.

ide effects

Serious side effects include changes in hearing (either hearing loss or ringing in the ears), toxicity to kidneys, and allergic reactions to the drug. [Citation | title = Consumer Drug Information: Kanamycin | date = 2 April 2008 | url = http://www.drugs.com/cdi/kanamycin.html | accessdate = 2008-05-04]

Use in research

Kanamycin is used in molecular biology as a selective agent most commonly to isolate bacteria (e.g., E. coli) which have taken up genes (e.g., of plasmids) coupled to a gene coding for kanamycin resistance. Bacteria that have been transformed (Transformation (genetics)) with a plasmid containing the kanamycin resistance gene are plated on kanamycin (50-100mg/L) containing agar plates or are grown in media containing kanamycin (50-100mg/L). Only the bacteria that have successfully taken up the kanamycin resistance gene become resistant and will grow under these conditions. As a powder kanamycin is white to off-white and is soluble in water (50mg/ml). At least one such gene, "Atwbc19" [ [http://www.isb.vt.edu/articles/oct0501.htm Horizontal Gene Transfer: Plant vs. Bacterial Genes for Antibiotic Resistance Scenario's—What's the Difference?] ] is native to a plant species, of comparatively large size and its coded protein acts in a manner which decreases the possibility of Horizontal Gene Transfer from the plant to bacteria; it may be incapable of giving resistance to kanamycin to bacteria even if gene transfer occurs.

References