Kanamycin
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Kanamycin
Systematic (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
Identifiers
CAS number	8063-07-8
ATC code	A07AA08 J01GB04 S01AA24
PubChem	6032
DrugBank	APRD00026
Chemical data
Formula	C18H36N4O11
Mol. mass	484.499
Pharmacokinetic data
Bioavailability	very low after oral delivery
Metabolism	?
Half life	2 hours 30 minutes
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	?
Routes	Oral, intravenous, intramuscular

Kanamycin sulfate is an aminoglycoside antibiotic, available in both oral and intravenous forms, and used to treat a wide variety of infections. Kanamycin is isolated from Streptomyces kanamyceticus^[1].

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.^{citation needed}

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

Side 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.^[2]

Use in research

Genes encoding kanamycin resistance are commonly used as selectable markers in molecular biology.^{citation needed} At least one such gene, Atwbc19^[3] 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