Kanamycin

Kanamycin

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Clinical data
Pregnancy category	?
Routes of administration	Oral, intravenous, intramuscular
ATC code	A07AA08 (WHO) J01GB04 (WHO) S01AA24 (WHO)
Legal status
Legal status	?
Pharmacokinetic data
Bioavailability	very low after oral delivery
Metabolism	?
Elimination half-life	2 hours 30 minutes
Excretion	?
Identifiers
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
CAS Number	8063-07-8
PubChem CID	6032
DrugBank	APRD00026
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C18H36N4O11
Molar mass	484.499

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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.

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.

Because of over-usage of antibiotics many bacteria have developed a resistance against kanamycin, and, consequently, it is not used much anymore.

Side effects

Common side effects include changes in hearing (either hearing loss or ringing in the ears), toxicity to kidneys, and allergic reactions to the drug.

Use in Research

Genes encoding kanamycin resistance are commonly used as selectable markers in molecular biology.

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