Kanamycin

Kanamycin

File:Kanamycin A.svg
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
Clinical data
Pregnancy category	D
Routes of administration	Oral, intravenous, intramuscular
Legal status
Legal status	?
Pharmacokinetic data
Bioavailability	very low after oral delivery
Metabolism	Unknown
Biological half-life	2 hours 30 minutes
Excretion	Urine (as unchanged drug)
Identifiers
CAS Number	59-01-8
ATC code	A07AA08 (WHO) J01GB04 S01AA24
PubChem	CID 6032
DrugBank	APRD00026
Chemical data
Formula	C18H36N4O11
Molar mass	484.499[[]]

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 interacts with the 30S subunit of prokaryotic ribosomes. It induces substantial amounts of mistranslation and indirectly inhibits translocation during protein synthesis.

Side effects

Serious side effects include tinnitus or loss of hearing, toxicity to kidneys, and allergic reactions to the drug.

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 (primarily Neomycin phosphotransferase II [NPT II/Neo]). Bacteria that have been transformed with a plasmid containing the kanamycin resistance gene are plated on kanamycin (50-100ug/ml) containing agar plates or are grown in media containing kanamycin (50-100ug/ml). 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).

Mammalian cells and other eukaryotes are screened using G418, a similar aminoglycoside antibiotic, which KanMX confers resistance against.

At least one such gene, Atwbc19 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

af:Kannamisien zh:卡纳霉素