kanamycin

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
Clinical data
AHFS/Drugs.com	monograph
Pregnancy cat.	D
Legal status	?
Routes	Oral, intravenous, intramuscular
Pharmacokinetic data
Bioavailability	very low after oral delivery
Metabolism	Unknown
Half-life	2 hours 30 minutes
Excretion	Urine (as unchanged drug)
Identifiers
CAS number	59-01-8 Y
ATC code	A07AA08 J01GB04 S01AA24
PubChem	CID 6032
DrugBank	APRD00026
ChemSpider	5810 Y
UNII	RUC37XUP2P Y
ChEBI	CHEBI:17630 Y
ChEMBL	CHEMBL1384 Y
Chemical data
Formula	C18H36N4O11
Mol. mass	484.499
SMILES	eMolecules & PubChem
InChI InChI=1S/C18H36N4O11/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17/h4-18,23-29H,1-3,19-22H2/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-/m1/s1 Y Key:SBUJHOSQTJFQJX-NOAMYHISSA-N Y
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Kanamycin (also known as kanamycin A) is an aminoglycoside antibiotic, available in oral, intravenous, and intramuscular forms, and used to treat a wide variety of infections. Kanamycin is isolated from the bacterium Streptomyces kanamyceticus^[1] and used in form of the sulfate.

Mechanism

Kanamycin interacts with the 30S subunit of prokaryotic ribosomes. It induces substantial amounts of mistranslation and indirectly inhibits translocation during protein synthesis.^[2][3]

Side effects

Serious side effects include tinnitus or loss of hearing, toxicity to kidneys, and allergic reactions to the drug.^[4]

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 (50-100 ug/ml) containing agar plates or are grown in media containing kanamycin (50-100 ug/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 (50 mg/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^[5] 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

External links

Technical Information from kanamycin-evopure.com [1]

• Purity Survey: [2]
• Toxicity Data: [3]
• Working Concentrations: [4]
• Kanamycin Impurities: [5]