Kanamycin
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| 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  |
| ATC code | A07AA08 J01GB04 S01AA24 |
| PubChem | CID 6032 |
| DrugBank | APRD00026 |
| ChemSpider | 5810 |
| UNII | RUC37XUP2P |
| ChEBI | CHEBI:17630 |
| ChEMBL | CHEMBL1384 |
| Chemical data | |
| Formula | C18H36N4O11 |
| Mol. mass | 484.499 |
| SMILES | eMolecules & PubChem |
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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 kanamyceticus1 and used in form of the sulfate.
Contents
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Mechanism
Kanamycin interacts with the 30S subunit of prokaryotic ribosomes. It induces substantial amounts of mistranslation and indirectly inhibits translocation during protein synthesis.23
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, Atwbc195 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
- ^ Garrod, L.P., et al.: "Antibiotic and Chemotherapy", page 131. Churchill Livingstone, 1981
- ^ Pestka, S.: "The Use of Inhibitors in Studies on Protein Synthesis", Methods in Enzymology 30, pp.261-282, 1975
- ^ Misumi, M. & Tanaka, N.: "Mechanism of Inhibition of Translocation by Kanamycin and Viomycin: A Comparative Study with Fusidic Acid, Biochem.Biophys.Res.Commun. 92, pp.647-654, 1980
- ^ Consumer Drug Information: Kanamycin, 2 April 2008, http://www.drugs.com/cdi/kanamycin.html, retrieved 2008-05-04
- ^ Horizontal Gene Transfer: Plant vs. Bacterial Genes for Antibiotic Resistance Scenario's—What's the Difference?
External links
Technical Information from kanamycin-evopure.com [1]
- Purity Survey: [2]
- Toxicity Data: [3]
- Working Concentrations: [4]
- Kanamycin Impurities: [5]
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