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 kanamyceticus[1] and used in form of the sulfate.
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[edit] 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]
[edit] Side effects
Serious side effects include tinnitus or loss of hearing, toxicity to kidneys, and allergic reactions to the drug.[4]
[edit] 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.
[edit] 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?
[edit] External links
Technical Information from kanamycin-evopure.com [1]
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