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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 |
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| Identifiers | |
| CAS number | |
| ATC code | A07 J01 S01 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C18H36N4O11 |
| Mol. mass | 484.499 |
| Pharmacokinetic data | |
| Bioavailability | very low after oral delivery |
| Metabolism | ? |
| Half life | 2 hours 30 minutes |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status |
? |
| Routes | Oral, intravenous, intramuscular |
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[1].
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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.citation needed
Kanamycin is not given to humans often because of its fairly toxic side-effects.
Side effects
Serious side effects include changes in hearing (either hearing loss or ringing in the ears), toxicity to kidneys, and allergic reactions to the drug.[2]
Use in research
Kanamycin is used in molecular biology as a selective agent most commenly to isolate bacteria (e.g., E. coli) which have taken up genes (e.g., of plasmids) coupled to a gene coding for kanamycin resistance. Bacteria that have been transformed (Transformation (genetics)) with a plasmid containing the kanamycin resistance gene are plated on kanamycin (50-100mg/L) containing agar plates or are grown in media containing kanamycin (50-100mg/L). 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). At least one such gene, Atwbc19[3] 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.
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References
- ^ Garrod, L.P., et al.: "Antibiotic and Chemotherapy", page 131. Churchill Livingstone, 1981
- ^ Consumer Drug Information: Kanamycin, 2 April 2008, <http://www.drugs.com/cdi/kanamycin.html>. Retrieved on 4 May 2008
- ^ Horizontal Gene Transfer: Plant vs. Bacterial Genes for Antibiotic Resistance Scenario's—What's the Difference?
Wikipedia content modification information:
- This page was last modified on 2 September 2008, at 14:57.
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