Kanamycin

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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

Identifiers
CAS number 8063-07-8
ATC code A07AA08 J01GB04 S01AA24
PubChem 6032
DrugBank APRD00026
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

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Routes Oral, intravenous, intramuscular

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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 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.

Because of over-usage of antibiotics many bacteria have developed a resistance against kanamycin, and, consequently, it is not used much anymore.

Side effects

Common side effects include changes in hearing (either hearing loss or ringing in the ears), toxicity to kidneys, and allergic reactions to the drug.

Use in Research

Genes encoding kanamycin resistance are commonly used as selectable markers in molecular biology.

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Acknowledgement and Attribution Regarding Sources of Content

Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .

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