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kanamycin

 
(kăn'ə-mī'sĭn) pronunciation
n.
A water-soluble broad-spectrum antibiotic, C18H36O11N4, obtained from the soil bacterium Streptomyces kanamyceticus.

[New Latin kanamyc(ēticus), specific epithet of a species of actinomycete (Japanese kana-, golden (from the color of its colonies) + New Latin mycēticus, fungus , from -mycētēs; see -mycete) + -IN.]


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an aminoglycoside antibiotic complex produced by Streptomyces kanamyceticus. It is made up of three components: kanamycin A (in which R1 = NH2, R2 = OH; see structure), the major component, often designated as kanamycin; and two minor congeners, kanamycin B (R1 and R2 = NH2) and kanamycin C (R1 = OH, R2 = NH2). Kanamycin causes misreading during protein synthesis in bacteria, but its target site on the ribosome is apparently different from that of streptomycin. See also kanosamine.

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An aminoglycoside antibiotic used as the sulfate; active against many gram-negative and acid-fast bacteria. Similar to amikacin.


n

An aminoglycoside antibiotic that acts by inhibiting the synthesis of protein in susceptible organisms. Kanamycin requires close clinical supervision because of its potential toxicity and adverse side effects to the auditory and vestibular branches of the eighth cranial nerve and to the renal tubules.

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 YesY
ATC code A07AA08 J01GB04 S01AA24
PubChem CID 6032
DrugBank APRD00026
ChemSpider 5810 YesY
UNII RUC37XUP2P YesY
ChEBI CHEBI:17630 YesY
ChEMBL CHEMBL1384 YesY
Chemical data
Formula C18H36N4O11 
Mol. mass 484.499
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

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.

Contents

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

  1. ^ Garrod, L.P., et al.: "Antibiotic and Chemotherapy", page 131. Churchill Livingstone, 1981
  2. ^ Pestka, S.: "The Use of Inhibitors in Studies on Protein Synthesis", Methods in Enzymology 30, pp.261-282, 1975
  3. ^ 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
  4. ^ Consumer Drug Information: Kanamycin, 2 April 2008, http://www.drugs.com/cdi/kanamycin.html, retrieved 2008-05-04 
  5. ^ 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]

 
 

 

Copyrights:

American Heritage Dictionary. The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved.  Read more
 Oxford Dictionary of Biochemistry. Oxford University Press. Oxford Dictionary of Biochemistry and Molecular Biology © 1997, 2000, 2006 All rights reserved.  Read more
Saunders Veterinary Dictionary. Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved.  Read more
Mosby's Dental Dictionary. Mosby's Dental Dictionary. Copyright © 2004 by Elsevier, Inc. All rights reserved.  Read more
Wikipedia on Answers.com. This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article Kanamycin Read more

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