Drug/Small Molecule:
kanamycin

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The annotations do not account for individual variations among patients, and cannot be considered inclusive of all proper methods of care or exclusive of other treatments. It remains the responsibility of the health-care provider to determine the best course of treatment for a patient. Adherence to any guideline is voluntary, with the ultimate determination regarding its application to be made solely by the clinician and the patient. PharmGKB assumes no responsibility for any injury or damage to persons or property arising out of or related to any use of the PharmGKB clinical annotations, or for any errors or omissions.

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This is a non-comprehensive list of genetic tests with pharmacogenetics relevance, typically submitted by the manufacturer and manually curated by PharmGKB. The information listed is provided for educational purposes only and does not constitute an endorsement of any listed test or manufacturer.

A more complete listing of genetic tests is found at the Genetic Testing Registry (GTR).

PGx Test Variants Assayed Gene?
2D structure from PubChem
provided by PubChem

Overview

Generic Names
  • Aminodeoxykanamycin
  • KAN
  • Kanamycin Base
  • Kanamycin Sulfate
  • Nebramycin Factor 5
Trade Names
  • Bekanamycin
  • Kanamycin A
  • Kanamycin B
  • Kenamycin A
  • Klebcil
Brand Mixture Names

PharmGKB Accession Id:
PA450137

Description

Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components.

Source: Drug Bank

Indication

For treatment of infections where one or more of the following are the known or suspected pathogens: E. coli, Proteus species (both indole-positive and indole-negative), E. aerogenes, K. pneumoniae, S. marcescens, and Acinetobacter species.

Source: Drug Bank

Other Vocabularies

Information pulled from DrugBank has not been reviewed by PharmGKB.

Pharmacology, Interactions, and Contraindications

Mechanism of Action

Aminoglycosides like kanamycin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically Kanamycin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes.

Source: Drug Bank

Pharmacology

Kanamycin is an aminoglycoside antibiotic. Aminoglycosides work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. In addition, some mycobacteria, including the bacteria that cause tuberculosis, are susceptible to aminoglycosides. Infections caused by Gram-positive bacteria can also be treated with aminoglycosides, but other types of antibiotics are more potent and less damaging to the host. In the past the aminoglycosides have been used in conjunction with penicillin-related antibiotics in streptococcal infections for their synergistic effects, particularly in endocarditis. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses.

Source: Drug Bank

Absorption, Distribution, Metabolism, Elimination & Toxicity

Absorption

Kanamycin is rapidly absorbed after intramuscular injection and peak serum levels are generally reached within approximately one hour. Poor oral and topical absorption except with severe skin damage.

Source: Drug Bank

Half-Life

2.5 hours

Source: Drug Bank

Toxicity

Mild and reversible nephrotoxicity may be observed in 5 - 25% of patients. Amikacin accumulates in proximal renal tubular cells. Tubular cell regeneration occurs despite continued drug exposure. Toxicity usually occurs several days following initiation of therapy. May cause irreversible ototoxicity. Otoxocity appears to be correlated to cumulative lifetime exposure. Drug accumulation in the endolymph and perilymph of the inner ear causes irreversible damage to hair cells of the cochlea or summit of ampullar cristae in the vestibular complex. High frequency hearing is lost first with progression leading to loss of low frequency hearing. Further toxicity may lead to retrograde degeneration of the 8th cranial (vestibulocochlear) nerve. Vestibular toxicity may cause vertigo, nausea, vomiting, dizziness and loss of balance.
Oral LD50 is 17500 mg/kg in mice, over 4 g/kg in rats, and over 3 g/kg in rabbits.

Source: Drug Bank

Chemical Properties

Chemical Formula

C18H36N4O11

Source: Drug Bank

Isomeric SMILES

C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)N)O)N

Source: Drug Bank

NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

Source: Drug Bank

Canonical SMILES

NC[C@H]1O[C@H]

Source: Drug Bank

Average Molecular Weight

484.4986

Source: Drug Bank

Monoisotopic Molecular Weight

484.238058014

Source: Drug Bank

Genes that are associated with this drug in PharmGKB's database based on (1) variant annotations, (2) literature review, (3) pathways or (4) information automatically retrieved from DrugBank, depending on the "evidence" and "source" listed below.

No related genes are available.

Drug Interactions

Drug Description
kanamycin Increased ototoxicity (source: Drug Bank)
kanamycin Increased ototoxicity (source: Drug Bank)
kanamycin Increased risk of nephrotoxicity (source: Drug Bank)
kanamycin Increased risk of nephrotoxicity (source: Drug Bank)
kanamycin Increased risk of nephrotoxicity (source: Drug Bank)
kanamycin Increased risk of nephrotoxicity (source: Drug Bank)
kanamycin Increased risk of nephrotoxicity (source: Drug Bank)
kanamycin Increased risk of nephrotoxicity (source: Drug Bank)
kanamycin Increased risk of nephrotoxicity (source: Drug Bank)
kanamycin Increased risk of nephrotoxicity (source: Drug Bank)
kanamycin Increased risk of nephrotoxicity (source: Drug Bank)
kanamycin Increased ototoxicity (source: Drug Bank)
kanamycin Increased ototoxicity (source: Drug Bank)
kanamycin Increased ototoxicity (source: Drug Bank)
kanamycin Increased ototoxicity (source: Drug Bank)
kanamycin Ticarcillin may reduce the serum concentration of Kanamycin. Ticarcillin may inactivate Kanamycin in vitro and the two agents should not be administered simultaneously through the same IV line. (source: Drug Bank)

LinkOuts

Web Resource:
Wikipedia
National Drug Code Directory:
0015-3503-20
DrugBank:
DB01172
ChEBI:
17630
24945
KEGG Compound:
C00304
PubChem Compound:
6032
PubChem Substance:
46508178
ChemSpider:
5810
Therapeutic Targets Database:
DNC000201

Clinical Trials

These are trials that mention kanamycin and are related to either pharmacogenetics or pharmacogenomics.

Common Searches

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Sources for PharmGKB drug information: DrugBank, Open Eye Scientific Software.