Gentamicin

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Gentamicin chemical structure
Gentamicin
Systematic (IUPAC) name
2-[4,6-diamino-3- [3-amino-6-(1-methylaminoethyl) tetrahydropyran-2-yl] oxy-2-hydroxy- cyclohexoxy]-5-methyl- 4-methylamino-tetrahydropyran-3,5-diol
Identifiers
CAS number 1403-66-3
ATC code D06AX07 J01GB03, S01AA11, S02AA14, S03AA06
PubChem 3467
DrugBank APRD00214
Chemical data
Formula C21H43N5O7
Mol. weight 477.596 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

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Legal status
Routes  ?

Gentamicin (also gentamycin) is an aminoglycoside antibiotic, and can treat many different types of bacterial infections, particularly Gram-negative infection. However, gentamicin is not used for Neisseria gonorrheae, Neisseria meningitidis or Legionella pneumophila infections.

Gentamicin works by binding to a site on the bacterial ribosome, causing the genetic code to be misread.

Like all aminoglycosides, when gentamicin is given orally, it is not effective. This is because it is absorbed from the small intestine, and then travels through the portal vein to the liver, where it is inactivated. Therefore, it can only be given intravenously, intramuscularly or topically.

E. Coli has shown some resistance to gentamicin, despite being Gram-negative.

Gentamicin is one of the few heat-stable antibiotics that remain active even after autoclaving, which makes it particularly useful in the preparation of certain microbiological growth media.

[edit] Side effects

Gentamicin can cause deafness or a loss of equilibrioception in genetically susceptible individuals. These individuals have a normally harmless mutation in their DNA, that allows the gentamicin to affect their cells. The cells of the ear are particularly sensitive to this. It is sometimes used intentionally for this purpose in severe Ménière’s disease, to disable the vestibular apparatus.

Gentamicin can also be highly nephrotoxic, particularly if multiple doses accumulate over a course of treatment. For this reason gentamicin is usually dosed by body weight. Various formulae exist for calculating gentamicin dosage. Also serum levels of gentamicin are monitored during treatment.


Aminoglycosides (J01G) edit

Amikacin, Gentamicin, Kanamycin, Neomycin, Netilmicin, Streptomycin, Tobramycin, Paromomycin, Hygromycin, spectinomycin
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