Amikacin

drugbox
IUPAC_name = (2"S")-4-amino-N- [(2"S",3"S",4"R",5"S")-5-amino-2-
[(2"S",3"R",4"S",5"S",6"R")-4-amino-3,5-dihydroxy-
6-(hydroxymethyl)oxan-2-yl] oxy-4- [(2"R",3"R",
4"S",5"R",6"R")-6-(aminomethyl)-3,4,5-trihydroxy-
oxan-2-yl] oxy-3-hydroxy-cyclohexyl] -2-hydroxy-
butanamide

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CAS_number = 37517-28-5
ATC_prefix = D06
ATC_suffix = AX12
ATC_supplemental = ATC|J01|GB06, ATC|S01|AA21
PubChem = 441188
DrugBank = APRD00550
C = 22 | H = 43 | N = 5 | O = 13
molecular_weight = 585.603 g/mol
bioavailability =
protein_bound = 0-11%
metabolism =
elimination_half-life = 2-3 hours
excretion = Renal
pregnancy_AU = D
pregnancy_US = C
legal_UK = POM
legal_US = Rx-only
routes_of_administration = Intramuscular, intravenous

Amikacin is an aminoglycoside antibiotic used to treat different types of bacterial infections. Amikacin works by binding to the bacterial 30S ribosomal subunit, causing misreading of mRNA and leaving the bacterium unable to synthesize proteins vital to its growth.

Administration

Amikacin may be administered once or twice a day but must be given by the intravenous or intramuscular route, which tends to be painful. There is no oral form available. Dosage must be adjusted in people with kidney failure.

Uses

Amikacin is most often used for treating severe, hospital-acquired infections with multidrug resistant Gram negative bacteria such as "Pseudomonas aeruginosa", "Acinetobacter", and "Enterobacter".

Amikacin may be combined with a beta-lactam antibiotic for empiric therapy for people with neutropenia and fever.

Resistance

Amikacin has high resistance against bacterial inactivation. It resists attacks by most bacterial inactivating enzymes, this is accomplished by the L-hydroxyaminobuteroyl amide (L-HABA) moiety attached to N-3 which inhibits acetylation, phosphorylation and adenylation in the distant amino sugar ring (C-2,C-3,C-4). To prevent the development of bacterial resistance to this very powerful antibiotic, its use is tightly regulated.

ide effects

Side effects of amikacin are similar to other aminoglycosides. Kidney damage and hearing loss are the most important effects. Because of this potential, blood levels of the drug and markers of kidney function (creatinine) may be monitored.

References

* Edson RS, Terrell CL. "The aminoglycosides." Mayo Clin Proc. 1999 May;74(5):519-28. Review. PMID 10319086