Amikacin

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Image:Amikacin.svg
Amikacin
Systematic (IUPAC) name
(2S)-4-amino-N-[(2S,3S,4R,5S)-5-amino-2- [(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy- 6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3R, 4S,5R,6R)-6-(aminomethyl)-3,4,5-trihydroxy- oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy- butanamide
Identifiers
CAS number	37517-28-5
ATC code	D06 AX12 J01 GB06, S01 AA21
PubChem	441188
DrugBank	APRD00550
Chemical data
Formula	C₂₂H₄₃N₅O₁₃
Mol. weight	585.603 g/mol
Pharmacokinetic data
Bioavailability	?
Protein binding	0-11%
Metabolism	?
Half life	2-3 hours
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	D(AU) C(US)
Legal status	POM(UK) ℞-only(US)
Routes	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.

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

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.

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.