Amikacin

Amikacin

File:Amikacin.svg
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
Clinical data
Pregnancy category	AU: D US: C (Risk not ruled out)
Routes of administration	Intramuscular, intravenous
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Protein binding	0-11%
Biological half-life	2-3 hours
Excretion	Renal
Identifiers
CAS Number	37517-28-5
ATC code	D06AX12 (WHO) J01GB06, S01AA21
PubChem	CID 37768
DrugBank	APRD00550
ChemSpider	34635
Chemical data
Formula	C22H43N5O13
Molar mass	585.603 g/mol[[]]

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. 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 extremely powerful antibiotic, its use is tightly regulated.

Side 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

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