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Amikacin
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| 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 |
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| Identifiers | |
| CAS number | |
| ATC code | D06 J01GB06, S01AA21 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C22H43N5O13 |
| Mol. mass | 585.603 g/mol |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Protein binding | 0-11% |
| Metabolism | ? |
| Half life | 2-3 hours |
| Excretion | Renal |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status | |
| 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.
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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). Due to the fact that this is a very powerful anti-biotic. Its use is tightly regulated to prevent bacterial resistance developing.
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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Wikipedia content modification information:
- This page was last modified on 20 June 2008, at 06:42.
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