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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| Clinical data | |
| Trade names | Amikin |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a682661 |
| Pregnancy cat. | D(AU) C(US) |
| Legal status | POM (UK) ℞-only (US) |
| Routes | Intramuscular, intravenous |
| Pharmacokinetic data | |
| Protein binding | 0-11% |
| Half-life | 2-3 hours |
| Excretion | Renal |
| Identifiers | |
| CAS number | 37517-28-5  |
| ATC code | D06AX12 J01GB06, S01AA21 |
| PubChem | CID 37768 |
| DrugBank | APRD00550 |
| ChemSpider | 34635 |
| UNII | 84319SGC3C |
| KEGG | D02543 |
| ChEBI | CHEBI:2637 |
| ChEMBL | CHEMBL177 |
| Chemical data | |
| Formula | C22H43N5O13 |
| Mol. mass | 585.603 g/mol |
| SMILES | eMolecules & PubChem |
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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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[edit] 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 as amikacin is not absorbed orally. In people with kidney failure, dosage must be adjusted according to the creatinine clearance, usually by reducing the dosing frequency.
[edit] 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. Serratia marcescens and Providencia stuartii are also included in the spectrum. Amikacin can also be used to treat non tubercular mycobacterial infections and tuberculosis (if caused by sensitive strains) when first line drugs fail to control the infection.
Amikacin may be combined with a beta-lactam antibiotic for empiric therapy for people with neutropenia and fever.
[edit] 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.
[edit] 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. Moreover, doses are adjusted specifically based upon serum Creatinine clearance in clinical settings.[citation needed]
[edit] References
- Edson RS, Terrell CL. The aminoglycosides. Mayo Clin Proc. 1999 May;74(5):519-28. Review. PMID 10319086
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