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Product Description
Mechanism of action
Amikacin is a semi-synthetic aminoglycoside antibiotic derived from kanamycin A. It binds irreversibly to the 30S subunit of bacterial ribosomes, causing misreading of mRNA and premature termination of protein synthesis. This leads to the production of non-functional or toxic peptides and ultimately bacterial cell death. Amikacin has activity against a broad spectrum of aerobic Gram-negative bacilli, including many strains resistant to other aminoglycosides.
Benefits and advantages
Because of its stability against many aminoglycoside-modifying enzymes, amikacin is often reserved for severe or complicated infections caused by multidrug-resistant Gram-negative organisms, including Pseudomonas and Acinetobacter species. It is used in hospital settings for systemic infections such as sepsis, respiratory infections and complicated urinary tract infections, usually in combination with other agents as part of empiric or targeted therapy.
Side effects and risks
Major toxicities of aminoglycosides are nephrotoxicity and ototoxicity (both cochlear and vestibular), which are related to cumulative dose and high serum concentrations. Neuromuscular blockade and allergic reactions are less common but clinically relevant. Serum-level monitoring and dose adjustment in renal impairment are critical to minimise risk. The raw material must be handled under suitable containment to avoid inhalation of antibiotic powder and to limit environmental release.
Professional use only. Supplied exclusively to licensed pharmaceutical manufacturers and healthcare institutions.
Datasheet
| Molecular Formula | C22H43N5O13 |
|---|---|
| Molecular Weight | 585.6 g/mol |
| CAS Number | 37517-28-5 |
| Storage Condition | Store at 20 deg to 25 °C (68 deg to 77 °F); excursions permitted between 15 deg to 30 °C (59 deg to 86 °F) |
| Solubility | Solubility depends on solvent and conditions (e.g., pH). Please contact us for solvent-specific guidance. |
| Purity | Purity information is available upon request (COA). |
| Synonym | amikacin; 37517-28-5; Lukadin; amikacine; Amikacina |
| IUPAC/Chemical Name | (2S)-4-amino-N-[(1R,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,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide |
| InChl Key | LKCWBDHBTVXHDL-RMDFUYIESA-N |
| InChl Code | InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1 |
| References |
3D Conformer.
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