Netilmicin Sulfate

- Overview
  - Netilmicin Sulfate is the sulfate salt form of Netilmicin, a semisynthetic, broad-spectrum aminoglycoside antibiotic. It is a 1-N-ethyl derivative of the natural antibiotic sisomycin produced by fermentation of Micromonospora inyoensis that has a similar mechanism of action to Gentamicin. Netilmicin was patented in 1973 by Schering-Plough. It can be used as an analytical standard for antimicrobial susceptibility testing or in studying aminoglycoside resistance.
    Netilmicin Sulfate is freely soluble in water.
    
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    Background
    
    Aminoglycosides target the 30S ribosomal subunit (specifically the 16S rRNA and S12 protein) resulting in an inability to read mRNA ultimately producing a faulty or nonexistent protein. Netilmicin also induces misreading of the mRNA template resulting in premature termination, eventually leading to death of the bacterial cells.
- Properties
  - CAS Number
    
    56391-57-2
    
    Molecular Formula
    
    C21H41N5O7 •2.5 H2SO4
    
    Molecular Weight
    
    720.78
    
    Appearance
    
    White or almost white powder
    
    Solubility
    
    Soluble in aqueous solution
    
    Other Properties
    
    Source: Semi-synthetic
    PH: 3.5-5.5
    Assay: (On Dried Basis): ≥595 μg/mg
    Loss on Drying: ≤15.0%
    Optical Rotation: +88° to +96°
    
    Storage
    
    2-8°C
    
    * For research use only
- Applications
  - Application Description
    
    Spectrum: Netilmicin Sulfate can be used against Gram-negative and some Gram-positive bacteria including some Gentamicin-resistant strains. Aminoglycosides are not active against anaerobic organisms.
    
    Microbiology Applications: Netilmicin Sulfate is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against Gram-positive and Gram-negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options. Representative MIC values include:
    Pseudomonas aeruginosa 0.5 µg/mL - 1 µg/mL
    Staphylococcus aureus 0.008 µg/mL - 4 µg/mL
    
    Eukaryotic Cell Culture Applications: Netilmicin Sulfate inhibited rat erythrocyte 6-phosphogluconate dehydrogenase (PGD) in vitro, with an IC50 of 0.963 mM (Cifci et al, 2002).
    Netilmicin was applied in vitro to human corneal epithelial cells (HCE-T) and human conjunctival epithelial cells at 0.08-5.0 mg/mL for 4 or 24 hours and cell proliferation and viability were assessed with the MTT assay, neutral red uptake, and bromo deoxy uridine incorporation. Researchers found Netilmicin did not induce any cell toxicity (Papa et al, 2004).
    Netilmicin was investigated for its interaction with melanin and how this process affects collagen biosynthesis in cultured human skin fibroblasts. It was found to form stable complexes with melanin. Additionally, it was found to strongly inhibit prolidase activity, which is an enzyme involved in collagen metabolism, and enzyme activity was inhibited by 80% when applied at 10 µM. When Melanin (100 µg/ml) was applied to netilmicin-treated cells, it restored the enzyme activity. The ability of Netilmicin to form stable complexes with melanin may prevent its toxicity on prolidase activity and collagen biosynthesis (Buszman et al, 2006).