Erythromycin

- Overview
  - Erythromycin is a broad-spectrum macrolide antibiotic derived from Saccharopolyspora erythraea (formerly Streptomyces erythraeus) that inhibits bacterial protein synthesis. It is composed largely of Erythromycin A, with small amounts of Erythromycin B and C. It is typically used at a concentration of 100 mg/L. Erythromycin is soluble in ethanol and 2M HCl but sparingly soluble in water.
    
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    Background
    
    Macrolide antibiotics inhibit bacterial growth by targeting the 50S ribosomal subunit preventing peptide bond formation and translocation during protein synthesis. Resistance to Erythromycin is commonly attributed to mutations in 50S rRNA preventing erythromycin binding allowing the cell to synthesize proteins free of error.
- Properties
  - CAS Number
    
    114-07-8
    
    Molecular Formula
    
    C37H67NO13
    
    Molecular Weight
    
    733.93
    
    Appearance
    
    White powder
    
    Solubility
    
    Ethanol: Freely soluble
    Water: Sparingly soluble (2 mg/mL)
    Note: Solubility decreases with increasing temperature.
    
    Other Properties
    
    Source: Biosynthetic: Saccharopolyspora erythraea (formerly Streptomyces erythraeus).
    Water Content (Karl Fischer): ≤10.0%
    Assay: (On Dried Basis): 85-100.5%
    Melting Point: 135-140°C
    Optical Rotation: -71° to -78°
    
    Storage
    
    <30°C
    
    * For research use only
- Applications
  - Application Description
    
    Spectrum: Erythromycin is a broad-spectrum antibiotic targeting Gram-negative and Gram-positive bacteria. It is also effective against Mycoplasma, Mycobacteria, and spirochetes.
    
    Microbiology Applications: Erythromycin is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against Gram-positive, Gram-negative, and Mycoplasma species. Medical microbiologists use AST results to recommend antibiotic treatment options. Representative MIC values include: Mycoplasma pneumoniae 0.0019 µg/mL – 0.0078 µg/mL Legionella pneumophila 0.008 µg/mL – 1 µg/mL Plant Biology Applications: Erythromycin has been used in combination with nystatin and streptomycin for eliminating contaminants in rubber (Hevea brasiliensis) tissue culture (Leiffert et al, 1991).
    
    Eukaryotic Cell Culture Applications: There is growing evidence that Erythromycin has anti-inflammatory properties and can be used to ameliorate airway inflammation. Using adult human T-cell leukemic cell line (Jurkat; clone E6-1), researchers found that Erythromycin could inhibit cytokine gene expression (specifically IL-8 gene) in T-cells and this mechanism is at the level of transcriptional regulation (Aoki and Kao, 1999). Erythromycin A is a potent stimulator of gastrointestinal motor activity. In vitro studies suggest that it mimics motilin, a peptide that stimulates motor activity in human and rabbit cells via smooth muscle receptors (Peeters et al, 1989). The anti-inflammatory action of Erythromycin was evaluated by looking at isolated neutrophils from human blood. When Erythromycin was applied, it shortened neutrophil survival in a dose-dependent way, with maximum effect at 10 mg/ml and above. It shortens neutrophil survival in part through elevating cAMP (cyclic AMP) levels. The result was accelerated apoptosis. Apoptosis may limit tissue injury by marking senescent neutrophils for phagocytosis and degradation by macrophages and by inhibiting the capacity of neutrophils to make injurious responses to inflammatory mediators (Aoshiba et al, 1995).
    
    Cancer Applications: HERG (Human Ether-a-go-go Related Gene) may serve as a molecular marker and modulating target for individualized cancer therapy. Erythromycin, active as modulator and a HERG K+ channel blocker, suppressed the growth of various cancer cells and the potency was correlated with HERG expression levels. Erythromycin also enhanced the G2/M arrest induced by vincristine in HT-29 cells (Chen et al, 2005).