Nystatin – Properties, Uses, and Mechanism
Properties:
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Melting point: >155?°C (decomposition)
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Specific rotation:
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D25 -10° (glacial acetic acid)
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+21° (pyridine)
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+12° (DMF)
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-7° (0.1?N HCl in methanol)
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Storage conditions: -20?°C
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Solubility: Insoluble in water
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Physical form: Suspension
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Acidity (pKa): 5.72 (MeOH/2-methoxyethanol/H2O) (uncertain); 8.64 (uncertain)
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Color: Viscous yellow
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Odor: Grain-like odor
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Biological source: Streptomyces noursei
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Water solubility: 0.36?g/L at 24?°C
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Merck: 13,6770
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Specific activity: ≥4,400?USP units/mg
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BCS Class: 3
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InChIKey: VXWFKTGGEJLHPP-OQMKPJEFSA-N
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CAS Number: 1400-61-9
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EPA Chemical Info: Nystatin (1400-61-9)
Pharmacological Class: Polyene Antifungal
Uses and Mechanism of Action:
Nystatin is a polyene antifungal antibiotic with a conjugated polyene macrolide structure. It inhibits fungal activity but does not affect bacteria. Its mechanism involves binding to sterols (primarily ergosterol) in fungal cell membranes, altering membrane permeability and causing leakage of essential cellular contents, which results in fungal cell death.
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Applications:
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Prevention of contamination in cell cultures.
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Induction of cytokines such as interleukin (IL)-1, IL-8, and TLR2 expression in THP-1 cells, stimulating tumor necrosis factor-α (TNF-α) secretion.
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Used as a pore-forming agent targeting fungal membranes (ergosterol-binding) and creating nystatin/ergosterol ion channels in lipid bilayers.
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Nystatin is primarily employed in laboratory, clinical, and biotechnological settings as an antifungal and membrane-active agent.