Amphotericin B EP

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Amphotericin B, EP is a polyene antifungal or antimycotic compound derived from Streptomyces nodosus. Amphotericin B, EP is nearly insoluble in water but can be solubilized in sodium deoxycholate.

Amphotericin B, EP meets European Pharmacopoeia specifications.

Mechanism of Action
Amphotericin B associates with membrane sterols in mammalian and fungal cell membranes. Amphotericin B forms a pore in these membranes leading to essential ion leakage and ultimately, cell death.

Specification

CAS Number: 1397-89-3

Molecular Formula: C₄₇H₇₃NO₁₇

Molecular Weight: 924.08

Appearance: Yellow or Orange hygroscopic powder

Solubility
Insoluble: H2O, Ethanol
Soluble: Dimethyl sulfoxide, propylene glycol, slightly soluble in methanol

Source: Streptomyces nodosus

Absorbance: UV max: 362, 381 and 405nm
UV ratios:
 A362/A381 = 0.57-0.61
 A381/A405 = 0.87-0.93

Assay: (On Dried Basis): ≥750 IU/mg

Loss on Drying: ≤5.0%

Sulfated Ash: ≤3.0%

Impurities
Related Substances
- Impurity A (303 nm): ≤5.0%
- Any Other Impurity (303 nm): ≤1.0%
- Impurity B (383 nm): ≤4.0%
- Any Other Impurity (383 nm): ≤2.0%
- Total Impurities (303 nm and 383 nm): ≤15.0%

Identification: UV, IR, HPLC, and by an EP designed experiment

Spectrum
Amphotericin B is active against mammalian and fungal (molds and yeasts) cells. Amphotericin B is not toxic to bacteria due to their lack of sterols.

The following represents MIC susceptibility data for amphotericin B against common fungal pathogens:
• Candida albicans - 0.001 - 321 μg/mL
• Candida krusei - 0.001 - 16 μg/mL
• Coccidioides immitis - 0.0625 - 2 μg/mL
• Cryptococcus neoformans - 0.2 - 39 μg/mL
• Fusarium oxysporum - 0.75 - 125 μg/mL

Microbiology Applications
Amphotericin B is used as an antimycotic selective agent in several routinely used selective media formulations to inhibit the growth of background fungal growth.

Eukaryotic Cell Culture Applications
Amphotericin B can be used in eukaryotic cell culture to control or prevent fungal contamination. Amphotericin B can be toxic to cell lines at high concentrations and should not be used at concentrations greater than 2.50 µg/mL.

References

Rice, Louis B., and Mahmoud A. Ghannoum. "Antifungal Agents: Mode of Action, Mechanisms of Resistance, and Correlation of These Mechanisms with Bacterial Resistance." Clinical Microbiology Reviews (1999): 501-17. www.ncbi.gov. Oct. 1999. Web. 22 Aug. 2012.

Rice L.B. and Ghannoum M.A.. "Antifungal Agents: Mode of Action, Mechanisms of Resistance, and Correlation of These Mechanisms with Bacterial Resistance. Clinical Microbiology Reviews (1999): 501-17.

Brajtburg, J., W. G. Powderly, and G. Medoff. "Amphotericin B: Current Understanding of Mechanisms of Action." Antimicrobial Agents and Chemotherapy 34.2 (1990): 183-88. www.ncbi.gov. Web. 22 Aug. 2012.

Perez-de-Luque A., Cifuentes Z., Beckstead J.A., Sillero J.C., Avila C., Rubio J. and Ryan R.O.. Effect of amphotericin B nanodisks on plant fungal diseases. Volume 68, Issue 1, Article first published online: 24 Jun 2011.