Amphotericin B
[CAS# 1397-89-3]

Identification

• Classification: API >> Antibiotics >> Polyene
• Name: Amphotericin B
• Synonyms: 33-[(3-Amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-Dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid; Fungizone
• Molecular Formula: C₄₇H₇₃NO₁₇
• Molecular Weight: 924.08
• CAS Registry Number: 1397-89-3
• EC Number: 215-742-2
• SMILES: C[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(=O)O[C@H]([C@@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)C)O)N)O

Properties

• Solubility: <0.1 g/100 mL (21 °C, water)
• Density: 1.34±0.1 g/cm³
• Index of Refraction: 1.614, Calc.^*
• Boiling Point: 1140.4±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 643.5±34.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Respiratory sensitization	Resp. Sens.	1	H334
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Specific target organ toxicity - single exposure	STOT SE	3	H336

Discovery and Applications

Discovered in 1955 by researchers Rachel Fuller Brown and Elizabeth Lee Hazen at the New York State Department of Health, Amphotericin B emerged from their pioneering work in antifungal research. The breakthrough came through systematic screening of soil samples for potential antifungal activity. The compound was isolated from cultures of Streptomyces nodosus, a bacterium found in soil.

Amphotericin B remains a cornerstone in the treatment of severe systemic fungal infections. It is highly effective against a broad spectrum of fungal pathogens, including Candida and Aspergillus species. Its mechanism of action involves binding to ergosterol, a key component of fungal cell membranes, leading to disruption of membrane integrity and subsequent cell death. This makes it particularly useful in treating life-threatening fungal infections, such as invasive candidiasis and aspergillosis, especially in immunocompromised patients. Amphotericin B is also used in the treatment of fungal meningitis, a serious infection of the central nervous system caused by fungi such as Cryptococcus neoformans. Intrathecal or intraventricular administration of the drug can achieve therapeutic concentrations in the cerebrospinal fluid, providing effective treatment against fungal pathogens within the central nervous system. In certain high-risk patient populations, such as those undergoing bone marrow transplantation or receiving high-dose chemotherapy, prophylactic use of Amphotericin B may be employed to prevent invasive fungal infections. This proactive approach helps reduce the incidence of fungal infections, which can significantly impact patient outcomes in immunocompromised individuals. Amphotericin B is also used in the treatment of leishmaniasis, a parasitic disease caused by protozoa of the Leishmania genus.

References

1979. Interaction of the polyene antibiotic amphotericin B with phospholipid bilayer membranes: A circular dichroism study. Biochemical and Biophysical Research Communications.
DOI: 10.1016/0006-291x(79)91507-9

1979. Treatment of Experimental Naegleria Meningoencephalitis with a Combination of Amphotericin B and Rifamycin. Scandinavian Journal of Infectious Diseases.
DOI: 10.3109/inf.1979.11.issue-2.10

1979. Comparison of Microdilution and Broth Dilution Techniques for the Susceptibility Testing of Yeasts to 5-Fluorocytosine and Amphotericin B. Antimicrobial Agents and Chemotherapy.
DOI: 10.1128/aac.15.3.475