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Product Description
Mechanism of action
Amphotericin B binds ergosterol in fungal cell membranes, forming transmembrane pores that cause leakage of intracellular ions (K⁺, Mg²⁺) and metabolites. This leads to osmotic imbalance and fungal cell death. Amphotericin B also generates oxidative damage through reactive oxygen species.
Benefits and advantages
Remains the reference gold‑standard antifungal for severe systemic infections. In research it is used to model fungicidal membrane disruption, sterol-binding kinetics and liposomal drug delivery systems.
Side effects and risks
Severe nephrotoxicity, electrolyte disturbances, infusion reactions, fever and chills. Requires cytotoxic-grade handling with protective filtration systems.
Datasheet
| Molecular Formula | C47H73NO17 |
|---|---|
| Molecular Weight | 924.1 g/mol |
| CAS Number | 1397-89-3 |
| Storage Condition | Conventional amphotericin B powder for injection should be stored at 2-8 °C. Reconstituted colloidal dispersions of conventional amphotericin B should be protected from light and are stable for 24 hours at room temperature or 1 week when refrigerated at 2-8 °C. Although the manufacturers state that reconstituted dispersions or IV infusions of amphotericin B should be protected from light during administration, potency is unaffected if the infusion is exposed to light for less than 8-24 hours. |
| Solubility | less than 1 mg/mL at 70 °F (NTP, 1992) |
| Purity | Purity information is available upon request (COA). |
| Synonym | amphotericin b; 1397-89-3; Amphotericine B; Amfotericina B; Halizon |
| IUPAC/Chemical Name | (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]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 |
| InChl Key | APKFDSVGJQXUKY-INPOYWNPSA-N |
| InChl Code | InChI=1S/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1 |
| References |
3D Conformer.
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