An antifungal macrolide
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Amphotericin B

Item No. 11636

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(3-amino-3,6-dideoxy-β-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
CAS Number
1397-89-3
Synonyms
  • LNS-AmB
  • NSC 527017
Molecular Formula
C47H73NO17
Formula Weight
924.1
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 2 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/ml
λmax
227, 283, 346, 364, 383,407 nm
SMILES
O=C1O[C@@H](C)[C@H](C)[C@H](O)[C@@H](C)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](O[C@]2([H])O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)C[C@@](O3)([H])[C@H](C(O)=O)[C@@H](O)C[C@@]3(O)C[C@@H](O)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)C1
InChi 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/h5-18,27-38,40-44,46,49-54,56-58,6
InChi Key
APKFDSVGJQXUKY-INPOYWNPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 mg

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    Product Description

    Amphotericin B is a classic antifungal polyene macrolide that has been used in the treatment of systemic fungal infections, primarily caused by C. albicans, A. fumigatus, and parasitic L. protozoans, as well as in tissue culture to prevent fungi from contaminating cell cultures.1,2,3 Amphotericin B binds with ergosterol, the main component of fungal cell membranes, forming a transmembrane channel that results in altered plasma membrane permeability and leakage of vital cytoplasmic components, such as K+, ultimately inducing cell death.4 Because prolonged use of amphotericin B is associated with infusion-related events and nephrotoxicity, lipid-based formulations have been devised for more favorable clinical relevance.1,2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Miceli, M.H., and Chandrasekar, P. Safety and efficacy of liposomal amphotericinB for the empirical therapy of invasive fungalinfections in immunocompromised patients. Infect. Drug. Resist. 5, 9-16 (2012).

    2. Wasan, K.M., Wasan, E.K., Gershkovich, P., et al. Highly effective oral amphotericin B formulation against murine visceral leishmaniasis. J. Infect. Dis. 200, 357-360 (2009).

    3. Radomski, N., Cambau, E., Moulin, L., et al. Comparison of culture methods for isolation of nontuberculous mycobacteria from surface waters. Appl. Environ. Microbiol. 76(11), 3514-3520 (2010).

    4. Ogita, A., Fujita, K.i., and Tanaka, T. Enhancing effects on vacuole-targeting fungicidal activity of amphotericin B. Front. Microbiol. 3, 100 (2012).

    Product Citations

    Kowalski, C.H., Morelli, K.A., Schultz, D., et al. Fungal biofilm architecture produces hypoxic microenvironments that drive antifungal resistance. Proc. Natl. Acad. Sci. USA 117(36), 22473-22483 (2020).