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Structure Database (LMSD)

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Common Name

Amphotericin B

Systematic Name

Synonyms

LM ID

LMPK06000002

Formula

C₄₇H₇₃NO₁₇

Exact Mass

Calculate m/z

923.487855

Status

Curated

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Classification

Biological Context

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

This information has been provided by Cayman Chemical

References

1. 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).

2. 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).

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

4. 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).

String Representations

InChiKey (Click to copy)

APKFDSVGJQXUKY-INPOYWNPSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

[C@]12([H])C[C@H](C=CC=CC=CC=CC=CC=CC=C[C@@H]([C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@@](C[C@H](O)[C@H]1C(=O)O)(O)O2)C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](N)[C@@H]1O)C