Amphotericin B

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. 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. 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.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-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. 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: DMSO: 2 mg/ml, DMSO:PBS(pH7.2) (1:1): 0.5 mg/ml. lambdamax: 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.