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Amphotericin B

CAT: 0013-GTR19163317-03Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19163317-03Size:500 mg
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Description
Amphotericin B is a Lipid-based Polyene Antifungal and Polyene Antifungal. The chemical classification of amphotericin b is Polyenes. (In Vitro) :Amphotericin B administration is limited by infusion-related toxicity, including fever and chills, an effect postulated to result from proinflammatory cytokine production by innate immune cells. Amphotericin B induces signal transduction and inflammatory cytokine release from cells expressing TLR2 and CD14. Amphotericin B interacts with cholesterol, the major sterol of mammal membranes, thus limiting the usefulness of Amphotericin B due to its relatively high toxicity. Amphotericin B is dispersed as a pre-micellar or as a highly aggregated state in the subphase. Amphotericin B only kills unicellular Leishmania promastigotes (LPs) when aqueous pores permeable to small cations and anions are formed. Amphotericin B (0.1 mM) induces a polarization potential, indicating K+ leakage in KCl-loaded liposomes suspended in an iso-osmotic sucrose solution. Amphotericin B (0.05 mM) exhibits a nearly total collapse of the negative membrane potential, indicating Na+ entry into the cells. (In Vivo) :Amphotericin B results in prolonging the incubation time and decreasing PrPSc accumulation in the hamster scrapie model. Amphotericin B markedly reduces PrPSc levels in mice with transmissible subacute spongiform encephalopathies (TSSE) . Amphotericin B exerts a direct effect on Plasmodium falciparum and influences eryptosis of infected erythrocytes, parasitemia and hostsurvival in murine malaria. Amphotericin B tends to delay the increase of parasitemia and significantly delays host death plasmodium berghei-infected mice.
CAS Number
1397-89-3
Product Name Alternative
Abelcet | AmBisome | Amphocin | Ampho-Moronal | Amphozone
Field of Research
Pharmacology & Drug Discovery
Purity
>98% (HPLC)
Solubility
DMSO: 22 mg/mL (23.8 mM)
Smiles
O=C ([C@@H] ([C@] (O1) ([H]) C[C@@H] (O[C@@H]2O[C@H] (C) [C@@H] (O) [C@H] (N) [C@@H]2O) /C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H] (C) [C@@H] (O) [C@@H] (C) [C@H] (C) O3) [C@@H] (O) C[C@@]1 (O) C[C@@H] (O) C[C@@H] (O) [C@H] (O) CC[C@@H] (O) C[C@@H] (O) CC3=O) O
Molecular Formula
C47H73NO17
Molecular Weight
924.08
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
(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-methyltetrahydro-2H-pyran-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

Chemical Information

Amphotericin B

Amphotericin B is a macrolide antibiotic used to treat potentially life-threatening fungal infections. It has a role as an antiamoebic agent, an antiprotozoal drug and a bacterial metabolite. It is a macrolide antibiotic, a polyene antibiotic and an antibiotic antifungal drug.

CAS Number1397-89-3
PubChem CID5280965
IUPAC 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
Molecular FormulaC47H73NO17
Molecular Weight924.1
XLogP0
Topological Polar Surface Area320
Hydrogen Bond Donor Count12
Hydrogen Bond Acceptor Count18
Rotatable Bond Count3
Heavy Atom Count65
Formal Charge0
Complexity1670
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
InChI
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
InChIKey
APKFDSVGJQXUKY-INPOYWNPSA-N
Chemical Structure
2D Structure
2D structure of Amphotericin B
CAS: 1397-89-3
CID: 5280965
Formula: C47H73NO17
MW: 924.1
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight924.1
XLogP30
Hydrogen Bond Donor Count12
Hydrogen Bond Acceptor Count18
Rotatable Bond Count3
Exact Mass923.48784986
Monoisotopic Mass923.48784986
Topological Polar Surface Area320 Ų
Heavy Atom Count65
Formal Charge0
Complexity1670
Isotope Atom Count0
Defined Atom Stereocenter Count19
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count7
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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