amphotericin b
Amphotericin B is a polyene macrolide antibiotic characterized by a 23-membered lactone ring, multiple conjugated double bonds, and hydroxyl groups at positions C-1, C-3, and C-5. Its structure includes a long hydrophobic side chain and a glycosidic linkage to a hexose moiety, conferring amphipathic properties. As an API impurity, it arises as a major degradation byproduct during storage or synthesis of the parent antifungal agent. This compound serves as an HPLC reference standard for quantification in quality control assays.
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Molecular Formula
C47H73NO17
Molecular Weight
924.1000
CAS Number
1397-89-3
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PubChem CID
5280965 ↗
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
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Official Reference Standards
| Std | Catalog # | Quantity | Price |
|---|---|---|---|
| EP | Y0000005 ↗ | 100 MG | EUR 90.00 |
| EP | Y0001361 ↗ | 100 MG | EUR 90.00 |
| EP | Y0001014 ↗ | 10 MG | EUR 90.00 |
| USP | 1032007 ↗ | 125 mg | USD 226.00 |
📝 Synonyms
amphotericin b
1397-89-3
Amphotericine B
Amfotericina B
Halizon
Ampho-Moronal
Amphotericinum B
Fungizone
Amphocin
Amphotec
🔬 Chemical Identifiers
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=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
APKFDSVGJQXUKY-INPOYWNPSA-N
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