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CAS 1405-32-9

:

amphotericin A

Description:
Amphotericin A, with the CAS number 1405-32-9, is a polyene macrolide antibiotic primarily derived from the fermentation of Streptomyces nodosus. It is known for its antifungal properties, particularly effective against a range of fungal pathogens, including Candida and Aspergillus species. The compound exhibits a complex structure characterized by a large lactone ring and multiple conjugated double bonds, which contribute to its ability to bind to ergosterol, a key component of fungal cell membranes. This interaction disrupts membrane integrity, leading to cell death. Amphotericin A is typically administered intravenously due to its poor oral bioavailability and is often used in the treatment of serious systemic fungal infections. While effective, it is associated with significant side effects, including nephrotoxicity and infusion-related reactions, necessitating careful monitoring during treatment. Its use has been somewhat supplanted by newer antifungal agents with improved safety profiles, but it remains a critical option in severe cases where other treatments may fail.
Formula:C47H75NO17
InChI:InChI=1/C47H75NO17/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/h5-6,8,10-18,27-38,40-44,46,49-54,56-58,61H,7,9,19-26,48H2,1-4H3,(H,59,60)/b6-5+,10-8-,13-11-,14-12+,17-15+,18-16+
InChI key:InChIKey=QGGFZZLFKABGNL-MOISJGEISA-N
SMILES:C(O)(=O)[C@H]1[C@]2(O[C@@](O)(C[C@@H]1O)C[C@@H](O)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)CC(=O)O[C@@H](C)[C@H](C)[C@H](O)[C@@H](C)\C=C\C=C\CC\C=C\C=C\C=C\C=C\[C@H](O[C@H]3[C@@H](O)[C@@H](N)[C@H](O)[C@@H](C)O3)C2)[H]
Synonyms:
  • 14,39-Dioxabicyclo[33.3.1]nonatriacontane, amphotericin B deriv.
  • 28,29-Dihydroamphotericin B
  • 33-[(3-Amino-3,6-Dideoxyhexopyranosyl)Oxy]-1,3,5,6,9,11,17,37-Octahydroxy-15,16,18-Trimethyl-13-Oxo-14,39-Dioxabicyclo[33.3.1]Nonatriaconta-19,21,25,27,29,31-Hexaene-36-Carboxylic Acid
  • Amphotericin B, 28,29-dihydro-
  • Amphotericin A
  • Amphotericin B Impurit A:Amphotericin A (28, 29-Dihydro-Amphotericin B)
  • Amphotericin B EP Impurity A
  • Amphotericin A (28, 29-Dihydro-Amphotericin B)
  • (4E,6E,8E,10E,14E,16E)-3-(4-amino-3,5-dihydroxy-6-methyloxan-2-yl)oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,14,16-hexaene-38-carboxylic acid
  • Amphotericin B Impurity A
  • Amphotericin B Impurity 1 (Amphotericin A)(28, 29-Dihydro-Amphotericin B)
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