Amphotericin B

• Catalog No.: DB00681
• CAS Number: 1397-89-3
• M. F.: C47H73NO17
• M. W.: 924.07902

SYNONYMS

• 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
• IUPAC Traditional name: amphotericin B
• Brand Name: Amphozone; ABLC; Ampho-Moronal; Fungisone; AmB; Abelcet; AmBisome; Amphocin; Amphotec; Amphotericin; Fungilin; Fungizone Intravenous; Mysteclin-F; Tegopen; Fungizone; HSDB 3008 IAB; Halizon; IAB; LNS-AmB; SinuNase
• Synonyms: AMPH-B; Amphortericin B; Amphotericine B; Liposomal Amphotericin B; amphotericin B

DATABASE IDS

• PubChem CID: 5280965
• PubChem SID: 46505473
• CAS Number: 1397-89-3

PROPERTIES

• Hydrophobicity(logP): 0.8
• Solubility: 750 mg/L

DETAILS

Description (English)

• Drug Groups: approved; investigational
• Description: Amphotericin B shows a high order of in vitro activity against many species of fungi. Histoplasma capsulatum, Coccidioides immitis, Candida species, Blastomyces dermatitidis, Rhodotorula, Cryptococcus neoformans, Sporothrix schenckii, Mucor mucedo, and Aspergillus fumigatus are all inhibited by concentrations of amphotericin B ranging from 0.03 to 1.0 mcg/mL in vitro. While Candida albicans is generally quite susceptible to amphotericin B, non-albicans species may be less susceptible. Pseudallescheria boydii and Fusarium sp. are often resistant to amphotericin B. The antibiotic is without effect on bacteria, rickettsiae, and viruses.
• Indication: Used to treat potentially life threatening fungal infections.
• Pharmacology: Amphotericin B shows a high order of in vitro activity against many species of fungi. Histoplasma capsulatum, Coccidioides immitis, Candida species, Blastomyces dermatitidis, Rhodotorula, Cryptococcus neoformans, Sporothrix schenckii, Mucor mucedo, and Aspergillus fumigatus are all inhibited by concentrations of amphotericin B ranging from 0.03 to 1.0 mcg/mL in vitro. While Candida albicans is generally quite susceptible to amphotericin B, non-albicans species may be less susceptible. Pseudallescheria boydii and Fusarium sp. are often resistant to amphotericin B. The antibiotic is without effect on bacteria, rickettsiae, and viruses.
• Toxicity: Oral, rat: LD₅₀ = >5 gm/kg. Amphotericin B overdoses can result in cardio-respiratory arrest.
• Affected Organisms: Various Fungus Species
• Biotransformation: Exclusively renal
• Absorption: Bioavailability is 100% for intravenous infusion.
• Half Life: An elimination half-life of approximately 15 days follows an initial plasma half-life of about 24 hours.
• Protein Binding: Highly bound (>90%) to plasma proteins.
• Clearance: * 39 +/- 22 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 1 mg/kg/day at Day 1]; * 17 +/- 6 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 1 mg/kg/day 3-20 days later]; * 51 +/- 44 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 2.5 mg/kg/day at Day 1]; * 22 +/- 15 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 2.5 mg/kg/day 3-20 days later]; * 21 +/- 14 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 5 mg/kg/day at Day 1]; * 11 +/- 6 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 5 mg/kg/day 3-20 days later]
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