DT-Web

DB00681 - Amphotericin B


Identification
Name Amphotericin B
Accession Number DB00681 (APRD00797)
Type small molecule
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.
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 924.079
Groups approved
Monoisotopic Weight 923.487849915
Pharmacology
Indication Used to treat potentially life threatening fungal infections.
Mechanism of action Amphotericin B is fungistatic or fungicidal depending on the concentration obtained in body fluids and the susceptibility of the fungus. The drug acts by binding to sterols (ergosterol) in the cell membrane of susceptible fungi. This creates a transmembrane channel, and the resultant change in membrane permeability allowing leakage of intracellular components. Ergosterol, the principal sterol in the fungal cytoplasmic membrane, is the target site of action of amphotericin B and the azoles. Amphotericin B, a polyene, binds irreversibly to ergosterol, resulting in disruption of membrane integrity and ultimately cell death.
Absorption Bioavailability is 100% for intravenous infusion.
Protein binding Highly bound (>90%) to plasma proteins.
Biotransformation Exclusively renal
Route of elimination Not Available
Toxicity Oral, rat: LD50 = >5 gm/kg. Amphotericin B overdoses can result in cardio-respiratory arrest.
Affected organisms
  • Various Fungus Species
Interactions
Drug Interactions
Drug Mechanism of interaction
Colistimethate Amphotericin B may enhance the nephrotoxic effect of Colistimethate. Due to the potential for additive or synergistic nephrotoxicity between colistimethate and other nephrotoxic drugs, such as amphotericin B, this combination should be avoided whenever possible. If these agents must be used together, patients' renal function should be monitored closely.
Cyclosporine Monitor for nephrotoxicity
Tacrolimus Additive renal impairment may occur during concomitant therapy with Amphotericin B. Use caution during concomitant therapy.
Tobramycin Increased risk of nephrotoxicity
Food Interactions Not Available

Targets


Ergosterol, Candida albicans
Name Ergosterol, Candida albicans
Gene Name Not Available
Pharmacological action yes
Actions binder
References
  • Laniado-Laborin R, Cabrales-Vargas MN: Amphotericin B: side effects and toxicity. Rev Iberoam Micol. 2009 Dec 31;26(4):223-7. - Pubmed
  • Baginski M, Czub J: Amphotericin B and its new derivatives - mode of action. Curr Drug Metab. 2009 Jun;10(5):459-69. - Pubmed
  • Baginski M, Sternal K, Czub J, Borowski E: Molecular modelling of membrane activity of amphotericin B, a polyene macrolide antifungal antibiotic. Acta Biochim Pol. 2005;52(3):655-8. Epub 2005 Aug 5. - Pubmed
DTHybrid score Not Available

Predictions


Id Partner name Gene Name Score
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