Amphotericin B
(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-azaniumyl-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-carboxylate
Grundinformationen
- CAS
1397-89-3- Standard-SMILES
C[C@@H]1[C@H](O)[C@@H](C)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H]([NH3+])[C@@H]2O)C[C@@H]2O[C@](O)(C[C@@H](O)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)CC(=O)O[C@H]1C)C[C@H](O)[C@H]2C(=O)[O-]- InChIKey
APKFDSVGJQXUKY-INPOYWNPSA-N- Summenformel
- C47H73NO17
- Durchschnittliche Molmasse
- 924,1 g/mol
- Monoisotopische Masse
- 923,48784986
Überblick
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.
Namen und Bezeichner
- Bevorzugter 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-azaniumyl-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-carboxylate
- IUPAC
- (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-azaniumyl-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-carboxylate
- Lokaler Name
- Amphotericin B
- Englischer Name
- Amphotericin B
- Summenformel
- C47H73NO17
- Molmasse
- 924.08
Namen und Synonyme
AMPHOTERICINAMBISOMEFUNGIZONEABELCETfungilinApotheconAMphotericin B (Abelcet)33-[(3-amino-3,6-dideoxy-beta-d-mannopyranosyl)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(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(3-Amino-3,6-dideoxy-.beta.-D-mannopyranosyl)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 acidns718
Datenbank-Bezeichner
- CAS
1397-89-3- PubChem CID
- 91819969
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,6
- Polarare Oberfläche (TPSA)
- 324 Ų
- H-Brücken-Donoren
- 11
- H-Brücken-Akzeptoren
- 17
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 65
- Formalladung
- 0
- Komplexität
- 1.660
Experimentelle und physikochemische Eigenschaften
LipidsPolyketides [PK] -> Polyenes [PK06]
LogP0.8
Solubility8.19e-02 g/L
Melting Point170.0 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 170 °C · >170°C
- Siedepunkt
- 804.34 °C · 804.34°C (rough estimate)
- Dichte
- 1.34 · 1.34
- Brechungsindex
- 1.528 · 1.5280 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 20 mg/mL · sterile water: 20 mg/mL as a stock solution. Stock solutions should be stored at −20°C. Stable at 37°C for 3 days.
- Aggregatzustand
- powder
- pka
- 5.7 · pKa ~5.7(DMF/H2O) (Uncertain)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- F
- 8-10-21
- wgk
- 3
- ridadr
- UN 1759 8/PG 3
- hs_code
- 29419090
- RTECS-Nr.
- BU2625000
- risk_code
- 36/37/38-22-40-23/24/25
- Toxizität
- LD50 in mice (mg/kg): 88 i.p., 4 i.v. (Keim)
- hazard_code
- C,Xi,Xn,T
- safety_code
- 26-36/37/39-45-36-60-37
- hazard_class
- 6.1(b)
- packing_group
- III
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Giftige Stoffe Daten
- 1397-89-3(Hazardous Substances Data)
- Hazard Classifications
- STOT RE 1
Chemie und Industrie
Pharmakologische Informationen
Protein BindingHighly bound (>90%) to plasma proteins.
Pharmacodynamics
Amphotericin B shows a high order of <i>in vitro</i> activity against many species of fungi. <i>Histoplasma capsulatum</i>, <i>Coccidioides immitis</i>, <i>Candida species</i>, <i>Blastomyces dermatitidis</i>, <i>Rhodotorula</i>, <i>Cryptococcus neoformans</i>, <i>Sporothrix schenckii</i>, <i>Mucor mucedo</i>, and <i>Aspergillus fumigatus</i> are all inhibited by concentrations of amphotericin B ranging from 0.03 to 1.0 mcg/mL <i>in vitro</i>. While <i>Candida albicans</i> is generally quite susceptible to amphotericin B, non-<i>albicans</i> species may be less susceptible. <i>Pseudallescheria boydii</i> and <i>Fusarium</i> sp. are often resistant to amphotericin B. The antibiotic is without effect on bacteria, rickettsiae, and viruses.
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.
Biological Half-LifeAn elimination half-life of approximately 15 days follows an initial plasma half-life of about 24 hours.
Metabolism/MetabolitesExclusively renal
Absorption, Distribution and Excretion
Bioavailability is 100% for intravenous infusion.
39 +/- 22 mL/hr/kg [febrile neutropenic cancer and bone marrow transplant patients receiving infusion of 1 mg/kg/day at Day 1]
Anwendungen
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