Amphotericin B
(1S,3R,4E,6E,8E,10E,12E,14E,16E,18S,19R,20S,21S,25R,27S,28S,31S,33S,35R,37S,38R)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-19,25,27,28,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-38-carboxylic acid
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](N)[C@@H]2O)C[C@@H]2O[C@](O)(C[C@@H](O)C[C@@H](O)CC[C@H](O)[C@@H](O)C[C@@H](O)CC(=O)O[C@H]1C)C[C@H](O)[C@H]2C(=O)O- InChIKey
QPVXKIMLGZQSRP-GJTMZYOUSA-N- Summenformel
- C47H73NO17
- Durchschnittliche Molmasse
- 924,1 g/mol
- Monoisotopische Masse
- 923,48784986
Überblick
AmBiosone is an aminoglycoside.
Namen und Bezeichner
- Bevorzugter Name
- (1S,3R,4E,6E,8E,10E,12E,14E,16E,18S,19R,20S,21S,25R,27S,28S,31S,33S,35R,37S,38R)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-19,25,27,28,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-38-carboxylic acid
- IUPAC
- (1R,3S,5S,8S,9S,11R,15S,16S,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-1,3,5,8,9,11,17,37-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
- Lokaler Name
- Amphotericin B
- Englischer Name
- Amphotericin B
- Summenformel
- C47H73NO17
- Molmasse
- 924.08
Namen und Synonyme
AmBiosone(1S,3R,4E,6E,8E,10E,12E,14E,16E,18S,19R,20S,21S,25R,27S,28S,31S,33S,35R,37S,38R)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-19,25,27,28,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-38-carboxylic acidAmB/LIPOSOMALNebulisex Ambisome (TM)Amphotericin B & NyotranCHEBI:230189Nebulised Liposomal Amphotericin BNS-718Amphotericin B & Nyotran(Liposomal Nystatin)Lipid nanosphere that incorporates amphotericin BRibbon form of lipid-stabilized amphotericin B aggregatesColloidal dispersion of cholesteryl sulfate and amphotericin B
Weitere Namen anzeigen
AMPHOTERICINAMBISOMEFUNGIZONEABELCET
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0
- Polarare Oberfläche (TPSA)
- 320 Ų
- H-Brücken-Donoren
- 12
- H-Brücken-Akzeptoren
- 18
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 65
- Formalladung
- 0
- Komplexität
- 1.670
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)
- Farbe
- yellow
- Wasserlöslichkeit
- 0.1 g/100 · <0.1 g/100 mL at 21 ºC
- Merck
- 13 · 13,590
- BRN
- 78342 · 78342
- Stabilität
- Stable, but may be light sensitive. Incompatible with strong oxidizing agents.
- InChIKey
- APKFDSVGJQXUKY-INPOYWNPSA-N
- CAS Datenbank
- 1397 · 1397-89-3(CAS DataBase Reference)
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
Anwendungen
VerwendenAmphotericin B is heptaene polyene antifungal originally discovered as a metabolite of Streptomyces nodosus in 1956. Amphotericin B acts by binding sterols in the cell membrane leading to the formation of transmembrane channels and subsequent ion leakage. Amphotericin B is poorly water soluble so has been developed for therapeutic use as a complex with desoxylate or in liposomes to improve bioavailability. Amphotericin B is widely used as a research reagent in diverse applications with over 15,000 literature citations.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Ergänzende Hinweise
DefinitionChEBI: Amphotericin B is a macrolide antibiotic used to treat potentially life-threatening fungal infections.
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