CAS 1397-89-3

Amphotericin B

Beschreibung:

Amphotericin B ist ein polyenes Antimykotikum, das hauptsächlich zur Behandlung schwerer Pilzinfektionen eingesetzt wird, insbesondere solcher, die durch Candida- und Aspergillus-Arten verursacht werden. Es wird aus dem Bakterium Streptomyces nodosus gewonnen und ist bekannt für seine Fähigkeit, an Ergosterol zu binden, einen Schlüsselbestandteil der Pilzzellmembranen, was zu einer Störung der Zellmembran und letztendlich zum Zelltod führt. Amphotericin B zeichnet sich durch seine gelblich-braune Farbe aus und wird typischerweise intravenös verabreicht, da es eine geringe orale Bioverfügbarkeit aufweist. Es hat ein relativ hohes Molekulargewicht und ist in Dimethylsulfoxid (DMSO) und anderen organischen Lösungsmitteln löslich, aber schlecht in Wasser löslich. Das Medikament ist bekannt für seine potenziellen Nebenwirkungen, einschließlich Nephrotoxizität und infusionsbedingten Reaktionen, was eine sorgfältige Überwachung während der Behandlung erforderlich macht. Amphotericin B wird häufig in schweren Fällen eingesetzt, in denen andere antimykotische Behandlungen möglicherweise unwirksam sind, was es zu einer kritischen Option im Management invasiver Pilzinfektionen macht.

Formel: C₄₇H₇₃NO₁₇

InChl: InChI=1/C47H73NO17/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/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1

InChI Key: InChIKey=APKFDSVGJQXUKY-INPOYWNPSA-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\C=C\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]

Synonyme:

• (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-b-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-carboxylicacid
• (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-β-<span class="text-smallcaps">D</span>-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-β-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 acid
• 14,39-Dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid, 33-[(3-amino-3,6-dideoxy-β-<span class="text-smallcaps">D</span>-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-, (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-
• 14,39-Dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid, 33-[(3-amino-3,6-dideoxy-β-D-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-, (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-
• 14,39-Dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylicacid, 33-[(3-amino-3,6-dideoxy-b-D-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-,(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-
• Abelcet
• Abelecet
• AmBisome
• Ampho-Moronal
• Amphocin
• Amphozone
• Apothecon
• Fungilin
• Fungizona
• Fungizone
• Halizon
• Kalsome 10
• LNS-AmB
• Ns 718
• Nsc 527017
• amfotericina B
• amphotericine B
• Amphotericin B
• 17,37-octahydroxy-15,16,18-trimethyl-13-oxo-(1r-(1r*,3s*,5r*,6r*,9r*,11r*,15s*
• 14,39-dioxabicyclo(33.3.1)nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carbo
• AMPHOTERICIN B, STREPTOMYCES NODOSUS
• AMPHOTERICIN B, STREPTOMYCES SPECIES
• FUNGIZONE(R)
• AMPHOTERCIN B
• amphotericineb
• AMPHOTERICIN B SOLUBILIZED
• 33-((3-amino-3,6-dideoxy-beta-d-mannopyranosyl)oxy)-1,3,5,6,9,11,-xylicaci
• 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
• AMPHOTERICIN B, SOLUBLE
• amphomoronal
• ,16r*,17r*,18s*,19e,21e,23e,25e-27e,29e,31e,33r*,35s*,36r*,37s*))-

Amphotericin B

CAS: 1397-89-3

Amphotericin B is a macrocycle antibiotic first isolated from Streptomyces nodosus. Its antifungal activity is exerted by interacting with the fungal membrane, mainly ergosterol, and inducing pore formation. The increase in membrane permeability causes loss of ions and cell death. The C-2’ hydroxyl residue of the mycosamine carbohydrate moiety in the structure seems to have a major role in binding to ergosterol. It is used in cell culture to prevent growth of microbial contaminants, such as yeast and fungi. It is recommended by the WHO and CDC as an antifungal component for VTM at a concentration of 250ug/ml.

Formel: C₄₇H₇₃NO₁₇

Farbe und Form: Yellow Powder

Molekulargewicht: 924.08 g/mol

Ref: 3D-AA161113

Amphotericin B - Bio-X ™

CAS: 1397-89-3

Amphotericin B is a macrocycle antibiotic with very potent antifungal effects and resistance very rarely occurs. Amphotericin B is a polyene antifungal that binds to fungal cell membrane, i.e., ergosterol disrupts the membrane permeability leading to leakage of intracellular components. It is often used as an alternative therapy for leishmaniasis and to treat severe mycoses including: systemic Candida, Cryptococcus, blastomycosis, and histoplasmosis.

Formel: C₄₇H₇₃NO₁₇

Reinheit: Min. 75.0%

Farbe und Form: Powder

Molekulargewicht: 924.08 g/mol

Ref: 3D-AA15700

Amphotericin B

CAS: 1397-89-3

Formel: C₄₇H₇₃NO₁₇

Molekulargewicht: 924.09

Ref: ST-EA-CP-A134000

Amphotericin B

CAS: 1397-89-3

Formel: C₄₇H₇₃NO₁₇

Farbe und Form: Solid

Molekulargewicht: 924.1

Ref: BE-BePure-20337

Amphotericin B (~80%)

Kontrolliertes Produkt

CAS: 1397-89-3

Stability Hygroscopic
Applications Amphotericin B is a polypeptide antibiotic active against gram positive bacteria. It is antifungal.
References Asher, I.M., et al.: Anal. Profiles Drug Subs., 6, 1, (1977);

Formel: C₄₇H₇₃NO₁₇

Reinheit: ~80%

Farbe und Form: Neat

Molekulargewicht: 924.08

Ref: TR-A687800

Amphotericin B-[13C6]

CAS: 1397-89-3

Formel: C₄₇H₇₃NO₁₇

Farbe und Form: Solid

Molekulargewicht: 924.1

Ref: BE-MC-7991

Amphotericin B

CAS: 1397-89-3

Formel: C₄₇H₇₃NO₁₇

Farbe und Form: Solid

Molekulargewicht: 924.1

Ref: BE-RMCA196000

Amphotericin B

CAS: 1397-89-3

(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-methyltetrahydro-2H-pyran-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

Formel: C₄₇H₇₃NO₁₇

Reinheit: ≥750 μg/mg

Molekulargewicht: 924.08

Ref: IN-DG114239

Amphotericin B (AMT)

CAS: 1397-89-3

Formel: C₄₇H₇₃NO₁₇

Farbe und Form: Yellow to orange, Powder

Molekulargewicht: 924.09

Ref: SR-54713

Amphotericin B (AMT) Solution (250ug/ml) for cell culture, Endotoxin (BET) 1EU/ml

CAS: 1397-89-3

Formel: C₄₇H₇₃NO₁₇

Farbe und Form: Clear, Colourless, Liquid

Molekulargewicht:  924.09

Ref: SR-15875