CAS 1397-89-3

Amphotericin B

Description:

Amphotericin B is a polyene antifungal agent primarily used to treat serious fungal infections, particularly those caused by Candida and Aspergillus species. It is derived from the bacterium Streptomyces nodosus and is known for its ability to bind to ergosterol, a key component of fungal cell membranes, leading to cell membrane disruption and ultimately cell death. Amphotericin B is characterized by its yellowish-brown color and is typically administered intravenously due to its poor oral bioavailability. It has a relatively high molecular weight and is soluble in dimethyl sulfoxide (DMSO) and other organic solvents, but poorly soluble in water. The drug is known for its potential side effects, including nephrotoxicity and infusion-related reactions, which necessitate careful monitoring during treatment. Amphotericin B is often used in severe cases where other antifungal treatments may be ineffective, making it a critical option in the management of invasive fungal infections.

Formula: C₄₇H₇₃NO₁₇

InChI: 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]

Synonyms:

• (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.

Formula: C₄₇H₇₃NO₁₇

Color and Shape: Yellow Powder

Molecular weight: 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.

Formula: C₄₇H₇₃NO₁₇

Purity: Min. 75.0%

Color and Shape: Powder

Molecular weight: 924.08 g/mol

Ref: 3D-AA15700

Amphotericin B

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Molecular weight: 924.09

Ref: ST-EA-CP-A134000

Amphotericin B

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Color and Shape: Solid

Molecular weight: 924.1

Ref: BE-BePure-20337

Amphotericin B (~80%)

Controlled Product

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);

Formula: C₄₇H₇₃NO₁₇

Purity: ~80%

Color and Shape: Neat

Molecular weight: 924.08

Ref: TR-A687800

Amphotericin B-[13C6]

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Color and Shape: Solid

Molecular weight: 924.1

Ref: BE-MC-7991

Amphotericin B

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Color and Shape: Solid

Molecular weight: 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

Formula: C₄₇H₇₃NO₁₇

Purity: ≥750 μg/mg

Molecular weight: 924.08

Ref: IN-DG114239

Amphotericin B (AMT)

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Color and Shape: Yellow to orange, Powder

Molecular weight: 924.09

Ref: SR-54713

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

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Color and Shape: Clear, Colourless, Liquid

Molecular weight:  924.09

Ref: SR-15875