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, 250 &mu;g/mL in distilled water, sterile-filtered

CAS: 1397-89-3

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Sci

Ref: 02-J67049

Amphotericin B, Streptomyces nodosus

CAS: 1397-89-3

Amphotericin B, Streptomyces nodosus, 1397-89-3, is a polyene with antibiotic properties which alters cell membrane permeability, leading to lysis and cell death. Learn more.

Formula: C₄₇H₇₃NO₁₇

Molecular weight: 924.09

Ref: 02-J61491

AMPHOTERICIN B FOR PEAK IDENTIFICATION CRS

CAS: 1397-89-3

AMPHOTERICIN B FOR PEAK IDENTIFICATION CRS

Formula: C₄₇H₇₃NO₁₇

Molecular weight: 924.079

Ref: 41-Y0001014

AMPHOTERICIN B CRS

CAS: 1397-89-3

AMPHOTERICIN B CRS

Formula: C₄₇H₇₃NO₁₇

Molecular weight: 924.079

Ref: 41-Y0000005

AMPHOTERICIN B FOR MICROBIOLOGICAL ASSAY CRS

CAS: 1397-89-3

AMPHOTERICIN B FOR MICROBIOLOGICAL ASSAY CRS

Formula: C₄₇H₇₃NO₁₇

Molecular weight: 924.079

Ref: 41-Y0001361

SECOND INTERNATIONAL STANDARD FOR AMPHOTERICIN B

CAS: 1397-89-3

SECOND INTERNATIONAL STANDARD FOR AMPHOTERICIN B

Formula: C₄₇H₇₃NO₁₇

Molecular weight: 924.079

Ref: 41-ISA_29078

AMPHOTERICIN B RS

CAS: 1397-89-3

AMPHOTERICIN B RS

Formula: C₄₇H₇₃NO₁₇

Molecular weight: 924.079

Ref: 41-ICRS0210

Amphotericin B

CAS: 1397-89-3

Antibiotics nesoi

Formula: C₄₇H₇₃NO₁₇

Color and Shape: Yellow Orange Powder

Molecular weight: 923.48785

Ref: 45-1032007

Amphotericin B

CAS: 1397-89-3

Amphotericin B (NSC-527017) is a polyene antifungal agent with broad-spectrum activity against many fungal species.

Formula: C₄₇H₇₃NO₁₇

Purity: 99.75% - ≥98%

Color and Shape: Deep Yellow Prisms Or Needles From N N-Dimethylformamide Physical Description Bright Yellow Powder (Ntp 1992)

Molecular weight: 924.08

Ref: TM-T1067

AmphotericinB

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Purity: 95%

Color and Shape: Solid

Molecular weight: 924.0790

Ref: IN-DA00ILH6

Amphotericin B

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Color and Shape: Yellow Solid

Molecular weight: 924.09

Ref: 4Z-A-137002

Amphotericin B

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Purity: ≥ 750μg/mg (C47H73NO17, dried basis)

Color and Shape: Yellow to dark yellow or orange powder

Molecular weight: 924.10

Ref: 7W-GA8986

Amphotericin B, Ph. Eur. grade

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Purity: ≤ 2.0% (at 383nm)

Color and Shape: Yellow or orange powder

Molecular weight: 924.10

Ref: 7W-GA2492

Amphotericin B

CAS: 1397-89-3

Amphotericin B

Formula: C₄₇H₇₃NO₁₇

Color and Shape: yellow powder

Molecular weight: 924.07902g/mol

Ref: 54-BIA0103

Amphotericin B

CAS: 1397-89-3

Amphotericin B

Purity: ≥98%

Molecular weight: 924.08g/mol

Ref: 54-BUP15128

Amphotericin B

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Purity: >80.0%(HPLC)

Color and Shape: White to Light orange to Yellow powder to crystal

Molecular weight: 924.09

Ref: 3B-A2114

Amphotericin B

Controlled Product

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Color and Shape: Neat

Molecular weight: 924.08

Ref: 04-C10243050

Amphotericin B (85%)

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Purity: 85%

Color and Shape: Yellow

Molecular weight: 924.08

Ref: TR-A634250

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, Antibiotic for Culture Media Use Only

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

Purity: Min. 80.0 Area-%

Molecular weight: 924.08 g/mol

Ref: 3D-A-7680