CAS 1397-89-3

Amfotericina B

Descrizione:

Amfotericina B è un agente antifungino polieno utilizzato principalmente per trattare infezioni fungine gravi, in particolare quelle causate da specie di Candida e Aspergillus. È derivato dal batterio Streptomyces nodosus ed è noto per la sua capacità di legarsi all'ergosterolo, un componente chiave delle membrane cellulari fungine, portando alla rottura della membrana cellulare e, infine, alla morte cellulare. Amfotericina B è caratterizzato dal suo colore marrone-giallastro ed è tipicamente somministrato per via endovenosa a causa della sua scarsa biodisponibilità orale. Ha un peso molecolare relativamente alto ed è solubile in dimetilsolfossido (DMSO) e altri solventi organici, ma poco solubile in acqua. Il farmaco è noto per i suoi potenziali effetti collaterali, tra cui nefrotossicità e reazioni correlate all'infusione, il che richiede un attento monitoraggio durante il trattamento. Amfotericina B è spesso utilizzato in casi gravi in cui altri trattamenti antifungini possono essere inefficaci, rendendolo un'opzione critica nella gestione delle infezioni fungine invasive.

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]

Sinonimi:

• (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

Colore e forma: Yellow Powder

Peso molecolare: 924.08 g/mol

Ref: 3D-AA161113

Amphotericin B (~80%)

Prodotto controllato

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

Purezza: ~80%

Colore e forma: Neat

Peso molecolare: 924.08

Ref: TR-A687800

Amphotericin B (AMT)

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Colore e forma: Yellow to orange, Powder

Peso molecolare: 924.09

Ref: SR-54713

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

CAS: 1397-89-3

Formula: C₄₇H₇₃NO₁₇

Colore e forma: Clear, Colourless, Liquid

Peso molecolare:  924.09

Ref: SR-15875

Amphotericin B-13C6

CAS: 1397-89-3

Formula: C₄₇H₇₃O₁₇

Peso molecolare: 930.04

Ref: 4Z-A-137007