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46006

Supelco

Amphotericin B trihydrate

VETRANAL®, analytical standard

Empirical Formula (Hill Notation):
C47H73NO17 · 3H2O
Número CAS:
Peso molecular:
978.12
Número EC:
Número MDL:
ID de substância PubChem:
NACRES:
NA.24

grau

analytical standard

Nível de qualidade

200

linha de produto

VETRANAL®

prazo de validade

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

clinical testing

formato

neat

temperatura de armazenamento

2-8°C

SMILES string

O[C@]1(C[C@H](O)[C@@H](C(O)=O)[C@@]2([H])O1)C[C@@H](O)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)CC(O[C@H]([C@@H]([C@@H]([C@@H](C)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@H](N)[C@@H]3O)C2)O)C)C)=O.O.O.O

InChI

1S/C47H73NO17.3H2O/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);3*1H2/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

QEWGLCMWTBNETQ-KCPNHEJKSA-N

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Aplicação

Amphotericin B is a polyene antifungal antibiotic from Streptomyce sp. It has a high affinity for sterols, especially ergosterols, of both fungal and bacterial cell membranes. Normal usage in maintenance of antifungal cell cultures is 2.5 mg/L with penicillin and streptomycin used in the medium.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Ações bioquímicas/fisiológicas

Mode of Action: Amphotericin B binds to sterols, forming channels in the membrane, and causing small molecules to leak out.

Antimicrobial Spectrum: The product is most effective against fungi and yeast.

Atenção

Amphotericin B remains active for 3 days in culture at 37°C. At -20°C, and with protection from air and light, the product remains active for 5 years.

Nota de preparo

Amphotericin B is insoluble in water at pH 6 to 7, but soluble in water at pH 2 or 11. It is soluble in DMSO (30-40 mg/mL) and in dimethylformamide (2-4 mg/mL). Aqueous solutions cannot be sterile filtered due to poor solubility.

Informações legais

VETRANAL is a registered trademark of Sigma-Aldrich Chemie GmbH

Pictogramas

Health hazard

Palavra indicadora

Danger

Frases de perigo

Declarações de precaução

Classificações de perigo

STOT RE 1

Código de classe de armazenamento

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Ponto de fulgor (ºF)

Not applicable

Ponto de fulgor (ºC)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Certificado de análise

Certificado de origem

Rania Hamdy et al.
Molecules (Basel, Switzerland), 25(6) (2020-03-28)
Candida is the most common fungal class, causing both superficial and invasive diseases in humans. Although Candida albicans is the most common cause of fungal infections in humans, C. auris is a new emergent serious pathogen causing complications similar to
Dima Youssef et al.
Tennessee medicine : journal of the Tennessee Medical Association, 106(3), 37-39 (2013-04-03)
Blastomycosis rarely presents in pregnancy. Pregnancy is a state of partial immunodeficiency that predisposes to blastomyces infection, especially in endemic areas. Blastomycosis in pregnancy has been reported in a few female patients and their offspring. We are reporting a 32-year-old
Benoit Pilmis et al.
Medecine sciences : M/S, 29 Spec No 1, 25-30 (2013-05-15)
Mucormycosis is a life-threatening invasive fungal infection that arises among immunocompromised patients (haematological malignancies, solid organ transplantation, diabetes mellitus). The most frequent sites of infection are pulmonary, rhinocerebral, cutaneous and disseminated. Reversal of the underlying conditions is mandatory for controlling
Bao Zhang et al.
Biochimica et biophysica acta, 1828(9), 2230-2237 (2013-06-13)
Bacillomycin L, a natural iturinic lipopeptide produced by Bacillus amyloliquefaciens, is characterized by strong antifungal activities against a variety of agronomically important filamentous fungi including Rhizoctonia solani Kühn. Prior to this study, the role of membrane permeabilization in the antimicrobial
Tzu-Sen Yang et al.
Biochimica et biophysica acta, 1828(8), 1794-1801 (2013-04-09)
Recently, the structure-function relationships between amphotericin B (AmB) and ergosterol have been solved using synthetic techniques that require a mycosamine-mediated direct binding interaction between AmB and ergosterol to form AmB ion channels. However, studies to directly probe the AmB-induced membrane

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