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46006

Supelco

Amphotericin B trihydrate

VETRANAL®, analytical standard

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About This Item

Empirical Formula (Hill Notation):
C47H73NO17 · 3H2O
CAS Number:
1397-89-3
Molecular Weight:
978.12
EC Number:
215-742-2
MDL number:
MFCD25541905
UNSPSC Code:
41116107
PubChem Substance ID:
329757050
NACRES:
NA.24

grade

analytical standard

Quality Level

200

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

clinical testing

format

neat

Storage temp.

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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Application

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.

Biochem/physiol Actions

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.

Caution

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.

Preparation Note

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.

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H372

Hazard Classifications

STOT RE 1

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBW5196

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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
Afaq Ahmad Khan et al.
Journal of the Indian Medical Association, 110(7), 499-500 (2013-03-26)
Non-Hodgkin's lymphoma (NHL) is predominantly a disease of lymph nodes, but extranodal involvement is not very uncommon. Palatal involvement by NHL is rare. Mucormycosis is a devastating fungal infection commonly seen in immunocompromised individuals, including those with NHL, but it
Masaki Fujita et al.
The Japanese journal of antibiotics, 66(1), 37-43 (2013-06-20)
We report a case of pulmonary aspergillosis in lung transplant recipient who was successfully treated with inhalation administration of anti-fungal agent. The case was 33-year-old female. Two years ago, she had received lung transplant because of lymphangioleiomyomatosis. One year ago
John E Linley
Methods in molecular biology (Clifton, N.J.), 998, 149-157 (2013-03-27)
Perforated whole-cell patch-clamp is a variant of the patch-clamp technique used to measure the sum activity of ion channels in the plasma membrane of a single cell. Its defining feature is that electrical access to the cell is obtained through
Surjit Lidder et al.
Journal of the Royal Army Medical Corps, 159(2), 123-125 (2013-05-31)
Infection is the third commonest cause of total hip arthroplasty failure. Infections of the hip with Candida species are extremely rare with only a few reports in the literature. A case of a 76-year-old female subject is presented illustrating both
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