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Merck

A2411

Amphotericin B from Streptomyces sp.

solid, suitable for cell culture, BioReagent

Synonym(s):

Fungizone

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About This Item

Empirical Formula (Hill Notation):
C47H73NO17
CAS Number:
1397-89-3
Molecular Weight:
924.08
NACRES:
NA.76
PubChem Substance ID:
24890655
UNSPSC Code:
12352207
EC Number:
215-742-2
MDL number:
MFCD00877763
Beilstein/REAXYS Number:
78342

Key Documents

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Product Name

Amphotericin B from Streptomyces sp., BioReagent, suitable for cell culture, ~80% (HPLC)

InChI key

APKFDSVGJQXUKY-INPOYWNPSA-N

InChI

1S/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

SMILES string

C[C@H]1O[C@@H](O[C@@H]2C[C@@H]3O[C@](O)(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\2)C[C@H](O)[C@H]3C(O)=O)[C@@H](O)[C@@H](N)[C@@H]1O

biological source

Streptomyces sp.

product line

BioReagent

assay

~80% (HPLC)

form

solid

potency

>750.00 μg per mg (Dry basis)

technique(s)

cell culture | mammalian: suitable

color

yellow to yellow-orange

solubility

H2O: slightly soluble

antibiotic activity spectrum

fungi
yeast

mode of action

cell membrane | interferes

storage temp.

2-8°C

Quality Level

300

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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.

Biochem/physiol Actions

Amphotericin B binds to sterols, forming pores in the membrane, and causing small molecules to leak out. The product is most effective against fungi and yeast.

Disclaimer

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.

General description

Chemical structure: polyene

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Product is sensitive to light and moisture.

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.

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

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
049M4023V
108M4042V
118M4033V
068M4080V
028M4024V

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Daniel J Mullen et al.
PLoS genetics, 16(9), e1009023-e1009023 (2020-09-15)
Lung cancer is the leading cause of cancer-related death and lung adenocarcinoma is its most common subtype. Although genetic alterations have been identified as drivers in subsets of lung adenocarcinoma, they do not fully explain tumor development. Epigenetic alterations have
Malav S Trivedi et al.
The Journal of nutritional biochemistry, 25(10), 1011-1018 (2014-07-16)
Dietary interventions like gluten-free and casein-free diets have been reported to improve intestinal, autoimmune and neurological symptoms in patients with a variety of conditions; however, the underlying mechanism of benefit for such diets remains unclear. Epigenetic programming, including CpG methylation
Israel Molina et al.
The American journal of tropical medicine and hygiene, 89(1), 105-110 (2013-05-01)
Molecular methods have been proposed as an alternative tool for the diagnosis of visceral leishmaniasis (VL), but no data are available regarding use for monitoring clinical outcome. A prospective cohort study of human immunodeficiency virus-(HIV) and VL-coinfected patients was conducted
Hsin-Yun Sun et al.
Transplantation, 96(6), 573-578 (2013-07-12)
Limited data exist regarding echinocandins as antifungal prophylaxis in liver transplant recipients. The efficacy and safety of targeted prophylaxis with micafungin or amphotericin B lipid complex (ABLC) was assessed in a sequential cohort of high-risk patients (posttransplantation dialysis, retransplantation, or
Niven A Salih et al.
Tropical medicine & international health : TM & IH, 19(2), 146-152 (2014-01-18)
The aim of this study was to report the patient profile and treatment outcomes, including relapses, of patients with visceral leishmaniasis (VL) treated with liposomal amphotericin B (AmBisome) in Gedaref, Sudan. AmBisome was offered to two groups of patients: primary
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