Skip to Content
Merck
All Photos(3)

Documents

A2411

Sigma-Aldrich

Amphotericin B from Streptomyces sp.

solid, suitable for cell culture, BioReagent

Sign Into View Organizational & Contract Pricing

Synonym(s):
Fungizone
Empirical Formula (Hill Notation):
C47H73NO17
CAS Number:
Molecular Weight:
924.08
Beilstein:
78342
EC Number:
MDL number:
UNSPSC Code:
12352207
PubChem Substance ID:
NACRES:
NA.76

biological source

Streptomyces sp.

Quality Level

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

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

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

InChI key

APKFDSVGJQXUKY-INPOYWNPSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

Chemical structure: polyene

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.

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.

Other Notes

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

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

STOT RE 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

Caspofungin diacetate analytical standard

Supelco

32343

Caspofungin diacetate

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
Shannon M Reilly et al.
The Journal of clinical investigation, 131(10) (2021-04-07)
The protein kinases IKKε and TBK1 are activated in liver and fat in mouse models of obesity. We have previously demonstrated that treatment with the IKKε/TBK1 inhibitor amlexanox produces weight loss and relieves insulin resistance in obese animals and patients.
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
Anna-Maria Dietl et al.
Microorganisms, 9(3) (2021-04-04)
Fungal infections due to Aspergillus species have become a major cause of morbidity and mortality among immunocompromised patients. At the Medical University of Innsbruck, A. terreus and related species are the second most common causative agents of aspergillosis. In this
Manica Balasegaram et al.
Expert opinion on emerging drugs, 17(4), 493-510 (2012-11-22)
Leishmaniasis is a parasitic disease transmitted by phlebotomine sandflies. Between 700,000 and 1.2 million cases of cutaneous leishmaniasis and between 200,000 and 400,000 cases of visceral leishmaniasis (VL), which is fatal if left untreated, occur annually worldwide. Liposomal amphotericin B

Articles

Prevent fungal, yeast, and mold contamination in cell cultures. Discover the best antifungal agent for your cultures with the extensive Sigma® antifungal collection.

Antibiotic kill curve is a dose response experiment in which mammalian cells are subjected to increasing amounts of selection antibiotic

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service