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Merck
CN

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

Key Documents

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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.

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

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.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H372

Precautionary Statements

P260 - P264 - P270 - P314 - P501

Hazard Classifications

STOT RE 1

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品
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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
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
Anil Bhansali et al.
The Journal of the Association of Physicians of India, 60, 54-58 (2013-06-20)
Histoplasmosis has been sporadically reported from India. Though asymptomatic adrenal involvement has been described in patients with disseminated histoplasmosis; isolated adrenal involvement with adrenal insufficiency (AI) as the presenting manifestation of the disease is rare. We describe 5 immunocompetent men
Gurpreet Singh et al.
Journal of pediatric hematology/oncology, 35(3), e127-e129 (2013-03-21)
Hemophagocytic lymphohistiocytosis (HLH) associated with visceral leishmaniasis (VL) is a very rare phenomenon. We report the first known North American case in a 21 month old boy. He was initially diagnosed with Epstein Barr virus (EBV) triggered HLH and treated
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
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