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N3503

Sigma-Aldrich

Nystatin

≥4,400 USP units/mg

Synonym(s):

Fungicidin, Mycostatin

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About This Item

CAS Number:
1400-61-9
EC Number:
215-749-0
MDL number:
MFCD25541651
UNSPSC Code:
51101500
PubChem Substance ID:
24897647
NACRES:
NA.85

form

powder

Quality Level

200

specific activity

≥4,400 USP units/mg

solubility

water: insoluble

antibiotic activity spectrum

fungi
yeast

mode of action

cell membrane | interferes

storage temp.

−20°C

SMILES string

O[C@@H]([C@H](C)[C@H](C)O1)[C@@H](C)/C=C/C=C/CC/C=C/C=C/C=C/C=C/[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)C[C@@]3([H])[C@H](C(O)=O)[C@@H](O)C[C@](O)(O3)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)C[C@@H](O)CC1=O

InChI

1S/C47H75NO17/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)25-36(53)35(52)20-19-31(49)21-32(50)22-33(51)23-39(55)62-29(3)28(2)42(27)56/h5-6,8,10-18,27-38,40-44,46,49-54,56-58,61H,7,9,19-26,48H2,1-4H3,(H,59,60)/b6-5+,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

VQOXZBDYSJBXMA-QEKUPDCNSA-N

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General description

Nystatin is a polyene antibiotic.
Chemical structure: polyene

Application

Nystatin is used as a fungal membrane (ergosterol binding) pore forming agent and to create nystatin/ergosterol based ion channels in lipid bilayers. Its uses include preventing cell culture contamination and inducing interleukin (IL)-1, IL-8, and tumor necrosis factor α secretion in TLR2-expressing THP1 cells. This product is recommended for use in cell culture applications at 50 mg/L.

Biochem/physiol Actions

Mode of Action: Nystatin acts by binding to ergosterols in fungal cell membranes, increasing permeability of the membrane, and creating nystatin/ergosterol based ion channels. It also functions as a lipid raft-inhibiting reagent and as membrane associated cholesterol.

Antimicrobial spectrum: Nystatin acts against fungi, yeasts and molds.

Caution

Nystatin in tissue culture media is stable at 37°C for three days. It is also stable in moderately alkaline media. Solutions and aqueous suspensions begin to lose activity soon after preparation, with heat, light, and oxygen accelerating the decomposition. Aqueous suspensions are stable for 10 minutes when heating to 100°C at pH 7.

Preparation Note

Nystatin is soluble at 28°C in methanol (11.2 mg/mL), ethanol (1.2 mg/mL), carbon tetrachloride (1.23 mg/mL), chloroform (0.48 mg/mL), benzene (0.28 mg/mL), and ethylene glycol (8.75 mg/mL). It is also soluble in DMSO at 5 mg/mL and freely soluble in DMF and formamide. It is not recommended to autoclave or sterile filter solutions of Nystatin. Prepare 50 mg/mL stock suspensions in water and store at -20°C.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Store under inert gas. Air and light sensitive.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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’.

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Raymund R Razonable et al.
Antimicrobial agents and chemotherapy, 49(8), 3546-3549 (2005-07-29)
Nystatin is an antifungal compound with potent proinflammatory properties. Herein, we demonstrate that nystatin induces interleukin (IL)-1beta, IL-8, and tumor necrosis factor alpha secretion through its activation of toll-like receptor 1 (TLR1) and TLR2. Hence, a TLR-dependent mechanism could serve
Aleeza C Gerstein
Biology letters, 9(1), 20120614-20120614 (2012-10-12)
Ploidy is predicted to influence adaptation directly, yet whether single mutations behave the same in different ploidy backgrounds has not been well studied. It has often been assumed theoretically that aside from dominance, selective parameters do not differ between cells
Mariana Montenegro Silva et al.
Oral surgery, oral medicine, oral pathology and oral radiology, 114(4), 469-479 (2012-09-19)
The aim of this study was to compare the effectiveness of denture microwave disinfection and antifungal therapy on treatment of denture stomatitis. Sixty denture wearers with denture stomatitis (3 groups; n = 20 each), were treated with nystatin or denture
Santhanam Shanmughapriya et al.
Biofouling, 28(9), 929-935 (2012-09-12)
The presence of intrauterine contraceptive devices (IUDs) gives a solid surface for attachment and an ideal niche for biofilm to form and flourish. Pelvic actinomycosis is often associated with the use of IUDs. Treatment of IUD-associated pelvic actinomycosis requires the
N Akaike et al.
The Japanese journal of physiology, 44(5), 433-473 (1994-01-01)
We have reviewed the basic aspects of history, physicochemical properties, advantages, disadvantages, and applications of nystatin- and amphotericin B-perforated patch recording. Recently, we have developed a novel perforated patch technique using gramicidin [49, 132, 133]. Since gramicidin pores are permeable
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