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Nystatin (Fungicidin)

antifungal antibiotic CAS# 1400-61-9

Nystatin (Fungicidin)

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Chemical structure

Nystatin (Fungicidin)

3D structure

Chemical Properties of Nystatin (Fungicidin)

Cas No. 1400-61-9 SDF Download SDF
PubChem ID 6433272 Appearance Powder
Formula C47H75NO17 M.Wt 926.09
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : 50 mg/mL (53.99 mM; Need ultrasonic)
Chemical Name (4E,6E,8E,10E,14E,16E,18S,19R,20R,21S,35S)-3-[(2S,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,29,32,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,14,16-hexaene-38-carboxylic acid
SMILES CC1C=CC=CCCC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(C(CCC(CC(CC(CC(=O)OC(C(C1O)C)C)O)O)O)O)O)O)O)C(=O)O)OC3C(C(C(C(O3)C)O)N)O
Standard InChIKey VQOXZBDYSJBXMA-RKEBNKJGSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Nystatin (Fungicidin)

DescriptionNystatin is a polyene antifungal antibiotic effective against yeast and mycoplasma.In Vitro:Nystatin results in a significant reduction in buccal epithelial cell adhesion of all six Candida species[1]. Nystatin is an antibiotic that increases the permeability of plasma membranes to small monovalent ions, including chloridion. Nystatin increases apical chloridion permeability to the point where transepithelial chloridion transport is limited by transport across the basolateral membrane of tracheal epithelial cells, which reflects primarily the activity of the cotransporter. Nystatin (400 units/mL) increases the basal level of transepithelial 36Cl flux approximately 1.5-fold and eliminates UTP stimulation of this flux. Nystatin treatment also abolishes UTP stimulation of saturable, basolateral [3H]bumetanide binding, a measure of functioning Na-K-Cl cotransporters in these cells; isoproterenol stimulation of binding is only mildly inhibited by nystatin treatment[2]. Nystatin significantly enhances endostatin uptake by endothelial cells through switching endostatin internalization predominantly to the clathrin-mediated pathway. Nystatin-enhanced internalization of endostatin also increases its inhibitory effects on endothelial cell tube formation and migration[3].In Vivo:Nystatin combined with endostatin selectively enhances endostatin uptake and biodistribution in tumor blood vessels and tumor tissues but not in normal tissues of tumor-bearing mice, ultimately resulting in elevated antiangiogenic and antitumor efficacies of endostatin in vivo[3]. Liposomal Nystatin, at doses as low as 2 mg/kg of body weight/day, protects neutropenic mice against Aspergillus-induced death in a statistically significant manner at the 50-day time point compared to either the no-treatment, the saline, or the empty-liposome group[4].

References:
[1]. Ellepola AN, et al. Adhesion of oral Candida species to human buccal epithelial cells following brief exposure to nystatin. Oral Microbiol Immunol. 1999 Dec;14(6):358-63. [2]. Haas M, et al. Na-K-Cl cotransport in nystatin-treated tracheal cells: regulation by isoproterenol, apical UTP, and [Cl]i. Am J Physiol. 1994 May;266(5 Pt 1):C1440-52. [3]. Chen Y, et al. Cholesterol sequestration by nystatin enhances the uptake and activity of endostatin in endothelium via regulating distinct endocytic pathways. Blood. 2011 Jun 9;117(23):6392-403 [4]. Wallace TL, et al. Activity of liposomal nystatin against disseminated Aspergillus fumigatus infection in neutropenic mice. Antimicrob Agents Chemother. 1997 Oct;41(10):2238-43

Nystatin (Fungicidin) Dilution Calculator

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Preparing Stock Solutions of Nystatin (Fungicidin)

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.0798 mL 5.399 mL 10.7981 mL 21.5962 mL 26.9952 mL
5 mM 0.216 mL 1.0798 mL 2.1596 mL 4.3192 mL 5.399 mL
10 mM 0.108 mL 0.5399 mL 1.0798 mL 2.1596 mL 2.6995 mL
50 mM 0.0216 mL 0.108 mL 0.216 mL 0.4319 mL 0.5399 mL
100 mM 0.0108 mL 0.054 mL 0.108 mL 0.216 mL 0.27 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Nystatin (Fungicidin)

Nystatin (Fungicidin) is a polyene antifungal antibiotic [1].
Antifungal antibiotic is a pharmaceutical fungicide used to treat and prevent mycoses.
Nystatin is a polyene antifungal antibiotic that is effective against yeast and mycoplasma [1]. In liquid media, Nystatin inhibited C. albicans at concentrations of 5-20 U/ml[2].
In a 200 clinical isolates, which comprised of 113 Candida albicans, 54 Candida glabrata, 11 Candida parapsilosis, 11 Candida tropicalis and 11 Candida krusei. Nystatin exhibited MIC90 value of 4 mg/L against C. albicans isolates and all non-albicans Candida species tested. The results confirmed C. Albicans was most frequently susceptible and Nystatin could be used to treat vulvovaginal candidiasis caused by non-albicans Candida species. Nystatin would be an important choice for women affected by non-albicans Candida species which present higher resistance to the imidazole-based treatments [3].
References:
[1]. Childs AJ. Effect of Nystatin on Growth of Candida albicans During Antibiotic Therapy. Br Med J, 1956, 1(4968): 660-662.
[2]. Stewart GT. Laboratory and Clinical Studies with Nystatin in Post-antibiotic Mycotic Infections. Br Med J, 1956, 1(4968): 658-660.
[3]. Choukri F, Benderdouche M, Sednaoui P. In vitro susceptibility profile of 200 recent clinical isolates of Candida spp. to topical antifungal treatments of vulvovaginal candidiasis, the imidazoles and nystatin agents. J Mycol Med, 2014, 24(4): 303-307.

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Description

Nystatin is an orally active polyene antifungal antibiotic effective against yeast and mycoplasma. Nystatin increases the permeability of plasma membranes to small monovalent ions, including chloridion. Nystatin is a cholesterol-sequestering agent, partially prevents Oxaliplatin-induced lipid raft aggregation, DR4 and DR5 clustering, and thereby reduces apoptosis.

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