Nystatin

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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[1][2]. Nystatin is a cholesterol-sequestering agent[3], partially prevents Oxaliplatin-induced lipid raft aggregation, DR4 and DR5 clustering, and thereby reduces apoptosis[5].

CAS Number

1400-61-9

UNSPSC

12352005

Hazard Statement

H302, H312, H332

Target

Antibiotic; Apoptosis; Bacterial; Fungal

Type

Natural Products

Related Pathways

Anti-infection; Apoptosis

Applications

COVID-19-immunoregulation

Field of Research

Infection; Cancer

Assay Protocol

https://www.medchemexpress.com/Nystatin.html

Purity

95.68

Solubility

DMSO : 50 mg/mL (ultrasonic)

Smiles

C[C@@H]1OC(C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@@](O)(O[C@H]2C[C@H](/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@@H]([C@@H](O)[C@H]1C)C)O[C@H]3[C@@H](O)[C@@H](N)[C@H](O)[C@@H](C)O3)C[C@H](O)[C@H]2C(O)=O)=O

Molecular Formula

C47H75NO17

Molecular Weight

926.09

Precautions

H302, H312, H332

References & Citations

[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|[5]Xu L, et al. Oxaliplatin enhances TRAIL-induced apoptosis in gastric cancer cells by CBL-regulated death receptor redistribution in lipid rafts.FEBS Lett. 2009 Mar 4;583 (5) :943-8.

Shipping Conditions

Blue Ice

Storage Conditions

-20°C (Powder, sealed storage, away from moisture and light)

Scientific Category

Natural Products

Clinical Information

Launched

Chemical Information

Nystatin [USP:INN:BAN:JAN]

Nystatin is a polyene antifungal drug that has broad-spectrum fungicidal and fungistatic activity against a number of yeasts and fungi, most notably Candida species. It is one of the most effective antifungal agents synthesized by bacteria, in this case a strain of Streptomyces noursei, and is closely related to [amphotericin B], differing only slightly in structure. Nystatin has a greater antifungal activity than amphotericin B - parenterally administered nystatin, however, is associated with significant toxicity and is not available in a formulation appropriate for systemic use. As it undergoes very little absorption following oral or topical administration, nystatin's efficacy is limited to the treatment/prevention of cutaneous, mucocutaneous, and gastrointestinal fungal infections.

CAS Number	1400-61-9
PubChem CID	6433272
IUPAC Name	(1S,15S,16R,17R,18S,19E,21E,25E,27E,29E,31E)-33-[(2S,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylic acid
Molecular Formula	C47H75NO17
Molecular Weight	926.1
XLogP	-0.2
Topological Polar Surface Area	320
Hydrogen Bond Donor Count	12
Hydrogen Bond Acceptor Count	18
Rotatable Bond Count	3
Heavy Atom Count	65
Formal Charge	0
Complexity	1620

SMILES

C[C@H]1/C=C/C=C/CC/C=C/C=C/C=C/C=C/C(CC2C(C(C[C@](O2)(CC(C(CCC(CC(CC(CC(=O)O[C@H]([C@@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O[C@@H]3[C@H]([C@H]([C@@H]([C@H](O3)C)O)N)O

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

InChIKey

VQOXZBDYSJBXMA-RKEBNKJGSA-N

Chemical Structure

2D Structure

CAS: 1400-61-9

CID: 6433272

Formula: C47H75NO17

MW: 926.1

Interactive 3D Structure

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Computed Properties

Property	Value
Molecular Weight	926.1
XLogP3	-0.2
Hydrogen Bond Donor Count	12
Hydrogen Bond Acceptor Count	18
Rotatable Bond Count	3
Exact Mass	925.50349992
Monoisotopic Mass	925.50349992
Topological Polar Surface Area	320 Å²
Heavy Atom Count	65
Formal Charge	0
Complexity	1620
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	9
Defined Bond Stereocenter Count	6
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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