Nystatin - ≥4,400 USP units/mg , Ergosterol sequestering agent, CAS No.1400-61-9, Ergosterol sequestering agent

CAS: 1400-61-9 Cat. No.: N141226 Formula: C₄₇H₇₅NO₁₇ Molecular Weight: 926.11 EC Number: 215-749-0

GRADE & PURITY ≥4,400 USP units/mg

Synonyms

HSDB 3138 | Caswell No. 607B | Nilstat | KS-1373 | SCHEMBL284974 | Nystex | Terrastatin | BDBM50291684 | Nystatine [INN-French] | Nystatyna [Polish] | Fengabine (USAN/INN) | AKOS016339654 | (Liposomal Nystatin)Nyotrantrade mark | Diastatin | Nystatine | D

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

A polyene antifungal antibiotic effective against yeast and mycoplasma. Induces loss of low molecular weight substances from cells with low selectivity. A cation selective ionophore that exhibits selectivity for Na+. Increases the activity of the Na+-K+ pump. Suggested concentration is 50 μg/ml.
Nystatin is a polyene, antifungal antibiotic with potent proinflammatory properties. It has many applications such as preventing cell culture contamination and inducing interleukin (IL)-, IL-8, and tumor necrosis factor α s secretion in TLR2-expressing THP1 cells . It is used as a fungal membrane (ergosterol binding) pore forming agent and to create nystatin/ergosterol based ion channels in lipid bilayers.

Specifications

Synonyms

HSDB 3138 | Caswell No. 607B | Nilstat | KS-1373 | SCHEMBL284974 | Nystex | Terrastatin | BDBM50291684 | Nystatine [INN-French] | Nystatyna [Polish] | Fengabine (USAN/INN) | AKOS016339654 | (Liposomal Nystatin)Nyotrantrade mark | Diastatin | Nystatine | D

Specifications & Purity

≥4,400 USP units/mg

Biochemical and Physiological Mechanisms

Mode of Action: Increases the permeability of the cell membrane of sensitive fungi by binding to sterols. Antimicrobial spectrum: Yeasts and molds. Nystatin binds to ergosterol in fungal cell membranes which causes the formation of pores in the membrane.

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

SEQUESTERING AGENT

Mechanism of action

Ergosterol sequestering agent

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Names and Identifiers

Pubchem Sid

528770160

Canonical 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

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

InChIKey

VQOXZBDYSJBXMA-RKEBNKJGSA-N

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

Isomeric 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

Molecular Weight

926.11

Reaxy-Rn

33487457

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=33487457&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 Aminoglycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides
• Direct Parent: Aminoglycosides
• Alternative Parents: Macrolides and analogues Hexoses O-glycosyl compounds Beta hydroxy acids and derivatives Oxanes Dicarboxylic acids and derivatives Secondary alcohols 1,2-aminoalcohols Amino acids Lactones Hemiacetals Carboxylic acid esters Polyols Oxacyclic compounds Acetals Carboxylic acids Carbonyl compounds Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Aminoglycoside core - Macrolide - Hexose monosaccharide - O-glycosyl compound - Glycosyl compound - Beta-hydroxy acid - Dicarboxylic acid or derivatives - Oxane - Hydroxy acid - Monosaccharide - 1,2-aminoalcohol - Hemiacetal - Secondary alcohol - Lactone - Carboxylic acid ester - Amino acid or derivatives - Amino acid - Carboxylic acid derivative - Polyol - Organoheterocyclic compound - Oxacycle - Acetal - Carboxylic acid - Organic nitrogen compound - Primary aliphatic amine - Organonitrogen compound - Carbonyl group - Primary amine - Hydrocarbon derivative - Organic oxide - Amine - Alcohol - Organopnictogen compound - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
• External Descriptors: nystatins

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in DMSO
• Sensitivity: Light sensitive；Moisture sensitive
• Melt Point(°C): 160°C
• Molecular Weight: 926.100 g/mol
• XLogP3: -0.200
• Hydrogen Bond Donor Count: 12
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 3
• Exact Mass: 925.503 Da
• Monoisotopic Mass: 925.503 Da
• Topological Polar Surface Area: 320.000 Ų
• Heavy Atom Count: 65
• Formal Charge: 0
• Complexity: 1620.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• Undefined Atom Stereocenter Count: 9
• Defined Bond Stereocenter Count: 6
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 6
• Covalently-Bonded Unit Count: 1