Drug/Small Molecule:
nystatin

Overview

IUPAC Name: (21E,23E,25E,27E,31E,33E)-20-[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,6,8,11,12,16,18,36-octahydroxy-35,37,38-trimethyl-2,14-dioxo-1-oxacyclooctatriaconta-21,23,25,27,31,33-hexaene-17-carboxylic acid
Trade Names: Barstatin 100; Candex; Korostatin; Myco-Triacet Ii; Mycolog-Ii; Mycostatin; Mykacet; Mykinac; Mytrex F; Nadostine; Nilstat; Nyaderm; Nysert; Nystaform; Nystatin sodium; Nystatin, sodium salt; Nystatin-Triamcinolone Acetonide; Nystex; Nystop; PMS Nystatin; Pedi-Dri; Sodium nystatin; nystatin dihydrate
Brand Mixtures: Derma-4 Ont (Neomycin Sulfate + Nystatin + Thiostrepton (Antibiotic of a Streptomyces Species) + Triamcinolone Acetonide); Flagystatin (Metronidazole + Nystatin); Kenacomb Cream (Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide); Kenacomb Mild Cream (Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide); Kenacomb Mild Ointment (Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide); Kenacomb Ointment (Gramicidin + Neomycin Sulfate + Nystatin + Triamcinolone Acetonide); Kenacomb Ont (Gramicidin + Neomycin (Neomycin Sulfate) + Nystatin + Triamcinolone Acetonide); Lidecomb Cream (Fluocinonide + Gramicidin + Neomycin Sulfate + Nystatin); Mecomb Crm 0.1% (Gramicidin + Neomycin (Neomycin Sulfate) + Nystatin + Triamcinolone Acetonide); Solvaderm Ointment (Neomycin (Neomycin Sulfate) + Nystatin + Thiostrepton (Antibiotic of a Streptomyces Species) + Triamcinolone Acetonide)
PharmGKB Accession Id: PA450666

Description

Nystatin is a polyene antifungal drug to which many molds and yeasts are sensitive, including Candida spp. Nystatin has some toxicity associated with it when given intravenously, but it is not absorbed across intact skin or mucous membranes. It is considered a relatively safe drug for treating oral or gastrointestinal fungal infections.

Indication

For treatment of cutaneous or mucocutaneous mycotic infections caused by Candida species

ATC Therapeutic Categories

  • A07AA:Antibiotics
  • D01AA:Antibiotics
  • G01AA:Antibiotics

Pharmacology and Interactions

Mechanism Of Action

Nystatin interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary for the conversion of lanosterol to ergosterol. This results in inhibition of ergosterol synthesis and increased fungal cellular permeability.

Pharmacology

Nystatin is an antibiotic which is both fungistatic and fungicidal in vitro against a wide variety of yeasts and yeast-like fungi, including Candida albicans, C. parapsilosis, C. tropicalis, C. guilliermondi, C. pseudotropicalis, C. krusei, Torulopsis glabrata, Tricophyton rubrum, T. mentagrophytes. Nystatin acts by binding to sterols in the cell membrane of susceptible species resulting in a change in membrane permeability and the subsequent leakage of intracellular components. On repeated subculturing with increasing levels of nystatin, Candida albicans does not develop resistance to nystatin. Generally, resistance to nystatin does not develop during therapy. However, other species of Candida (C. tropicalis, C. guilliermondi, C. krusei, and C. stellatoides) become quite resistant on treatment with nystatin and simultaneously become cross resistant to amphotericin as well. This resistance is lost when the antibiotic is removed. Nystatin exhibits no appreciable activity against bacteria, protozoa, or viruses.

Food Interactions

Take without regard to meals.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Absorption

Nystatin is not absorbed from intact skin or mucous membrane

Chemical Properties

Chemical Formula:

C47H75NO17

SMILES Code:

C[C@H]1/C=C/C=C/CC/C=C/C=C/C=C/C=C/[C@H](C[C@@H]([C@H]([C@@H](CC(=O)C[C@@H]([C@H](CC[C@H](C[C@H](C[C
@H](CC(=O)O[C@@H]([C@@H]([C@H]1O)C)C)O)O)O)O)O)O)C(=O)O)O)O[C@H]2[C@H]([C@H]([C@@H]([C@H](O2)C)O)N)O

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

926.0949 / 925.5035

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Metabolizing Enzymes

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00646
KEGG Compound ID:
C06572
KEGG Drug ID:
D00202
PubChem Compound ID:
11953884
PubChem Substance ID:
8801

Common Searches

Search PubMed
Search Medline Plus
Search PubChem
Search CTD

Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
The PharmGKB is financially supported by the NIH/ NIGMS and is managed at Stanford University (U01GM61374).
©2001-2010 PharmGKB.