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Nystatin Basic information
Nystatin Chemical Properties
  • Melting point:>155°C (dec.)
  • alpha D25 -10° (glacial acetic acid); +21° (pyridine); +12° (DMF); -7° (0.1N HCl in methanol)
  • storage temp. -20°C
  • solubility H2O: insoluble
  • form suspension
  • pkapKa 5.72(MeOH/2-methoxyethanol/ H2O) (Uncertain);8.64 (Uncertain)
  • color yellow
  • Odorsuggestive ofcereals odor
  • Water Solubility 0.36g/L(24 ºC)
  • Merck 13,6770
  • CAS DataBase Reference1400-61-9
  • EPA Substance Registry SystemNystatin (1400-61-9)
Safety Information
Nystatin Usage And Synthesis
  • Chemical PropertiesBrown Solid
  • OriginatorMycostatin,Squibb,US,1954
  • UsesAntifungal;Performs membrane ionophores
  • UsesNystatin is polyene antifungal containing a conjugated tetraene and a diene, isolated as a complex of three components A1, A2 and A3 from Streptomyces noursei and first reported in 1950. Nystatin, like most polyene antifungals, binds to sterols in the fungal cell membrane leading to formation of ion channels in the wall, ion imbalance and cell death. Nystatin is an established bioprobe and widely-used antifungal reagent with over 4,000 literature citations.
  • UsesPolyene antifungal antibiotic complex containing 3 biologically active components, A1, A2, A3. Increases the permeability of the cell membrane of sensitive fungi by binding to sterols. Cell culture tested. Growth promotant. Nystatin A1 is shown.
  • DefinitionChEBI: A polyene macrolide antibiotic; part of the nystatin complex produced by several Streptococcus species. The keto-form of nystatin A1.
  • IndicationsNystatin (Mycostatin) is a polyene antifungal drug with a ring structure similar to that of amphotericin B and a mechanism of action identical to that of amphotericin B. Too toxic for systemic use, nystatin is limited to the topical treatment of superficial infections caused by C. albicans. Infections commonly treated by this drug include oral candidiasis (thrush), mild esophageal candidiasis, and vaginitis.
  • Manufacturing ProcessA typical isolation and recovery procedure for nystatin is described in US Patent 2,797,183 and is shown in the following diagram:
  • brand nameBarstatin 100 (Barlan); Candex (Bayer); Korostatin (Holland Rantos); Mycostatin (Bristol-Myers Squibb); Mycostatin (Westwood-Squibb).
  • Therapeutic Function Antifungal
  • General DescriptionNystatin (Mycostatin) is a polyene antibiotic that was first isolated in 1951 from a strain of the actinomycete Streptomyces noursei by Hazen and Brown.33 It occurs as a yellow to light tan powder. Nystatin is very slightly soluble in water and sparingly soluble in organic solvents. The compound is unstable to moisture, heat, and light. The aglycone portion of nystatin is called nystatinolide. The complete structure of nystatin has been determined by chemical degradation and x-ray crystallography.35 Nystatin is not absorbed systemically when administered by the oral route. It is nearly insoluble under all conditions. It is also too toxic to be administered parenterally. Hence, it is used only as a topical agent. Nystatin is a valuable agent for the treatment of local and gastrointestinal monilial infections caused by C. albicans and other Candida species. For the treatment of cutaneous and mucocutaneous candidiasis, it is supplied as a cream, an ointment, and a powder. Vaginal tablets are available for the control of vaginal candidiasis. Oral tablets and troches are used in the treatment of gastrointestinal and oral candidiasis. Combinations of nystatin with tetracycline can be used to prevent monilial overgrowth caused by the destruction of bacterial microflora of the intestine during tetracycline therapy.
  • PharmacologyNystatin is stereoisomeric 33-[(3-amino-3,6-dideoxy-β-D-mannopyranosyl) 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-hexaen-36-carboxylic acid (35.1.2). Nystatin was isolated in 1949 from the products of the vital activity of the actinomycete Streptomyces noursei, and it was the first antifungal antibiotic to be discovered. This polyene antibiotic is structurally similar to amphotericin B. It has a broad spectrum of activity. The mechanism of antifungal activity is similar to the mechanism of action of amphotericin B. It is used for preventing and treating candida infections of the skin and mucous membranes. In terms of preventative action, it is used for preventing the development of candidomycosis during prolonged treatment with penicillin drugs and antibiotics of other group, especially during oral use of tetracycline antibiotics, levomecytin, and others. Synonyms of this drug are biofanal, moronal, nicporil, fazigin, candex, and others.
  • Clinical UseNystatin, the first clinically useful polyene antifungal antibiotic, is a conjugated tetraene isolated from cultures of the bacterium Streptomyces noursei in 1951. Nystatin is an effective topical antifungal against a wide variety of organisms and is available in a variety of creams and ointments. Nystatin is too toxic to be used systemically, but because very little drug is absorbed following oral administration, it may be administered by mouth to treat fungal infections of the mouth and gastrointestinal tract.
  • Safety ProfilePoison by intraperitoneal and intravenous routes. Moderately toxic by subcutaneous route. Mildly toxic by ingestion. An experimental teratogen. Mutation data reported. An antibiotic. When heated to decomposition it emits toxic fumes of NOx.
  • Veterinary Drugs and TreatmentsOrally administered nystatin is used primarily for the treatment of oral or gastrointestinal tract Candida infections in dogs, cats, and birds; it has been used less commonly in other species for the same indications.
  • Purification MethodsNystatin is a light yellow powder with the following solubilities at ~28o: MeOH (1.1%), ethylene glycol (0.9%), H2O (0.4%), CCl4 (0.12%), EtOH (0.12%), CHCl3 (0.05%) and *C6H6 (0.03%). It has been precipitated from MeOH solution by addition of H2O. Aqueous suspensions of this macrolide antifungal antibiotic are stable at 100o/10minutes at pH 7.0 but decompose rapidly at pH <2 and >9, and in the presence of light and O2. [Birch et al. Tetrahedron Lett 1491, 1485 1964, Weiss et al. Antibiot Chemother 7 374 1957.] It may contain a mixture of components A1, A2 and A3. [Beilstein 18 III/IV 7480.]
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