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

pka

pKa 5.72(MeOH/2-methoxyethanol/ H2O) (Uncertain);8.64 (Uncertain)

color 

yellow

Odor

ofcereals odor

Water Solubility 

0.36g/L(24 ºC)

Merck 

13,6770

BCS Class

3

InChIKey

VXWFKTGGEJLHPP-OQMKPJEFSA-N

CAS DataBase Reference

1400-61-9

EPA Substance Registry System

Nystatin (1400-61-9)

Safety Information

Hazard Codes 

F,C

Risk Statements 

11-34

Safety Statements 

22-24/25-45-36/37/39-26-16

WGK Germany 

3

RTECS 

RF5950000

F 

10-8-23

HazardClass 

3

HS Code 

38210000

Hazardous Substances Data

1400-61-9(Hazardous Substances Data)

Toxicity

LD50 i.p. in mice: ~200 mg/kg (Seneca)

MSDS

• Language:English Provider:SigmaAldrich

Nystatin Usage And Synthesis

Description

Nystatin was found in the mycelium of Streptomyces noursei in 1950 and produced on an industrial scale by Squibb & Sons Co. in 1954. This antibiotic was used orally and topically as the first clinically applied polyene macrolide with antifungal properties. Nystatin shows activity against Candida and filamentous fungi and is used to treat Candida infections of the mouth, digestive organs, and vagina. The application of nystatin in combination with gentamicin and vancomycin to sterilize the gut in perioperation of bone-marrow transplantation has been developed recently.

Chemical Properties

This substance is a yellow or yellow-brown powder with a unique smell and the ability to absorb moisture. It dissolves to a small extent in water, methanol, and ethanol, but cannot dissolve in acetone, ether, or chloroform. It is not stable when exposed to air, light, heat, water, acid, or alkali.

Originator

Mycostatin,Squibb,US,1954

Uses

Polyene 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.

Uses

Nystatin 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.

Definition

ChEBI: A polyene macrolide antibiotic; part of the nystatin complex produced by several Streptococcus species. The keto-form of nystatin A1.

Indications

Nystatin (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 Process

A typical isolation and recovery procedure for nystatin is described in US Patent 2,797,183 and is shown in the following diagram:

brand name

Barstatin 100 (Barlan); Candex (Bayer); Korostatin (Holland Rantos); Mycostatin (Bristol-Myers Squibb); Mycostatin (Westwood-Squibb).

Therapeutic Function

Antifungal

General Description

Nystatin (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.

Biochem/physiol Actions

Potency: ≥3000 units/mg (anhydrous).

Pharmacology

Nystatin 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 Use

Nystatin, 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 Profile

Poison 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 Treatments

Orally 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.

Metabolism

No significant gastrointestinal absorption.

Purification Methods

Nystatin 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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