1400-61-9 Usage
Description
Nystatin, also known as Mycostatin, is a polyene antibiotic that was first isolated in 1951 from a strain of the actinomycete Streptomyces noursei. It occurs as a yellow to light tan powder and is very slightly soluble in water and sparingly soluble in organic solvents. Nystatin 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. It is a valuable agent for the treatment of local and gastrointestinal monilial infections caused by C. albicans and other Candida species.
Uses
1. Used in Antifungal Applications:
Nystatin is used as an antifungal agent for treating local and gastrointestinal monilial infections caused by Candida species. It functions as a membrane ionophore, binding to sterols in the fungal cell membrane, leading to the formation of ion channels in the wall, ion imbalance, and cell death.
2. Used in Pharmaceutical Industry:
Nystatin is used as a bioprobe and a widely-used antifungal reagent in the pharmaceutical industry. It is an established compound with over 4,000 literature citations.
3. Used in Cell Culture Testing:
Nystatin is used in cell culture testing to increase the permeability of the cell membrane of sensitive fungi by binding to sterols, which helps in studying the effects on fungal growth and development.
4. Used as a Growth Promotant:
Nystatin is used as a growth promotant in certain applications, possibly due to its antifungal properties that can help prevent fungal infections and promote healthy growth in certain organisms.
5. Used in Topical Treatments:
Nystatin is used as a topical agent for the treatment of cutaneous and mucocutaneous candidiasis. It is supplied in various forms such as cream, ointment, and powder.
6. Used in Vaginal Tablets:
Nystatin is used in vaginal tablets for the control of vaginal candidiasis.
7. Used in Oral Treatments:
Oral tablets and troches containing nystatin are used in the treatment of gastrointestinal and oral candidiasis.
8. Used in Combination Therapy:
Nystatin can be combined with tetracycline to prevent monilial overgrowth caused by the destruction of bacterial microflora of the intestine during tetracycline therapy.
Brand Names:
Some brand names for Nystatin include Barstatin 100 (Barlan), Candex (Bayer), Korostatin (Holland Rantos), Mycostatin (Bristol-Myers Squibb), and Mycostatin (Westwood-Squibb).
Originator
Mycostatin,Squibb,US,1954
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:
Therapeutic Function
Antifungal
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.
Drug interactions
Potentially hazardous interactions with other drugs
None known
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 1400-61-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,0 and 0 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1400-61:
(6*1)+(5*4)+(4*0)+(3*0)+(2*6)+(1*1)=39
39 % 10 = 9
So 1400-61-9 is a valid CAS Registry Number.
InChI:InChI=1/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-10H,2,11-17H2,1H3,(H,19,20)
