Nystatin
[CAS# 1400-61-9]

Identification

• Classification: API >> Antibiotics >> Polyene
• Name: Nystatin
• Synonyms: 33-[(3-Amino-3,6-dideoxy-beta-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-hexaene-36-carboxylic acid; Fungicidin; Mycostatin
• Molecular Formula: C₄₇H₇₅NO₁₇
• Molecular Weight: 926.10
• CAS Registry Number: 1400-61-9
• EC Number: 215-749-0
• 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

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.607, Calc.^*
• Boiling Point: 1132.2±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 638.5±34.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	1	H300

Discovery and Applications

Nystatin, an antifungal medication, was discovered in the 1950s by researchers at the New York State Department of Health and the pharmaceutical company Squibb. Its discovery stemmed from the screening of soil samples for substances with antifungal properties. Nystatin was isolated from a strain of Streptomyces noursei, a species of actinobacteria found in soil. This groundbreaking discovery marked the beginning of a new era in the treatment of fungal infections, particularly those caused by Candida species.

Nystatin is primarily used in the treatment of candidiasis, a fungal infection caused by Candida species. It is particularly effective against Candida albicans, a common pathogen responsible for oral thrush, vaginal yeast infections, and cutaneous candidiasis. Nystatin works by binding to ergosterol, a key component of fungal cell membranes, disrupting membrane integrity and leading to cell death. Its fungicidal activity makes it an essential medication in the management of candidiasis. Nystatin oral suspension is often prescribed for the treatment of oral thrush in infants. This common fungal infection occurs in the mouth and throat, causing white patches on the tongue, inner cheeks, and roof of the mouth. Nystatin vaginal cream or suppositories are used for the treatment of vaginal yeast infections, also known as vulvovaginal candidiasis. Nystatin exerts its antifungal effects locally, effectively eliminating yeast overgrowth and restoring the natural balance of vaginal flora. Nystatin is sometimes prescribed prophylactically to prevent fungal infections in immunocompromised patients, such as those undergoing chemotherapy or organ transplantation. By suppressing the growth of Candida species, nystatin helps reduce the risk of invasive fungal infections in vulnerable patient populations. Nystatin cream or ointment is used for the topical treatment of cutaneous candidiasis, a fungal infection of the skin and mucous membranes. It is applied directly to affected areas, such as the groin, armpits, or between skin folds, where Candida overgrowth is common. Nystatin cream effectively relieves itching, redness, and inflammation associated with cutaneous candidiasis.

References

1971. [Effect of nystatin and levorin on the biosynthesis of sterols and fatty acids in cell-free extracts of Saccharomyces cerevisiae]. Antibiotiki, 16(3).
URL: https://pubmed.ncbi.nlm.nih.gov/4997644

1979. A COMPARISON BETWEEN THE EFFECTS OF NYSTATIN, CLOTRIMAZOLE AND MICONAZOLE ON VAGINAL CANDIDIASIS. BJOG: An International Journal of Obstetrics & Gynaecology, 86(7).
DOI: 10.1111/j.1471-0528.1979.tb10812.x

1990. Changes in membrane lipids and amino acid transport in a nystatin-resistant Aspergillus niger. Canadian Journal of Microbiology, 36(6).
DOI: 10.1139/m90-076