Nystatin

Nystatin
Clinical data
Trade namesMycostatin, others
AHFS/Drugs.comMonograph
MedlinePlusa682758
License data
Routes of
administration		Topical, vaginal, by mouth
Drug classPolyene antifungal medication
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability0% on oral ingestion
MetabolismNone (not extensively absorbed)
Elimination half-lifeDependent upon GI transit time
ExcretionFecal (100%)
Identifiers
  • (1S,3R,4R,7R,9R,11R,15S,16R,17R,18S,19E,21E, 25E,27E,29E,31E,33R,35S,36R,37S)-33-[(3-amino-3,6-dideoxy-β-L-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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.014.317 Edit this at Wikidata
Chemical and physical data
FormulaC47H75NO17
Molar mass926.11 g·mol−1
3D model (JSmol)
Melting point44–46 °C (111–115 °F)
  • CC1C=CC=CCCC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(C(CCC(CC(CC(CC(=O)OC(C(C1O)C)C)O)O)O)O)O)O)O)C(=O)O)OC3C(C(C(C(O3)C)O)N)O
  • InChI=1S/C47H75NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-36(53)35(52)20-19-31(49)21-32(50)22-33(51)23-39(55)62-29(3)28(2)42(27)56/h5-6,8,10-18,27-38,40-44,46,49-54,56-58,61H,7,9,19-26,48H2,1-4H3,(H,59,60)/b6-5+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33+,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1 ☒N
  • Key:VQOXZBDYSJBXMA-NQTDYLQESA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Nystatin, sold as the name Mycostatin is an antifungal medication. It is used to treat Candida (fungal) infections of the skin including diaper rash, thrush, esophageal candidiasis, and vaginal yeast infection. It may also be used to prevent yeast infection in those who are at high risk. Nystatin may be given by mouth, put in the vagina, or put on the skin.

Side effects can happen when nystatin is put on the skin. This could be burning, itching, and a rash. Side effects when nystatin is taken by mouth are vomiting and diarrhea. During pregnancy use in the vagina is safe while other forms have not been studied. It works by disrupting the cell membrane of the fungal cells.

Nystatin was discovered in 1950 by scientists Rachel Fuller Brown and Elizabeth Lee Hazen. It is listed in the World Health Organization's List of Essential Medicines. It is available as a generic medication. Nystatin is made from the bacterium Streptomyces noursei. In 2023, it was the 233rd most commonly prescribed medication in the United States, with more than 1 million prescriptions.

Medical uses

Skin, vaginal, mouth, and esophageal Candida infections usually respond well to treatment with nystatin. Infections of nails do not respond to this medication.

When nystatin is taken by mouth it is often used as a preventive treatment in people who are at risk for fungal infections. Patients with AIDS, with a CD4+ count, and people receiving chemotherapy are helped by treatment with Nystatin. It has been used in patients after liver transplantation. Another medication, fluconazole, was found to be much better. It is effective in treating oral candidiasis in elderly people who wear dentures.

Nystatin is also used in very small (less than 1500 g or 3 lb 5oz o) babies to prevent invasive fungal infections, although fluconazole is the preferred treatment. Nystatin has been found to reduce the rate of invasive fungal infections and also reduce deaths when used in these babies.

Adverse effects

Bitter taste and nausea are more common than most other effects.

When Nystatin is taken by mouth it can produce a number of effects including:

  1. Diarrhea
  2. Abdominal pain
  3. Rarely, tachycardia, bronchospasm, facial swelling, muscle aches

Both the oral nystatin used in the mouth and the kind of nystatin used on the skin can cause:

  1. Hypersensitivity reactions, including Stevens–Johnson syndrome in some cases
  2. Rash, itching, burning and acute generalized exanthematous pustulosis

Too high of a dosage can potentially lead to additional side effects such as:

  1. Nephrotoxicity
  2. Hypokalemia
  3. Chills and skin rash

How it works

When nystatin is in the right amount, it damages and forms holes in the fungal membrane. This leads to potassium (K+) leakage into the cell, acidification, and death of the fungus. Ergosterol is a sterol unique to fungi. The drug does not harm plant or animal cells. However, many of the effects of nystatin in humans are because of its binding to cholesterol. This is the effect that accounts for the nephrotoxicity observed when high serum levels of nystatin are seen. It remains unclear how the nystatin pores are formed. Researchers think that nystatin pores are formed from 4-12 nystatin molecules, with an unknown number of the necessary sterol interactions.

How it is made

Nystatin A1 (often called nystatin) is made by a bacterial strain, Streptomyces noursei. The structure of this compound is seen as a polyene macrolide with a deoxysugar D-mycosamine, an aminoglycoside. The creation of the macrolide activity follows the polyketide synthase I pathway.

The melting point of nystatin is 44 - 46°C.

History

Elizabeth Lee Hazen (left) and Rachel Fuller Brown in 1955.

Like many other antifungals and antibiotics, nystatin has bacterial origin. It was isolated from Streptomyces noursei in 1950 by Elizabeth Lee Hazen and Rachel Fuller Brown. They were doing research for the Division of Laboratories and Research of the New York State Department of Health. Hazen found a micro-organism in the soil of a friend's dairy farm. She named it Streptomyces noursei, after Jessie Nourse, the wife of the farm's owner. Hazen and Brown named nystatin after the New York State Health Department in 1954. The two discoverers patented the drug, and then donated the $13 million in profits to a foundation to fund similar research.

Other uses

Penicillium-infected tangerine: The spot absent of growth had nystatin applied to it before the fungus covered the fruit.

In certain cases, a nystatin derivative has been used to prevent the spread of mold on objects such as works of art. For example, it was applied to wood panel paintings damaged as a result of the Arno River Flood of 1966 in Florence, Italy.

Formulations

Due to its toxicity when high levels in the serum are obtained, no injectable formulations of nystatin are on the US market. However, injectable formulations have been investigated in the past.

Brand names

References

  1. 1 2 3 4 5 6 7 8 9 10 11 "Nystatin". American Society of Health-System Pharmacists. Archived from the original on 3 February 2016. Retrieved 27 January 2016.
  2. 1 2 Espinel-Ingroff AV (2013). Medical Mycology in the United States a Historical Analysis (1894-1996). Dordrecht: Springer Netherlands. p. 62. ISBN 978-94-017-0311-6. Archived from the original on 2 February 2016.
  3. ↑ The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. 2023. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  4. ↑ "The Top 300 of 2023". ClinCalc. Archived from the original on 12 August 2025. Retrieved 12 August 2025.
  5. ↑ "Nystatin Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 20 August 2025.
  6. 1 2 Hilal-Dandan R, Knollmann B, Brunton L (5 December 2017). Brunton LL, Knollmann BC, Hilal-Dandan R (eds.). Goodman & Gilman's the Pharmacological Basis of Therapeutics (Thirteenth ed.). New York: McGraw Hill / Medical. ISBN 978-1-259-58473-2. OCLC 994570810.
  7. ↑ Gøtzsche PC, Johansen HK (September 2014). "Nystatin prophylaxis and treatment in severely immunodepressed patients". The Cochrane Database of Systematic Reviews. 2014 (9) CD002033. doi:10.1002/14651858.CD002033.pub2. PMC 6457783. PMID 25188770.
  8. 1 2 Lyu X, Zhao C, Yan ZM, Hua H (2016). "Efficacy of nystatin for the treatment of oral candidiasis: a systematic review and meta-analysis". Drug Design, Development and Therapy. 10: 1161–1171. doi:10.2147/DDDT.S100795. PMC 4801147. PMID 27042008.
  9. ↑ Pappas PG, Kauffman CA, Andes D, Benjamin DK, Calandra TF, Edwards JE, et al. (March 2009). "Clinical practice guidelines for the management of candidiasis: 2009 update by the Infectious Diseases Society of America". Clinical Infectious Diseases. 48 (5): 503–535. doi:10.1086/596757. PMC 7294538. PMID 19191635.
  10. ↑ "Nystatin (Oral route)". Micromedex Detailed Drug Information. PubMed Health, U.S. National Library of Medicine. Archived from the original on 21 December 2013. Retrieved 1 April 2014.
  11. ↑ "FDA approved package insert" (PDF). Archived (PDF) from the original on 21 April 2014.
  12. ↑ Rosenberger A, Tebbe B, Treudler R, Orfanos CE (June 1998). "[Acute generalized exanthematous pustulosis, induced by nystatin]". Der Hautarzt; Zeitschrift für Dermatologie, Venerologie, und verwandte Gebiete (in German). 49 (6): 492–495. doi:10.1007/s001050050776. PMID 9675578. S2CID 10935411.
  13. 1 2 3 Groll AH, Piscitelli SC, Walsh TJ (1 January 1998), August JT, Anders MW, Murad F, Coyle JT (eds.), Clinical Pharmacology of Systemic Antifungal Agents: A Comprehensive Review of Agents in Clinical Use, Current Investigational Compounds, and Putative Targets for Antifungal Drug Development, Advances in Pharmacology, vol. 44, Academic Press, pp. 343–500, doi:10.1016/S1054-3589(08)60129-5, ISBN 978-0-12-032945-8, PMID 9547888, retrieved 9 December 2023
  14. ↑ Hammond SM (1977). Biological activity of polyene antibiotics. Progress in Medicinal Chemistry. Vol. 14. pp. 105–79. doi:10.1016/S0079-6468(08)70148-6. ISBN 978-0-7204-0645-0. PMID 345355.
  15. ↑ Helrich CS, Schmucker JA, Woodbury DJ (August 2006). "Evidence that nystatin channels form at the boundaries, not the interiors of lipid domains". Biophysical Journal. 91 (3): 1116–1127. Bibcode:2006BpJ....91.1116H. doi:10.1529/biophysj.105.076281. PMC 1563755. PMID 16679364.
  16. 1 2 Fjaervik E, Zotchev SB (June 2005). "Biosynthesis of the polyene macrolide antibiotic nystatin in Streptomyces noursei". Applied Microbiology and Biotechnology. 67 (4): 436–443. doi:10.1007/s00253-004-1802-4. PMID 15700127. S2CID 19291518.
  17. ↑ Dewick PM (2009). Medicinal Natural Products: A Biosynthetic Approach (3rd ed.). UK: John Wiley & Sons Ltd. ISBN 978-0-471-97478-9.
  18. ↑ Elsner Z, Leszczyńska-Bakal H, Pawlak E, Smazyński T (1976). "Gel with nystatin for treatment of lung mycosis". Polish Journal of Pharmacology and Pharmacy. 28 (4): 349–352. PMID 981024.
  19. ↑ Espinel-Ingroff A (2003). Medical mycology in the United States: a historical analysis (1894-1996). Springer. p. 62.
  20. ↑ Kelly K (2010). Medicine Becomes a Science: 1840-1999. Infobase. p. 71. ISBN 978-1-4381-2752-1. Archived from the original on 23 March 2017.
  21. ↑ Sicherman B, Green CH (1980). Notable American Women: The Modern Period: a Biographical Dictionary. Belknap Press of Harvard University Press. p. 327. ISBN 978-0-674-62733-8. Archived from the original on 23 March 2017.
  22. ↑ Brommelle NS (1970). "The Restoration of Damaged Art Treasures in Florence and Venice". Journal of the Royal Society of Arts. 118 (5165): 260–269. ISSN 0035-9114. JSTOR 41370578.
  23. ↑ Hamill RJ (2003). "Liposomal Nystatin". In Dismukes WE, Pappas PG, Sobel JD (eds.). Clinical Mycology. Oxford: Oxford University Press. pp. 50–53. ISBN 978-0-19-514809-1.
  24. ↑ "Nyata 100,000 Unit/Gram Topical Powder - Uses, Side Effects, and More". WebMD LLC. Retrieved 11 November 2018.