Nystatin
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MedKoo CAT#: 326754

CAS#: 1400-61-9

Description: Nystatin is a polyene antifungal, the antibiotic complex containing three biologically active components: A1, A2, and A3. Nystatin is used to treat fungal infections of the skin, mouth, vagina, and intestinal tract. Fungal medicines will not work for colds, flu, or other viral infections. Nystatin binds to ergosterol, a major component of the fungal cell membrane. When present in sufficient concentrations, it forms pores in the membrane that lead to K+ leakage, acidification, and death of the fungus. Ergosterol is unique to fungi, so the drug does not have such catastrophic effects on animals or plants. However, many of the systemic/toxic effects of nystatin are attributable to its effect on human cells via binding to mammalian sterols, namely cholesterol. This is the effect that accounts for the nephrotoxicity observed when high serum levels of nystatin are achieved.


Chemical Structure

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Nystatin
CAS# 1400-61-9

Theoretical Analysis

MedKoo Cat#: 326754
Name: Nystatin
CAS#: 1400-61-9
Chemical Formula: C47H75NO17
Exact Mass: 925.50
Molecular Weight: 926.110
Elemental Analysis: C, 60.96; H, 8.16; N, 1.51; O, 29.37

Price and Availability

Size Price Availability Quantity
1g USD 150 Ready to ship
2g USD 250 Ready to ship
5g USD 450 Ready to ship
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Synonym: Nystatin; Mycostatin. AI3-26526; Barstatin 100; Biofanal; Candex; Candex Lotion; Candio-hermal; Diastatin; Fungicidin; Herniocid; HSDB 3138; Korostatin; Moronal; Myconystatin; Mycostatin; Nilstat; Nistatin; Nistatina; NSC 150817; Nyamyc; Nyotran; Nysert; Nystan; Nystatin; Nystatine; Nystavescent; Nystex; Nystop; O-V Statin; Stamycin; Zydin E

IUPAC/Chemical Name: (1S,3S,4R,7R,9R,11S,15S,16R,17R,18S,19E,21E,25Z,27E,29E,31E,33S,35S,36S,37S)-33-(((2S,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)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

InChi Key: VQOXZBDYSJBXMA-JKMCSYCMSA-N

InChi Code: 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

SMILES Code: O=C(O)[C@@H]1[C@H]2O[C@](O)(C[C@H](O)[C@H](O)CC[C@H](C[C@H](C[C@H](O)CC(O[C@H]([C@H](C)[C@@H]([C@H](/C=C/C=C/CC/C=C\C=C\C=C\C=C\[C@H](C2)O[C@@H]3[C@@H](O)[C@@H](N)[C@H](O)[C@@H](C)O3)C)O)C)=O)O)O)C[C@@H]1O

Appearance: Solid powder

Purity: Potency: 4400 units/mg min. (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Safety Data Sheet (SDS):
Biological target: Nystatin is a polyene antifungal antibiotic effective against yeast and mycoplasma.
In vitro activity: We investigated the in vitro activity of nystatin and liposomal nystatin against 103 Candida isolates to determine the effect of both time and medium on MICs. We also compared the nystatin MICs with those of amphotericin B and fluconazole. Nystatin MICs in RPMI-2 were in general similar to or slightly higher than those in RPMI at both 24 and 48 h. Nystatin MIC ranges in RPMI and RPMI-2 were similarly wide for all species other than C. glabrata. AM3 consistently generated the highest nystatin MICs at both 24 and 48 h. This effect resulted in a wide nystatin MIC range in AM3, with a shift toward higher MICs. Amphotericin B MICs for five isolates in the group of randomly selected clinical isolates were also found to be ≥0.25 μg/ml. This made a total of nine isolates which were putatively amphotericin B resistant. Relatively higher nystatin and liposomal nystatin MICs were associated with increased amphotericin B MICs. However, MICs of nystatin for the isolates that were putatively resistant to amphotericin B (MIC, ≥ 0.25 μg/ml) (2, 28) were not always elevated (Table3). While nystatin and liposomal nystatin MICs for two (Y537 and MY1012) and three (CL2887, Y537, and MY1012) of the nine amphotericin B-resistant isolates, respectively, were high (4 to >16 μg/ml), the remaining seven and six isolates, respectively, yielded nystatin and liposomal nystatin MICs that were lower than the MIC90 for the overall population of the corresponding drug. J Clin Microbiol. 2002 Apr; 40(4): 1406–1412. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC140327/
In vivo activity: The purpose of this study was to examine the activity of liposomal nystatin against a disseminated Aspergillus fumigatus infection in neutropenic mice. Mice were made neutropenic with 5-fluorouracil and were administered the antifungal drug intravenously for 5 consecutive days beginning 24 h following infection. Liposomal nystatin, at doses as low as 2 mg/kg of body weight/day, protected neutropenic mice against Aspergillus-induced death in a statistically significant manner at the 50-day time point compared to either the no-treatment, the saline, or the empty-liposome group. This protection was approximately the same as that for free nystatin, a positive control. Histopathological results showed that liposomal nystatin cleared the lungs, spleen, pancreas, kidney, and liver of Aspergillus and that there was no organ damage at the day 5 time point, which was after only three doses of liposomal nystatin. Based on these results in mice, it is probable that liposomal nystatin will be effective against Aspergillus infection in humans. Antimicrob Agents Chemother. 1997 Oct;41(10):2238-43. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC164099/pdf/412238.pdf

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.0 54.00

Preparing Stock Solutions

The following data is based on the product molecular weight 926.11 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Najafi S, Sheykhbahaei N, Khayamzadeh M, Gholizadeh N. The effect of low level laser on number of Candida albicans colonies in-vitro: a new finding. BMC Oral Health. 2019 Jun 13;19(1):104. doi: 10.1186/s12903-019-0814-5. PMID: 31196043; PMCID: PMC6567648. 2. Najafi S, Sheykhbahaei N, Khayamzadeh M, Gholizadeh N. The effect of low level laser on number of Candida albicans colonies in-vitro: a new finding. BMC Oral Health. 2019 Jun 13;19(1):104. doi: 10.1186/s12903-019-0814-5. PMID: 31196043; PMCID: PMC6567648. 3. Wallace TL, Paetznick V, Cossum PA, Lopez-Berestein G, Rex JH, Anaissie E. Activity of liposomal nystatin against disseminated Aspergillus fumigatus infection in neutropenic mice. Antimicrob Agents Chemother. 1997 Oct;41(10):2238-43. doi: 10.1128/AAC.41.10.2238. PMID: 9333054; PMCID: PMC164099. 4. Song R, Yan F, Cheng M, Dong F, Lin Y, Wang Y, Song B. Ultrasound-Assisted Preparation of Exopolysaccharide/Nystatin Nanoemulsion for Treatment of Vulvovaginal Candidiasis. Int J Nanomedicine. 2020 Mar 25;15:2027-2044. doi: 10.2147/IJN.S241134. PMID: 32273700; PMCID: PMC7104221.
In vitro protocol: 1. Najafi S, Sheykhbahaei N, Khayamzadeh M, Gholizadeh N. The effect of low level laser on number of Candida albicans colonies in-vitro: a new finding. BMC Oral Health. 2019 Jun 13;19(1):104. doi: 10.1186/s12903-019-0814-5. PMID: 31196043; PMCID: PMC6567648. 2. Najafi S, Sheykhbahaei N, Khayamzadeh M, Gholizadeh N. The effect of low level laser on number of Candida albicans colonies in-vitro: a new finding. BMC Oral Health. 2019 Jun 13;19(1):104. doi: 10.1186/s12903-019-0814-5. PMID: 31196043; PMCID: PMC6567648.
In vivo protocol: 1. Wallace TL, Paetznick V, Cossum PA, Lopez-Berestein G, Rex JH, Anaissie E. Activity of liposomal nystatin against disseminated Aspergillus fumigatus infection in neutropenic mice. Antimicrob Agents Chemother. 1997 Oct;41(10):2238-43. doi: 10.1128/AAC.41.10.2238. PMID: 9333054; PMCID: PMC164099. 4. Song R, Yan F, Cheng M, Dong F, Lin Y, Wang Y, Song B. Ultrasound-Assisted Preparation of Exopolysaccharide/Nystatin Nanoemulsion for Treatment of Vulvovaginal Candidiasis. Int J Nanomedicine. 2020 Mar 25;15:2027-2044. doi: 10.2147/IJN.S241134. PMID: 32273700; PMCID: PMC7104221.

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1: Gøtzsche PC, Johansen HK. Nystatin prophylaxis and treatment in severely immunodepressed patients. Cochrane Database Syst Rev. 2014 Sep 4;(9):CD002033. doi: 10.1002/14651858.CD002033.pub2. Review. PubMed PMID: 25188770.

2: Blyth CC, Barzi F, Hale K, Isaacs D. Chemoprophylaxis of neonatal fungal infections in very low birthweight infants: efficacy and safety of fluconazole and nystatin. J Paediatr Child Health. 2012 Sep;48(9):846-51. doi: 10.1111/j.1440-1754.2012.02543.x. Review. PubMed PMID: 22970680.

3: Isaacs D. Fungal prophylaxis in very low birth weight neonates: nystatin, fluconazole or nothing? Curr Opin Infect Dis. 2008 Jun;21(3):246-50. doi: 10.1097/QCO.0b013e3282f8adab. Review. PubMed PMID: 18448968.

4: Lye WC. Nystatin prophylaxis for fungal peritonitis: to be or not to be? Perit Dial Int. 2007 Sep-Oct;27(5):511-3. Review. PubMed PMID: 17704437.

5: Fjaervik E, Zotchev SB. Biosynthesis of the polyene macrolide antibiotic nystatin in Streptomyces noursei. Appl Microbiol Biotechnol. 2005 Jun;67(4):436-43. Epub 2005 Feb 8. Review. PubMed PMID: 15700127.

6: Gøtzsche PC, Johansen HK. Nystatin prophylaxis and treatment in severely immunodepressed patients. Cochrane Database Syst Rev. 2002;(4):CD002033. Review. Update in: Cochrane Database Syst Rev. 2014;9:CD002033. PubMed PMID: 12519566.

7: Gøtzsche PC, Johansen HK. Nystatin prophylaxis and treatment in severely immunodepressed patients. Cochrane Database Syst Rev. 2002;(2):CD002033. Review. Update in: Cochrane Database Syst Rev. 2002;(4):CD002033. PubMed PMID: 12076436.

8: Arikan S, Rex JH. Nystatin LF (Aronex/Abbott). Curr Opin Investig Drugs. 2001 Apr;2(4):488-95. Review. PubMed PMID: 11566004.

9: Gotzsche PC, Johansen HK. Nystatin prophylaxis and treatment in severely immunodepressed patients. Cochrane Database Syst Rev. 2000;(2):CD002033. Review. Update in: Cochrane Database Syst Rev. 2002;(2):CD002033. PubMed PMID: 10796846.

10: Alvarez Alvarez ME, Sánchez-Sousa A, Baquero F. A reevaluation of nystatin in prophylaxis and treatment of oropharyngeal candidiasis. Rev Esp Quimioter. 1998 Dec;11(4):295-315. Review. PubMed PMID: 9990144.

11: Rosenberger A, Tebbe B, Treudler R, Orfanos CE. [Acute generalized exanthematous pustulosis, induced by nystatin]. Hautarzt. 1998 Jun;49(6):492-5. Review. German. PubMed PMID: 9675578.

12: Schäfer-Korting M, Blechschmidt J, Korting HC. Clinical use of oral nystatin in the prevention of systemic candidosis in patients at particular risk. Mycoses. 1996 Sep-Oct;39(9-10):329-39. Review. PubMed PMID: 9009654.

13: Taylor TL. Nystatin prophylaxis in immunocompromised children. Ann Pharmacother. 1996 May;30(5):534-5. Review. PubMed PMID: 8740337.

14: Palková Z, Vondrejs V. Nystatin-rhodamine B assay for estimating activity of killer toxin from Kluyveromyces lactis. Methods Mol Biol. 1996;53:325-9. Review. PubMed PMID: 8924993.

15: Akaike N, Harata N. Nystatin perforated patch recording and its applications to analyses of intracellular mechanisms. Jpn J Physiol. 1994;44(5):433-73. Review. PubMed PMID: 7534361.

16: Finkelstein A, Holz R. Aqueous pores created in thin lipid membranes by the polyene antibiotics nystatin and amphotericin B. Membranes. 1973;2:377-408. Review. PubMed PMID: 4585230.

17: Witten VH, Katz SI. Nystatin. Med Clin North Am. 1970 Sep;54(5):1329-37. Review. PubMed PMID: 4919155.

18: Gemeinhardt H. [What is nystatin?]. Z Arztl Fortbild (Jena). 1966 Apr 15;60(8):503-6. Review. German. PubMed PMID: 4862458.