Nystatin

Nystatin

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Nystatin
Category Antifungal
Catalog number BBF-02614
CAS 1400-61-9
Molecular Weight 926.09
Molecular Formula C47H75NO17

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BBF-02614 50 g $199 In stock

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Description

Nystatin, which belongs to the polyene group of antimycotics, is frequently used as a topical agent in the treatment of oro-pharyngeal candidosis.

Specification

Synonyms Stamycin; Nilstat; Mycostatin; Nystavescent; Biofanal
Storage Store at -20°C
IUPAC Name (1S,15S,16R,17R,18S,19E,21E,25E,27E,29E,31E)-33-[(2S,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-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
Canonical SMILES 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 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
InChI Key VQOXZBDYSJBXMA-RKEBNKJGSA-N

Properties

Appearance Yellow Solid
Antibiotic Activity Spectrum fungi
Boiling Point 476°C at 760 mmHg
Melting Point 160°C
Density 1.31 g/cm3
Solubility Soluble in DMSO
LogP 0.5

Toxicity

Carcinogenicity No indication of carcinogenicity to humans (not listed by IARC).
Mechanism Of Toxicity Nystatin interacts with 14α-demethylase, a cytochrome P-450 enzyme necessary for the conversion of lanosterol to ergosterol. This results in inhibition of ergosterol synthesis and increased fungal cellular permeability. Nystatin exerts its antifungal activity by binding to ergosterol found in fungal cell membranes. Binding to ergosterol causes the formation of pores in the membrane. Potassium and other cellular constituents leak from the pores causing cell death.

Reference Reading

1. COMBINATION OF PIPEMIDIC ACID, COLISTIN SODIUM METHANESULFONATE AND NYSTATIN MAY BE LESS EFFECTIVE THAN NYSTATIN ALONE FOR PREVENTION OF INFECTION DURING CHEMOTHERAPY-INDUCED GRANULOCYTOPENIA IN ACUTE LEUKEMIA
KAZUMI SAMPI,* MASAHARU SAKURAI. Med. Oncol. & Tumor Pharmacother. Vol. 6, No. 4,pp. 291-296, 1989
Despite intensive infection prevention programs, the clinical course of patients with granulocytopenia continues to be complicated by fever and infection. The infections are most often caused by bacteria, especially aerobic gram-negative bacilli, normally dwelling in the alimentary tract; anaerobic bacteria rarely cause infections in the immunocompromised leukemic patients. Decontamination of the alimentary tract with agents that are selectively directed against aerobic gramnegative bacilli and do not affect the anaerobic flora, therefore, may prevent infections in these patients. Several studies have shown the efficacy of trimethoprim-sulfamethoxazole, gentamicin, nalidixic acid and colistin for the prevention of infections Abbreviations used in this paper: PPA, pipemidic acid; CLM, colistin sodium methanesulfonate; NYS, nystatin; ara-C, cytarabine; HDARA-C, high dose ara-C; DNR, daunorubicin; DHAD, mitoxantrone; ACR, aclarubicin; ANLL, acute nonlymphocytic leukemia; ALL, acute lymphocytic leukemia; GVN, gentamicin, vancomycin and nystatin.
2. Nystatin prophylaxis: efficient in high-risk nonimmuno- compromised ICU patients?
Philippe Vignon, Sandrine Normand. Intensive Care Med (2006) 32:935
Adequate selection of the eligible study population is challenging since these high-risk patients are difficult to identify, and the primary end-poin of prophylaxis should be carefully determined. Since the prevalence of candidemia and severe fungal infections in ICU patients approximates 1% and 2%, respectively, a large sample size would be required to demonstrate the efficacy of antifungal prophylaxis to reduce these rates. Such trial would therefore be impractical to conduct from both economic and clinical points of view and, more importantly, would not be clinically relevant. In addition, far more patients become colonized than infected during the ICU stay, and colonization by Candida spp. Constitutes an independent risk factor for invasive candidiasis. Finally, preemptive antifungal therapy has been recently proposed in heavily colonized, nonimmunocompromised ICU patients with well established risk factors for invasive candidiasis when their general condition abruptly deteriorates. In this subset of unstable, critically ill patients, the risk of invasive candidiasis is so high that the potential benefit of immediate antifungal treatment initiated before culture results outweighs its potential side effects. Such therapeutic strategy has recently been shown to be cost-effective in a highly selected target population that may represent approx. 7% of all ICU patients. Accordingly, we believe that future trials aimed at evaluating the usefulness of nystatin prophylaxis should include the use of preemptive therapy with predefined indications as a relevant end-point in double-blind placebo-controlled studies. We hypothesize that early nystatin prophylaxis administered in nonimmunocompromised ventilated ICU patients at high risk of invasive candidiasis would reduce the progression of colonization by Candida spp.

Spectrum

Predicted LC-MS/MS Spectrum - 10V, Positive

Experimental Conditions

Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da

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