GLPBio

Natamycin

Catalog No.: GC12381Purity:>99.00%Synonyms: Antibiotic A 5283; CL 12,625; Delvocid;E 235; Mycophyt

Antifungal macrolide polyene

Products are for research use only. Not for human use. We do not sell to patients.


Natamycin
Cas No.: 7681-93-8
10mM (in 1mL DMSO)In Stock
$41.00
1
50mgIn Stock
$37.00
1
100mgIn Stock
$62.00
1
200mgIn Stock
$108.00
1
500mgIn Stock
$215.00
1

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Description

Natamycin is a naturally-occurring macrolide polyene antifungal agent produced during fermentation by the bacterium S. natalensis, commonly found in soil. With minimal inhibitory concentrations ranging from 4-64 μM, natamycin is used to treat fungal infections, including Candida, Aspergillus, Cephalosporium, Fusarium, and Penicillium.[1],[2],[3] Natamycin blocks fungal growth by binding specifically to ergosterol with an apparent affinity of ~100 μM, but it does not permeabilize cell membranes as other polyene antibiotics are known to do.[2] Natamycin is also used in the food industry as a preservative.[4]
Reference:
[1]. Lalitha, P., Vijaykumar, R., Prajna, N.V., et al. In vitro natamycin susceptibility of ocular isolates of Fusarium and Aspergillus species: Comparison of commercially formulated natamycin eye drops to pharmaceutical-grade powder. Journal of Clinical Microbiology 46(10), 3477-3478 (2008).
[2]. te Welscher, Y.M., ten Napel, H.H., Balagué, M.M., et al. Natamycin blocks fungal growth by binding specifically to ergosterol without permeabilizing the membrane. The Journal of Biological Chemisty 283(10), 6393-6401 (2008).
[3]. Dong, X.H., Gao, W.J., and He, X.P. Antifungal efficacy of natamycin in experimental fusarium solani keratitis. Int.J.Ophthalmol. 5(2), 143-146 (2012).
[4]. de Vries, R.P., de Lange, E.S., Wösten, H.A.B., et al. Control and possible applications of a novel carrot-spoilage basidiomycete, Fibulorhizoctonia psychrophila. Antonie Van Leeuwenhoek 93, 407-413 (2008).

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Protocol

Cell experiment [1]:

Cell lines

human corneal epithelial cells(HCE)

Preparation method

Soluble in DMSO > 10.75 mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.

Reacting condition

5 μM of FITC(Fluorescein isothiocyanate) labelled natamycin for 1 h at 37°C

Applications

The drug natamycin had a broad spectrum activity against filamentous fungi in the HCE, therefore, it was considered as the drug of choice for the treatment of filamentous fungi associated Keratitis.

Clinical experiment [2]:

Disease models

Patients with smear positive or culture-positive filamentous fungal corneal ulcers

Dosage form

5% natamycin plus 0.02% preservative, one drop to the affected eye every one hour while awake for 1 week, then every 2 hours while awake until 3 weeks

Application

Topical natamycin was superior to topical voriconazole for the treatment of filamentous fungal corneal ulcers, and in particular those culture-positive for Fusarium species. Vision-related functioning was higher among those treated with natamycin compared with voriconazole.

Other notes

Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.

References:

[1]. Jain A1, Shah SG, Chugh A, Cell penetrating peptides as efficient nanocarriers for delivery of antifungal compound, natamycin for the treatment of fungal keratitis. Pharm Res. 2015 Jun;32(6):1920-30. doi: 10.1007/s11095-014-1586-x. Epub 2014 Dec 3.

[2]. Rose-Nussbaumer J1,2,3, Prajna NV4, et al, Risk factors for low vision related functioning in the Mycotic Ulcer Treatment Trial: a randomised trial comparing natamycin with voriconazole. Br J Ophthalmol. 2016 Jul;100(7):929-932. doi: 10.1136/bjophthalmol-2015-306828. Epub 2015 Nov 3.

Product Documents

Purity:>99.00%Appearance:A solid

Chemical Properties

CAS No.
7681-93-8
Synonyms
Antibiotic A 5283; CL 12,625; Delvocid;E 235; Mycophyt
Chemical Name
(5R,7R,24S)-22R-[(3S-amino-3,6-dideoxy-β-D-mannopyranosyl)oxy]-1R,3S,26S-trihydroxy-12R-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8E,14E,16E,18E,20E-pentaene-25R-carboxylic acid
SMILES
O[C@](C1)(C[C@H](C[C@H]2O[C@@H]2/C=C\C(O[C@H](C)C/C=C\C=C/C=C\C=C/[C@@H]3O[C@@H]([C@H]([C@H]4N)O)O[C@H](C)[C@H]4O)=O)O)O[C@](C3)([H])[C@H](C(O)=O)[C@H]1O
Molecular Formula
C33H47NO13
Molecular Weight
665.73
Solubility
≥ 16.425mg/mL in DMSO with gentle warming
Storage
Store at -20°C
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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