Natamycin
( 8E, 14E, 16E, 18E, 20E ) - ( 1R, 3S, 5R, 7R, 12R, 22R, 24S, 25R, 26S ) - 22 - ( 3-amino- 3 ,6 -dideoxy -25 - D- mannopyranosyloxy ) - 1,3,26 - trihydroxy -12 -methyl- 10 -oxo- 6,11,28 - trioxatricyclo [ 22.3.1.05,7 ] octacosa - 8,14,16,18,20 - pentaene -25 -carboxylic acid ( IUPAC)
- A01AB10
- A07AA03
- D01AA02
- G01AA02
- S01AA10
White to light yellow powder
Antibiotic antifungals
Fixed
280 ° C ( decomposition)
Sparingly soluble in water
2730 mg · kg -1 ( LD50, rat, oral)
Template: Infobox chemical / molecular formula search available
Natamycin is an antifungal agent produced by Streptomyces natalensis, a actinobacterium the genus Streptomyces. It is a macrolide polyene antimycotic and is used in the food industry, as a medicament. The use of natamycin as a drug is very limited.
Application in the Food Industry
Natamycin ( E 235 ) has been approved as a preservative for the surface treatment of hard cheese, sliced cheese and semi-hard cheese. Likewise, it finds use in dried and cured sausages. After the food law a maximum of 1 mg/dm2 surface applies. Natamycin shall not exceed 5 mm below the rind no longer be detectable.
In some non-EU countries, the use of natamycin is also approved for other food and beverages, such as wine. The natamycin is used on the one hand to interrupt the fermentation at a particular residual sugar content and on the other hand, as a protection against unwanted microbial contamination after fermentation by harmful organisms. In order to achieve an effect, an addition of 10 mg / L natamycin product is necessary in about.
In the EU, the use of natamycin except for the above mentioned products (cheese, sausages, etc.) is not permitted. Products imported from outside the EU, must therefore be free of natamycin.
Use as a pharmaceutical
Mechanism of action
Natamycin is an antifungal medication which is used for fungal infections ( mycoses).
It attaches itself to the ergosterol, an important component of the cell membrane of the fungi, and thus causes the formation of pores in the cell membrane. Through these pores reach potassium ions (K ), and other cell components from the fungal cell. As a result, dies from the fungal cell.
Absorption and side effects
Natamycin is not absorbed in the gut ( added ). Therefore, natamycin is used only locally. A daily dose of 300-400 mg / kg caused - given over several days - nausea, vomiting and diarrhea.
Areas of application (indications )
- Yeast infections ( candidiasis ) of the intestine
- Fungal infections of the mouth ( oral thrush )
- Fungal infections of the eye, eyelids and tear ducts
Chemical Properties
Natamycin is a white crystalline powder, which hardly dissolves in water and alcohols. Also in higher alcohols or oils it is almost insoluble. Natamycin is light sensitive and is not absorbed.