United States Pharmacopeia (USP)
Reference Standard
Synonym: Natamycin, Pimaricin
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Empirical Formula
(Hill Notation) C33H47NO13
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Molecular
Weight 665.73
Properties
Related Categories
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grade
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USP reference standard
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InChI Key
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NCXMLFZGDNKEPB-FFPOYIOWSA-N
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Natamycin (INN), also known as pimaricin and sometimes sold as Natacyn, is a naturally
occurring antifungal agent produced
during fermentation by the bacterium Streptomyces
natalensis, commonly found in soil. Natamycin has a very low
solubility in water; however, natamycin is effective at very low levels.
Detailed description
Its minimum inhibitory concentration is less than 10 ppm for most molds. Natamycin is classified
as a macrolide polyene antifungal, and as a drug, is used to
treat fungal keratitis, an infection of the eye. It is
especially effective against Aspergillus and Fusarium corneal infections. Other common members of the polyene macrolide
antifungal family are amphotericin B, nystatin, and filipin. Natamycin is also used in the food
industry as a natural preservative.
Uses
In foods
Natamycin has been used for decades in the food
industry as a hurdle to fungal outgrowth in dairy products and other foods.
Potential advantages for the usage of natamycin might include the replacement
of traditional chemical preservatives, a neutral flavor impact, and less
dependence on pH for efficacy, as is common with chemical preservatives. It can
be applied in a variety of ways: as an aqueous suspension (such as mixed into a brine) sprayed on the product or into which the product is dipped, or
in powdered form (along with an anticaking agent such as cellulose) sprinkled on or
mixed into the product. While not currently approved for use on meats in the
United States, some countries allow natamycin to be applied to the surface of
dry and fermented sausages to prevent mold growth on the casing. Also, natamycin
is approved for various dairy applications in the United States. More
specifically, natamycin is commonly used in products such as philadelphia
cheese, cottage cheese, sour cream, yogurt, shredded cheeses, cheese slices,
and packaged salad mixes. One of the reasons for food producers to use
natamycin is to replace the artificial preservative sorbic acid.[1]
As a food additive, it has E number E235. Throughout the
European Union, it is only approved as a surface preservative for certain
cheese and dried sausage products. It must not be detectable 5 mm below
the rind. While natamycin is approved in different applications at different
levels in the world, it is approved in over 150 countries worldwide.[2]
The European Food Safety
Authority (EFSA) panel took over the responsibilities of providing
scientific food safety advice to the EU from the Scientific Committee
on Food in 2002.[3] In 2009, the EFSA
considered the proposed use levels of natamycin are safe if it is used for the
surface treatment for these cheese and sausages types.[4]
Medical
Natamycin is used to treat fungal infections,
including Candida, Aspergillus, Cephalosporium, Fusarium, and Penicillium. It is applied topically as a
cream, in eye drops, or (for oral infections) in a lozenge. Natamycin shows
negligible absorption into the body when administered in these ways. When taken
orally, little or none is absorbed from the gastrointestinal tract, making it
inappropriate for systemic infections.[5] Natamycin lozenges
are also prescribed to treat yeast infections and oral thrush. [6]
Mechanism of action
Natamcyin is able to inhibit growth of fungi by
inhibiting transport of amino acids and glucose across the plasma membrane. Natamycin performs
this function by specifically binding to ergosterol and
inhibiting membrane transport
proteins.[7]
History
Natamycin was first isolated in 1955 from fermentation
broth of a Streptomyces
natalensis cell culture. The
discovery and properties of natamycin where announced in the article,
“Pimaricin, a new antifungal antibiotic” in Antibiotics Annual in 1957. [8]
Natamycin was originally named pimaricin to honor Pietermartizburg, where Streptomyces natalensis was acquired. Pimaricin was later
renamed natamycin after the World Health
Organization (WHO) mandated that
antibiotics produced by Streptomyces end in –mycin. The name also related
to the organism producing the compound, Streptomyces
natalensis, hence the name natamycin. [8]
Safety
Natamycin does not have acute toxicity. In animal studies,
the lowest LD50 found was
2.5-4.5 mg/kg.[9] In rats, the LD50 is ≥2300 mg/kg, and doses of
500 mg/kg/day over 2 years caused no detectable differences in survival
rate, growth, or incidence of tumors. The metabolites of natamycin also
lack toxicity. The breakdown products of natamycin under various storage
conditions may have a lower LD50 than
natamycin, but in all cases, the numbers are quite high. In humans, a dose of
500 mg/kg/day repeated over multiple days caused nausea, vomiting, and
diarrhea.[10]
No evidence shows natamycin, at either
pharmacological levels or levels encountered as a food additive, can harm
normal intestinal flora, but definitive research
may not be available.[10] However, some people
are very allergic to natamycin. [11]
The EFSA has concluded that the use of natamycin as
a food additive has no relevant risk for the development of resistant fungi.[4]
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