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CAS NUMBER: 7681-93-8
EC NUMBER: 231-683-5
MOLECULAR FORMULA: C33H47NO13
MOLECULAR WEIGHT: 665.73
Natamycin is a polyene amphoteric macrolide antibiotic with antifungal properties.
Natamycin exerts its antifungal effects by binding to sterols in the fungal cell membrane thereby increasing membrane permeability.
This leads to a leakage and loss of essential cellular constituents.
Following ocular application, natamycin is retained in the conjunctival fornices and attains effective concentrations within the corneal stroma where it exerts its effect.
Natamycin, also known as Natamycin, is an antifungal medication used to treat fungal infections around the eye.
This includes infections of the eyelids, conjunctiva, and cornea.
Natamycin is used as eyedrops.
Natamycin is also used in the food industry as a preservative.
Allergic reactions may occur. It is unclear if medical use during pregnancy or breastfeeding is safe.
Natamycin is in the macrolide and polyene families of medications.
Natamycin results in fungal death by altering the cell membrane.
Natamycin was discovered in 1955 and approved for medical use in the United States in 1978.
Natamycin is on the World Health Organization's List of Essential Medicines.
Natamycin is produced by fermentation of certain types of the bacterium Streptomyces.
Natamycin is a polyene antibiotic that generally finds application as an antifungal agent as it lacks development of resistance and has a broad spectrum of activity.
However, its mode of action is yet unclear, direct binding and isothermal titration calorimetry studies has revealed that natamycin binds specifically to ergosterol present in model membranes.
Natamycin shows activity against both molds and yeasts.
Natamycin finds applications as a fungicidal and antibiotic preservative in the food industry.
Natamycin is an antifungal drug for topical ophthalmic administration.
Natamycin is a tetraene polyene antibiotic derived from Streptomyces natalensis.
Natamycin possesses in vitro activity against a variety of yeast and filamentous fungi, including Candida, Aspergillus, Cephalosporium, Fusarium and Penicillium.
Although the activity against fungi is dose-related, natamycin is predominantly fungicidal.
Natamycin is not effective in vitro against gram-positive or gram-negative bacteria.
Topical administration appears to produce effective concentrations of natamycin within the corneal stroma but not in intraocular fluid.
Natamycin (Natamycin) is a polyene macrolide antibiotic produced by submerged aerobic fermentation of Streptomycesnatalensis and related species.
Fermentation is conducted for several days, and the antibiotic is isolated either by broth extraction or by extraction of the mycelium.
The activity of natamycin against yeasts and moulds, but not bacteria, makes it convenient for use in foods that undergo a ripening period after processing.
Natamycins low solubility in water and most organic solvents makes it suitable for the surface treatment of foods.
Natamycin was evaluated by the CAC(Codex Alimentarius Commission).
At its twentieth meeting, the Committee established an ADI of 0–0.3 mg/kg bw.
Natamycin is currently approved by the FDA for use on the surface of cuts and slices of cheese where the standards for such cheese provides for the use of safe and suitable mold inhibiting ingredients.
Natamycin may be applied to cheese by dipping or by spraying a liquid solution that contains 200 to 300 parts per million (ppm) of the additive.
In antimyotic food additive used to protect cheese from mold and yeast growth.
Naturally occurring in soil as a result of bacterial fermentation, Natamycin, also known as Natamycin, was discovered by DSM scientists more than 50 years ago.
Natamycin has been on the market since 1967 and is predominantly used for food preservation and in very rare cases as a treatment for fungal infections.
Natamycin is a natural preservative that has been tested extensively; the test levels in toxicity studies are well determined.
In the quantities applied to food products, there is no safety risk.
This has been evaluated and approved by main Expert Committees on Food Additives by JECFA and confirmed by EFSA and FDA.
Natamycin is a macrolide polyene antifungal agent isolated from Streptomyces species.
Unlike other polyene antifungals, natamycin does not prevent ergosterol synthesis or alter cell membrane permeability.
Natamycin has been used to study the lipid bilayer and as a fungicidal agent in agar media.
Natamycin has also been used in research on pleiotropic regulator AdpAch.
Natamycin is sparingly soluble in aqueous solution.
Natamycin is often used in clinical in vitro tests known as antimicrobial susceptibility tests or ASTs to determine their efficacy against certain bacterial species.
They are tested against gram-negative and gram-positive bacteria using panels, discs, and MIC strips by medical microbiologists.
ASTs decrease the risk of using an antibiotic against bacteria exhibiting resistance to it, and the results are used in clinical settings to determine which antibiotic(s) to prescribe for various infections.
Natamycin (Natamycin) is a polyene macrolide antibiotic produced by submerged aerobic fermentation of Streptomyces natalensis and related species.
Fermentation is conducted for several days, and the antibiotic is isolated either by broth extraction or by extraction of the mycelium.
Natamycin is used as a food additive to control the growth of yeasts and moulds on the surface of cheese and other non-sterile products, such as meat and sausages.
The activity of natamycin against yeasts and moulds, but not bacteria, makes it convenient for use in foods that undergo a ripening period after processing.
Natamycins low solubility in water and most organic solvents makes it suitable for the surface treatment of foods.
Natamycin is used topically in veterinary medicine to treat mycotic infections, such as ringworm in cattle and horses.
Previously, it was used topically against fungal infections of the skin and mucous membranes in humans.
Natamycins medical use is now confined to topical treatment of corneal fungal infections and the prevention of such infections in users of contact lens.
Natamycin is a natural antimicrobial preservative with a particularly high antimycotic activity.
Unlike some organic acids, it inhibits the growth of fungus without killing the fungi population.
Natamycin has the empirical formula C33H47NO13. It is a natural antimicrobial that is derived from Streptomyces natalensis fermentation.
In food systems, Natamycin is technically considered an antibiotic which belongs to the polyene macrolide compounds group.
Natamycins name is derived from the Natal Province in South Africa where it was discovered in 1955 in a soil sample.
Today, it is produced as a commercial food preservative.
Natamycin belongs to a naturally occurring antifungal agent produced through the fermentation of the bacterium Streptomyces natalensis.
Natamycin is a kind of macrolide polyene antifungal used for the treatment of fungal keratitis, which is a kind of eye infection.
In medical field, it can be used for the treatment of various kind of fungal infections caused by Candida, Aspergillus, Cephalosporium, Fusarium, and Penicillium.
In food industry, it can be used as a natural preservative to prevent fungal outgrowth.
Natamycins mechanism of action is through binding to the ergosterol in the plasma membrane of fungi, inhibiting the process of ergosterol-dependent fusion of vacuoles and membrane fusion, further inhibiting the fungal growth.
Natamycin also inhibit the transport of amino acid and glucose through inhibiting membrane transport proteins.
Natamycin was discovered in the 1950s. As described by Struyk et al.
A new crystalline antibiotic, Natamycin, has been isolated from fermentation broth of a culture of a Streptomyces species, isolated from a soil sample obtained near Pietermaritzburg, State of Natal, Union of South Africa.
This organism has been named Strepyomyces natalensis.
The original name "pimaracin" can be found in earlier publications but it is no longer accepted by the WHO.
Natamycin is classified as a macrolide polyene antifungal and is characterized by a macrocyclic lactone-ring with a number of conjugated carbon–carbon double bonds.
The full chemical name is 22-(3-amino-3,6-dideoxy-b-D-manno pyranosol) oxy- 1,3,26 trihydroxy-12-methyl-10-oxo-6,11,28-trioxiatri o catosa- 8,14,16,18,20-pentanene-25-carboxylic acid.
Natamycin has a low solubility in water (approximately 40 ppm), but the activity of neutral aqueous suspensions is very stable.
Natamycin is stable to heat and it is reported that heating processes for several hours at 100 C lead to only slight activity losses.
Natamycin is active against almost all foodborne yeasts and molds but has no effect on bacteria or viruses.
The sensitivity to natamycin in vitro (minimal inhibitory concentration) is in most cases below 20 ppm.
Natamycin acts by binding irreversibly with ergosterol and other sterols, which are present in the cell membranes of yeasts and vegetative mycelium of molds.
Natamycin disrupts the cell membrane and increases the cell permeability, which finally leads to cell death.
The fungicidal of natamycin is an ‘‘all-or-none’’ effect, which destroys the cell membrane of the target cells.
Due its interaction with ergosterol, which is a major constituent of fungal cells, it is unlikely that fungi will develop resistance.
So far, after many decades of use, no development of resistance has been reported. Natamycin is mostly used for surface applications, particularly for treating surfaces of hard cheese and salamitype sausages.
One of the advantages over sorbate is that even the dissolved fraction of natamycin hardly migrates into the food matrix.
Natamycin can be applied by spraying the surface (e.g. of cheese), by dipping, by applying natamycin via coating emulsions or by direct addition.
The antifungal efficacy of natamycin has been extensively studied and a substantial amount of scientific papers have been published.
Comprehensive overview articles are available. However, due to its long history of use, no data on application studies have been published recently.
Natamycin (Natamycin; Natacyn) is a polyene antibiotic obtainedfrom cultures of Streptomyces natalensis.
The natamycin structure consists of a 26-membered lactonering containing a tetraene chromophore, an α,β-unsaturatedlactone carbonyl group, three hydroxyl groups, a carboxyl group, a trans epoxide, and a glycosidically joined mycosamine.
Like the other polyene antibiotics, natamycin isamphoteric.
The smaller polyenes are fungistatic and fungicidal within thesame concentration range.
Natamycin possesses in vitro activity against severalyeasts and filamentous fungi, including Candida,Aspergillus, Cephalosporium, Penicillium, and Fusariumspp.
The drug is supplied as a 5% ophthalmic suspension intendedfor the treatment of fungal conjunctivitis, blepharitis,and keratitis.
USES OF NATAMYCIN:
Natamycin is used to treat fungal infections, including Candida, Aspergillus, Cephalosporium, Fusarium, and Penicillium.
Natamycin 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.
Natamycin lozenges are also prescribed to treat yeast infections and oral thrush.
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.
Natamycin 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 cream cheeses, 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.
As a food additive, it has E number E235.
Throughout the European Union, it is approved only as a surface preservative for certain cheese and dried sausage products.
Natamycin 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.
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.
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 sausage types.
Natamycins medical use is now confined to topical treatment of corneal fungal infections and the prevention of suchinfections in users of contact lens.
Natamycin is used topically in veterinary medicine to treat mycotic infections, such as ringworm in cattle and horses.
Previously, it was used topically against fungal infections of the skin and mucous membranes in humans.
Natamycin is used to treat fungal infections, including candida, aspergillus, and fusarium, as well as eye drops and oral agents.5% natamycin suspension is used to treat blepharitis conjunctivitis and keratitis caused by fungal infections.
Natamycin is commonly used in food products such as cheese and sausages to prevent the growth of molds and yeasts, and to naturally extend shelf life and reduce food waste. In some countries, depending on regulatory approvals, natamycin is also used in other products such as bread, cakes, beverages and yoghurt.
Natamycin is used to treat fungal eye infections.
Natamycin works by stopping the growth of certain types of fungus.
This medication treats only fungal eye infections.
Natamycin will not work for other types of eye infections.
Unnecessary use or misuse of any drug used to treat infection can lead to its decreased effectiveness.
Natamycin is a macrocyclic tetraene originally isolated from Streptomyces natalensis in 1957.
Natamycin exhibits broad spectrum antifungal activity against yeast and filamentous fungi by binding specifically to ergosterol to block fungal growth.
Unlike the related polyenes, nystatin and filipin, Natamycin does not change the permeability of the plasma membrane.
Natamycin is used in the food industry for surface treatment of cheeses as a mould inhibitor.
Natamycin is a preservative for use as a coating on the surface of italian cheeses to prevent the growth of mold or yeast.
Natamycin is tasteless, odorless, colorless, and does not penetrate the cheese.
Natamycin is very active against virtually all molds and yeasts, but does not affect bacteria, thus not affecting the ripening and flavor improvement process of cheese.
Natamycin can be applied as a dip, spray, or by other methods such as incorporation into the cheese coatings. It is used at levels ranging from 300 to 2,000 ppm.
Traditionally, a topical application of natamycin has been used to extend the shelf life of some cheeses and dried sausages.
In the US, its usage has been extended to:
-Non-standard identity yogurt
-Cottage cheese
-Sour cream
-Cream cheese
-Salad dressing
-Soft tortillas
-The surface of bread
APPLICATION OF NATAMYCIN:
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique.
Natamycin may be used as an analytical reference standard for the quantification of the analyte in wine samples using high-performance liquid chromatography coupled to electrospray ionization in positive mode high resolution mass spectrometry (HPLC-ESI-HR-MS) and reversed-phase high-performance liquid chromatography-tandem mass spectrometry technique (UHPLC-MS/MS).
Natamycin is a white to creamy-white, almost odorless, crystalline powder.
Natamycin is practically insoluble in water, in lipids and in mineral oils.
However, Natamycin is slightly soluble in ethanol, methanol, and glacial acetic acid.
Natamycin has a purity not less than 95.0% calculated on a dry basis.
Depending on the commercial production process, it may contain up to 8% moisture.
One major drawback of natamycin is its low thermal-stability.
Temperatures above 50°C virtually deactivate the functionality of this preservative as the molecule undergoes structure degradation.
For this reason, it is not recommended to add natamycin to dough or batter formulations.
Instead, Natamycin as an effective post-baking surface spray.
In addition to spraying, it can be used as a dip or by incorporation into cheese coating films.
Natamycin is used at levels ranging from 300 to 2,000 ppm.
Natamycin is active against nearly all yeasts and molds but has no effect on bacteria, protozoa or viruses.
Natamycin is active at very low concentrations: most molds are inhibited at 0.5–6.0 μg/mL, although some species require higher concentrations.
-Cleaning Products
-Cosmetics
-Food and Beverages
-Personal Care
BENEFITS OF NATAMYCIN:
-Natural and non-animal source.
-Effective against yeasts and moulds.
-Extends shelf life.
-Effective over a wide range of pH values (3-9).
-Has no effect on bacteria, making it useful for food products produced by bacterial cultures.
-Secures desired food flavor.
-Improves cost efficiency due to the low dosage rate.
-Meets consumer demands for food protected with natural antimicrobials by fully or partially replacing synthetic additives.
FUNCTION OF NATAMYCIN:
Natamycin is believed that natamycin acts by binding to ergosterol in fungal cell membranes, which results in loss of enzyme function and inhibition of cell division.
PROPERTIES OF NATAMYCIN:
-Melting point: 2000C (dec)
-alpha: D20 +278° (c = 1 in CH3COOH)
-Boiling point 952℃
-density: 1.0 g/mL at 20 °C(lit.)
-refractive index: 1.5960 (estimate)
-Fp: >110°(230°F)
-storage temperature: Keep in dark place,Inert atmosphere,2-8°C
-solubility: Soluble in DMSO
-form: aqueous suspension
-pka: pKa 4.6(50% aq. MeOEtOH) (Uncertain);8.35 (Uncertain)
-Water Solubility: 0.41g/L(21 ºC)
-Sensitive: Light Sensitive
-BRN: 1614878
-Stability: Light sensitive
CHEMICAL PROPERTIES OF NATAMYCIN:
Natamycin (more commonly known as Natamycin) belongs to the polyene macrolide group of antifungal antibiotics.
Natamycin was derived from Streptomyces natalensis or S. chattanoogensis.
In therapeutic use, Natamycin is prescribed for a variety of fungal infections, mainly topically, but some ophthalmic applications as well.
In addition to therapeutic and food use, Natamycin has applications including use as an agricultural chemical and wood preservative.
In the dry state, Natamycin is very stable, as long as it is protected from light and heat, and stability is maintained for a minimum of 1 to 2 years.
As long as aqueous suspensions are stored in a cooland dark place, they can be kept for at least six months.
Once placed on the surface of the cheese (Natamycin does not penetrate the surface of cheese as do sorbic acid salts), the antimycotic decomposes in about six weeks.
PRODUCTION OF NATAMYCIN:
Natamycin is produced by a pure culture of Streptomyces natalensis bacteria following a strictly controlled fermentation process.
After extraction, the Natamycin is centrifuged, filtered, and washed, to ensure the purity and quality of the end product.
Natamycin is available in both liquid and powder formulations and commercially sold, amongst others.
HOW DOES OF NATAMYCIN WORK:
Natamycin protects foods through a unique mechanism that targets ergosterol in the cell wall.
Natamycin is a building block of yeasts and molds, which is responsible for intracellular nutrient transport, and therefore vital for their survival.
Natamycin is not present in the outer membranes of bacteria, these remain unaffected.
MECHANISM OF ACTION OF NATAMYCIN:
Natamycin inhibits the growth of fungi by specifically binding to ergosterol present in fungal cell membranes.
Natamycin inhibits amino acid and glucose transport proteins leading to a loss of nutrient transport across the plasma membrane.
While this binding is reversible, ergosterol binding acts as a universal mechanism of fungal inhibition, allowing natamycin to act on diverse fungal pathogens from Saccharomyces yeast to Aspergillus moulds.
Natamycin is unique amongst related antifungals specifically because it does not directly cause membrane permeabilization.
Natamycin has very low solubility in water; however, natamycin is effective at very low levels.
Natamycins minimum inhibitory concentration is less than 10 ppm for most molds.
Like other polyene antibiotics, Natamycin inhibits fungal growth by binding to sterols.
Specifically, Natamycin binds to ergosterol in the plasma membrane, preventing ergosterol-dependent fusion of vacuoles, as well as membrane fusion and fission.
This differs from the mechanism of most other polyene antibiotics, which tend to work by altering fungal membrane permeability instead.
SYNONYM:
Natamycin
7681-93-8
Mycophyt
Synogil
Tennecetin
Antibiotic A-5283
UNII-8O0C852CPO
Delvocid
Myprozine
Pimafucin
Natamycine
CL 12625
Delvolan
Delvopos
Natacyn
Natafucin
CL 12,625
