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PIMARICIN

CAS NUMBER: 7681-93-8

EC NUMBER: 231-683-5

MOLECULAR FORMULA: C33H47O13N

MOLECULAR WEIGHT: 665.7

 

Pimaricin is a macrolide antibiotic that has formula C33H47NO13, produced by several Streptomyces species including Streptomyces natalensis. 
Pimaricin exhibits broad spectrum antifungal activity and used in eye drops, and as a food preservative, and also as a postharvest biofungicide for citrus and other fruit crops. 

Pimaricin has a role as an antimicrobial food preservative, a bacterial metabolite, an apoptosis inducer, an ophthalmology drug and an antifungal agrochemical. 
Pimaricin is an antibiotic antifungal drug, a macrolide antibiotic, a polyene antibiotic, an epoxide, a dicarboxylic acid monoester and a monosaccharide derivative.

Amphoteric macrolide antifungal antibiotic from Streptomyces natalensis or S. chattanoogensis. 
Pimaricin is used for a variety of fungal infections, mainly topically.

Pimaricin is natural antifungal obtained by the fermentation of not genetically modified strain of Streptomyces natalensis. 
Active substance of Pimaricin is min 55% of  active Pimaricin.

Pimaricin 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. 

Pimaricin 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 Pimaricin against yeasts and moulds, but not bacteria, makes it convenient for use in foods that undergo a ripening period after processing. 

Pimaricins low solubility in water and most organic solvents makes it suitable for the surface treatment of foods. 
Pimaricin is used topically in veterinary medicine to treat mycotic infections, such as ringworm in cattle and horses. 

Pimaricin was used topically against fungal infections of the skin and mucous membranes in humans. 
Pimaricins medical use is now confined to topical treatment of corneal fungal infections and the prevention of such infections in users of contact lens.

Pimaricin 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 Pimaricin against yeasts and moulds, but not bacteria, makes it convenient for use in foods that undergo a ripening period after processing.
Pimaricins low solubility in water and most organic solvents makes it suitable for the surface treatment of foods. 
 
At Pimaricins twentieth meeting, the Committee established an ADI of 0–0.3 mg/kg bw. 
Pimaricin 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.

Pimaricin 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.

Pimaricins medical use is now confined to topical treatment of corneal fungal infections and the prevention of suchinfections in users of contact lens. 
Pimaricin is used topically in veterinary medicine to treat mycotic infections, such as ringworm in cattle and horses. 

Pimaricin was used topically against fungal infections of the skin and mucous membranes in humans.
Pimaricin is used to treat fungal infections, including candida, aspergillus, and fusarium, as well as eye drops and oral agents.

Pimaricin suspension is used to treat blepharitis conjunctivitis and keratitis caused by fungal infections.
Pimaricin is a macrolide antibiotic agent produced by several Streptomyces strains. 

Pimaricin inhibits the growth of fungi via inhibition of amino acid and glucose transport across the plasma membrane. 
Pimaricin is a food preservative, an antifungal agent in agriculture, and is widely used for fungal keratitis research.

Pimaricin is a fungistatic antibiotic which shows promise for the preservation of a wide variety of food products. 
Pimaricin, Streptomyces chattanoogensis is an antifungal macrolide polyene that binds to cell membrane sterols. 

Investigations show that the compound predominantly binds to the main sterol in fungal and yeast membranes, ergosterol. 
Pimaricin is a building block of yeasts and molds, which is responsible for intracellular nutrient transport, and therefore vital for their survival. 

Pimaricin is not present in the outer membranes of bacteria, these remain unaffected.
Pimarcin has been used as a fungicide in agar media and CYP PimD research proposes that the epoxidiation of Pimaricin occurs through a hydroperoxoferric compound. 

Pimarcin studies reveal that the regulator PimM binds to eight promoters of Pimarcin genes and its biosynthesis is influenced by a cholesterol oxidase protein encoded by PimE.
Pimaricin is a Polyene Antimicrobial.

Pimaricin is a macrocyclic tetraene originally isolated from Streptomyces natalensis in 1957. 
Pimaricin 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, pimaricin does not change the permeability of the plasma membrane. 
Pimaricin is used in the food industry for surface treatment of cheeses as a mould inhibitor.

Pimaricin is a natural antimicrobial preservative with a particularly high antimycotic activity. 
Unlike some organic acids, Pimaricin inhibits the growth of fungus without killing the fungi population.

Pimaricin has the empirical formula C33H47NO13. 
Pimaricin is a natural antimicrobial that is derived from Streptomyces natalensis fermentation.

In food systems, Pimaricin is technically considered an antibiotic which belongs to the polyene macrolide compounds group. 
Pimaricins name is derived from the Natal Province in South Africa where it was discovered in 1955 in a soil sample.

Pimaricin is produced as a commercial food preservative.
Pimaricin is a secondary microbial metabolite which has strong antimycotic activity. 

Pimaricin is produced by fermentation of bacteria Streptomyces natalensis and closely related species. 
After fermentation, Pimaricin is concentrated and purified by filtration processes or solvent extraction, and then spray-dried.

Pimaricin is used as an approved food preservative worldwide. 
Pimaricins usage is only authorized as surface treatment for cheese and dried sausages. 

Pimaricin has GRAS status and is allowed in the cheese matrix rather than on the surface.
Pimaricin, a natural and versatile anti-fungal agent during fermentation by the bacterium Streptomyces natalensis, commonly found in soil; with little to no flavour interference.

Pimaricin is an antimycotic preservative natural substance produced by fermentation ofStreptomyces natalensis. 
Active substance of pimalac is Pimaricin. 

Pimaricin contains at least 55% active Pimaricin.
Pimaricin as a 5% suspension, was used sucessfully.

Thirteen of these patients obtained a visual result of 20/40 or better. 
These results compare favorably with a series of 20 Fusarium ulcers treated with amphotericin B prior to February 1969. 

Pimaricin was effective in eliminating the fungus in only seven patients, five of whom retained a visual acuity of 20/40 or better.
Pimaricin also known as Pimaricin is a natural antifungal, obtained from the fermentation of a not genetically modified (GMO free) strain. 

Pimaricins use is approved by the EU (food additive number E-235) and by the FDA.
Pimaricin contains 50% lactose and 50% Pimaricin, which prevents the formation of moulds and yeasts on the surface. 

Unlike other antimicrobial agents, Pimaricin does not affect the appearance, taste or colour of products. 
Pimaricin is the active component in PIMARICIN. 

Pimaricin has been shown to be both safe and effective in lengthening the life of a wide range of food products for more than thirty years. 
Pimaricin is often used for cheese, sausages, and dried meat products.

Pimaricin is a natural antimicrobial agent, which delivers great antimicrobial activity against yeasts and moulds. 
Pimaricin shows no activity against bacteria. 

Pimaricin is widely used in food and pharmaceutical applications.
Pimaricin is a polyene macrolide antimycotic produced by Streptomyces natalensis. 

Pimaricin has been demonstrated to block fungal growth by binding to ergosterol within cell membranes. 
In use as a food preservative for many years, no resistance to pimaricin has ever been observed in Penicillium spp. populations. 

Pimaricin has potential to be an effective naturally derived fungicide for postharvest management of fruit decays when used by itself or in mixtures with conventional fungicides for improved efficacy and as an anti-resistance strategy.
Pimaricin belongs to a naturally occurring antifungal agent produced through the fermentation of the bacterium Streptomyces natalensis. 

Pimaricin is a kind of macrolide polyene antifungal used for the treatment of fungal keratitis, which is a kind of eye infection. 
Pimaricin can be used for the treatment of various kind of fungal infections caused. 

Pimaricin can be used as a natural preservative to prevent fungal outgrowth. 
Pimaricins 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. 

Pimaricin also inhibit the transport of amino acid and glucose through inhibiting membrane transport proteins. 
Pimaricin was discovered in the 1950s. 

A new crystalline antibiotic, pimaricin, 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. 
Pimaricin is classified as a macrolide polyene antifungal and is characterized by a macrocyclic lactone-ring with a number of conjugated carbon–carbon double bonds. 

Pimaricin 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.
Pimaricin has a low solubility in water, but the activity of neutral aqueous suspensions is very stable. 

Pimaricin is stable to heat and it is reported that heating processes for several hours at 100 C lead to only slight activity losses. 
Pimaricin is active against almost all foodborne yeasts and molds but has no effect on bacteria or viruses. 

The sensitivity to Pimaricin in vitro is in most cases below 20 ppm.
Pimaricin acts by binding irreversibly with ergosterol and other sterols, which are present in the cell membranes of yeasts and vegetative mycelium of molds. 

Pimaricin disrupts the cell membrane and increases the cell permeability, which finally leads. 
The fungicidal of Pimaricin is an ‘‘all-or-none’’ effect, which destroys the cell membrane of the target cells.

Due Pimaricins 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. 

Pimaricin 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 Pimaricin hardly migrates into the food matrix. 

Pimaricin can be applied by spraying the surface, by dipping, by applying Pimaricin via coating emulsions or by direct addition.
The antifungal efficacy of Pimaricin 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.
Pimaricin 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, Pimaricin is used to treat fungal infections, including Candida, Aspergillus, Cephalosporium, Fusarium, and Penicillium. Pimaricin 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. 
Pimaricin is also used in the food industry as a preservative.

Pimaricin (more commonly known as pimaricin) belongs to the polyene macrolide group of antifungal antibiotics. 
Pimaricin was derived from Streptomyces natalensis or S. chattanoogensis. 

Pimaricin is prescribed for a variety of fungal infections, mainly topically, but some ophthalmic applications as well. 
In addition to therapeutic and food use, pimaricin has applications including use as an agricultural chemical and wood preservative.

In the dry state, pimaricin 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, the antimycotic decomposes in about six weeks.
Pimaricin is a macrocyclic tetraene originally isolated from Streptomyces natalensis in 1957. 

Pimaricin 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, pimaricin does not change the permeability of the plasma membrane. 

Pimaricin is used in the food industry for surface treatment of cheeses as a mould inhibitor.

Pimaricin is a preservative for use as a coating on the surface of italian cheeses to prevent the growth of mold or yeast. 
Pimaricin is tasteless, odorless, colorless, and does not penetrate the cheese. 

Pimaricin 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. 
Pimaricin can be applied as a dip, spray, or by other methods such as incorporation into the cheese coatings. 

Pimaricin is used at levels ranging from 300 to 2,000 ppm.
Pimaricin, also known as pimaracin, belongs to the polyene family of antibiotics. 

Thus, Pimaricin may be used to retard the growth of fungi in meat products to which fermentative cultures are added, and is typically applied as a surface treatment. 
Resistant organisms are not typically encountered even though Pimaricin has been used as a food preservative for more than three decades. 

Unlike most bacteriocins, Pimaricin is toxic to eukaryotes. 
Acceptable daily intake of Pimaricin for humans is 0–0.3 mg/kg of body weight.

The spectrum of Pimaricin's activity is somewhat narrower than that of amphotericin and nystatin, but at the same time, it is less toxic. 
Pimaricin exhibits especially pronounced activity against a few strains of Fusarium and Cefalosporium. 

Pimaricin is a drug for treating superficial fungal infections, and Pimaricin is used only for ophthalmologic purposes. 
Pimaricin is a polyene antibiotic obtainedfrom cultures of Streptomyces natalensis.

The Pimaricin 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, Pimaricin isamphoteric.

The smaller polyenes are fungistatic and fungicidal within thesame concentration range.
Pimaricin possesses in vitro activity against severalyeasts.
The drug is supplied as a 5% ophthalmic suspension intendedfor the treatment.

 


USES:

-Effective prevention of yeast and mould spoilage

-Fast solubility and lower sedimentation

-Cost-efficiency

-Consumer- friendly labelling

-Increased shelf life extension

 

APPLICATION:

-Pimaricin is a white to creamy-white, almost odorless, crystalline powder.

-Pimaricin is practically insoluble in water, in lipids and in mineral oils. 

-Pimaricin is slightly soluble in ethanol, methanol, and glacial acetic acid.

-Pimaricin 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 Pimaricin is its low thermal-stability. 

-Temperatures above 50°C virtually deactivate the functionality of this preservative as the molecule undergoes structure degradation. 

-Pimaricin is not recommended to add Pimaricin to dough or batter formulations. 

-Pimaricin as an effective post-baking surface spray.

-In addition to spraying, Pimaricin can be used as a dip or by incorporation into cheese coating films. 

-Pimaricin is used at levels ranging from 300 to 2,000 ppm.

-Pimaricin is active against nearly all yeasts and molds but has no effect on bacteria, protozoa or viruses. 

-Pimaricin is active at very low concentrations: most molds are inhibited at 0.5–6.0 μg/mL, although some species require higher concentrations.

 


BENEFITS:

-Pimaricin is effective against a broad list of mould, fungi and yeast that prevents all food deterioration caused by these strains.

-Prevents formation of toxic mycotoxins.

-Improves shelf life of food products.

-Has no effect on desirable culture activity in fermented products.

-Does not affect the appearance, flavor, aroma or color of food products.

-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:

Pimaricin is believed that Pimaricin acts by binding to ergosterol in fungal cell membranes, which results in loss of enzyme function and inhibition of cell division.

 

PROPERTIES:

-Min. Purity Spec: 95% (HPLC)

-Physical Form (at 20°C): White to light yellow powder

-Melting Point: 280-300°C

 


TECHNICAL INFORMATIONS:

-Melting Point :280° C

-Boiling Point :952.17° C at 760 mmHg (Predicted)

-Density :1.39 g/cm3 (Predicted)

-Refractive Index :n20D 1.62 (Predicted)

-Optical Activity :α20/D +265.8°, c = 0.6 in Acetic Acid

-pK Values :pKa: 3.71 (Predicted), pKb: 8.12 

 

STORAGE:

Store long-term at 2-8°C

 

SYNONYM:

Natacyn
Delvocid
Delvolan
Delvopos
Myprozine
Natafucin
Pimafucin
Pimaricine
Tennecetin
7681-93-8
Antibiotic A 5283
Pimafugin
Tymasil
E235
Pimaricin (JP15)
CHEBI:7488
SCHEMBL16426505
AKOS015961926
AC-15226
AC-32601
A 5283
C08073
Pimaricin, Antibiotic for Culture Media Use Only
W-104343

 

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