| Description |
Pimaricin (also known as natamycin, INN) belongs to a naturally occurring antifungal agent produced through the fermentation of the bacterium Streptomyces natalensis. It 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. Its 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. It also inhibit the transport of amino acid and glucose through inhibiting membrane transport proteins. |
| References |
https://jk-ingredients.en.made-in-china.com
https://www.drugbank.ca/drugs/DB00826 |
| Description |
Natamycin was discovered in the 1950s. As described by Struyk et al. 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 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 [22.3.1.05.7] 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. It 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. |
| Chemical Properties |
Natamycin (more commonly known as pimaricin) belongs to the polyene macrolide group of antifungal antibiotics. It was derived from Streptomyces natalensis or S. chattanoogensis. In therapeutic use, it 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 (pimaricin does not penetrate the surface of cheese as do sorbic acid salts), the antimycotic decomposes in about six weeks. |
| Chemical Properties |
White to Off-White Solid |
| Uses |
Polyene antifungal antibiotic |
| Uses |
analgesic, antimigraine |
| Uses |
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. |
| Uses |
Pimaricin is a preservative for use as a coating on the surface of italian cheeses to prevent the growth of mold or yeast. It is tasteless, odorless, colorless, and does not penetrate the cheese. It 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. It 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. |
| Uses |
Natamycin (l), from Streptomyces nataIensis and Streptomyces chat tanoogensis, is used for the control of diseases of bulbs. |
| Brand name |
Natacyn (Alcon). |
| General Description |
Natamycin (pimaricin; 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. |
| Safety Profile |
Poison by intravenous, intramuscular, subcutaneous, and intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx. Used as an antibacterial agent. |
| Veterinary Drugs and Treatments |
Natamycin is a semisynthetic polyene antibiotic. Natamycin is poorly water-soluble and will not penetrate the intact corneal epithelium. Natamycin is the only antifungal agent approved for use on the eye and the only commercially available eye drug for treatment of fungal keratitis. |
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