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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.
Natamycin can be used for the treatment of various kind of fungal infections caused by Candida, Aspergillus, Cephalosporium, Fusarium, and Penicillium.
CAS Number: 7681-93-8
Molecular Formula: C33H47NO13
Molecular Weight: 665.73
EINECS Number: 231-683-5
Synonyms: NATAMYCIN, pimaricin, 7681-93-8, Myprozine, Pimafucin, Tennecetin, Natacyn, Natamicina, Natamycine, Delvocid, Mycophyt, Pimaracin, Synogil, Natamycinum, Antibiotic A-5283, Delvolan, Pimaricine, Pimarizin, CL 12,625, 8O0C852CPO, INS NO.235, INS-235, NSC-759167, CL 12625, CL-12625, DTXCID301163, DTXSID6021163, E-235, 16-(3-Amino-3,6-didesoxy-beta-D-mannopyranosyloxy)-5,6-epoxy-8,12,14-trihydroxy-26-methyl-2,10-dioxo-1-oxacyclohexacosa-3,17,19,21,23-pentaen-13-carbonsaeure, CHEBI:7488, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-((2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl)oxy-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, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-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, RefChem:56874, DTXCID501473823, (1R,3S,5R,7R,12R,22R,24S,25R,26S)-22-(((3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl)oxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo(22.3.1.0^(5,7))octacosa-8,14,16,18,20-pentaene-25-carboxylic acid, (1R*,3S*,5R*,7R*,8E,12R*,14E,16E,18E,20E,22R*,24S*,25R*,26S*)-22-(3-Amino-3,6-dideoxy-beta-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, 231-683-5, 6,11,28-Trioxatricyclo(22.3.1.05,7)octacosa-8,14,16,18,20-pentaene-25-carboxylic acid, 22-((3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy)-1,3,26-trihydroxy-12-methyl-10-oxo-, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-, DTXSID201015573, MFCD00135085, Delvopos, Natafucin, Natamycin(Pimaricin), C33H47NO13, Tymasil, 6,11,28-Trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid, 22-[(3-amino-3,6-dideoxy-.beta.-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-, Pimarizin [German], Natamycine [INN-French], Natamycinum [INN-Latin], Natamicina [INN-Spanish], UNII-8O0C852CPO, Tennecetin, Myprozine, Natafucin, Pimafucin, Pimafugin, Mycophyt, Natacyn, Synogil, Natamycin [USAN:USP:INN:BAN], NCGC00016686-01, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0~5,7~]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid, 6,11,28-TRIOXATRICYCLO(22.3.1.05,7)OCTACOSA-8,14,16,18,20-PENTAENE-25-CARBOXYLIC ACID, 22-((3-AMINO-3,6-DIDEOXY-.BETA.-D-MANNOPYRANOSYL)OXY)-1,3,26-TRIHYDROXY-12-METHYL-10-OXO-, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-, CAS-7681-93-8, EINECS 231-683-5, Pimaricin, Natamycin, Natamycin (Standard), NATAMYCIN [FCC], NATAMYCIN [INN], PIMARICIN [JAN], NATAMYCIN [MI], NATAMYCIN [USAN], NATAMYCIN [VANDF], NATAMYCIN [MART.], NATAMYCIN [USP-RS], NATAMYCIN [WHO-DD], SCHEMBL18140, orb1310363, orb3025289, NATAMYCIN [ORANGE BOOK], CHEMBL1200656, HY-B0133R, MSK2531, NATAMYCIN [USP MONOGRAPH], NCXMLFZGDNKEPB-FFPOYIOWSA-N, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-(((2R,3S,4S,5S,6R)-4-Amino-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-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, EX-A1989, HY-B0133, Tox21_110561, BDBM50370755, EBC-27421, AKOS030485970, 73 - Natamycin (pimaricin) in cheese, AN26164, CS-1909, DB00826, NSC 759167, NICOTINAMIDE_ADENINE_DINUCLEOTIDE, Stereoisomer of 22-((3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo(22.3.1.0(sup 5,7))octacosa-8,14,16,18,20-pentaene-25-carboxylic acid, NS00003340, Natamycin, VETRANAL(TM), analytical standard, NCGC00373238-02_C33H47NO13_Delvocid, EN300-22411493, Pimaricin preparation, ~2.5%, aqueous suspension, Q248466, Natamycin, United States Pharmacopeia (USP) Reference Standard, Pimaricin, from Streptomyces chattanoogensis, >=95% (HPLC), Natamycin, Pharmaceutical Secondary Standard; Certified Reference Material, (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-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, NataMycin, A 5283, Delvolan, Delvocid, Myprozine, Natacyn, Natafucin, PiMafucin, PiMafugin, A5263, CL 12625, E235;Natamycin(FermentionProcess);(1R*,3S*,5R*,7R*,8E,12R*,14E,16E,18E,20E,22R*,24S*,25R*,26S*)]-22-[(3-Amino-3,6-dideoxy-β-D-mannopyranosyl)oxy]-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;NATAMYCIN;PIMAFUCIN;PIMARICIN, STREPTOMYCES CHATTANOOGENSIS;antibiotica-5283;pimarizin
Natamycin 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.
Natamycin 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, also known as pimaricin, 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.
Natamycin is a polyene antifungal compound, widely used as a food preservative and pharmaceutical antifungal agent to inhibit the growth of molds and yeasts.
Natamycins chemical formula is C₃₃H₄₇NO₁₃.
It belongs to the class of macrolide polyene antibiotics.
Chemically, natamycin consists of a large macrocyclic lactone ring with multiple conjugated double bonds (polyene structure).
Natamycin also contains functional groups such as hydroxyls and a mycosamine sugar moiety.
This structure is responsible for its antifungal activity.
Physically, natamycin appears as a white to off-white crystalline powder.
Natamycin is poorly soluble in water but can be dispersed in aqueous systems.
It is sensitive to light and oxidation.
Natamycin exhibits strong antifungal activity, particularly against molds and yeasts.
Natamycin binds to ergosterol in fungal cell membranes.
This disrupts membrane function.
Natamycin is highly specific to fungi, with minimal activity against bacteria.
This makes it suitable for targeted preservation.
Natamycin helps control fungal contamination without affecting other microorganisms.
Natamycin is chemically stable under neutral conditions, but can degrade when exposed to light, oxygen, or extreme pH.
Proper storage is required.
Natamycin is often protected from light.
It is widely used in food preservation and pharmaceutical applications due to its effectiveness and safety.
Natamycin helps extend shelf life of products.
This highlights its importance.
Natamycin is best described as a natural antifungal agent with selective activity against molds and yeasts, used for preservation and infection control in food and medical applications.
Melting point: 2000C (dec)
alpha: D20 +278° (c = 1 in CH3COOH)
Boiling point: 952℃
Density: 1.0 g/mL at 20 °C (lit.)
bulk density: 200 kg/m³
refractive index: 1.5960 (estimate)
Flash point: >110° (230°F)
storage temp.: 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)
color: Cream colored
Water Solubility: 0.41 g/L (21 ºC)
Sensitive: Light Sensitive
Merck: 13,6453
BRN: 1614878
Stability: Light sensitive
Major Application: cleaning products; cosmetics; food and beverages; personal care
Cosmetics Ingredients Functions: PRESERVATIVE; ANTIMICROBIAL
InChIKey: NCXMLFZGDNKEPB-FFPOYIOWSA-N
SMILES: C[C@@H]1CC=CC=CC=CC=C[C@@H](C[C@@H]2OC@
(CC@@H
C[C@H]3O[C@@H]3C=CC(=O)O1)CC@H
[C@H]2C(O)=O)O[C@@H]4OC@H
C@@H
C@H
[C@@H]4O
LogP: 0.880 (est)
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.
Natamycin 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 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, natamycin is used to treat fungal infections, including Candida, Aspergillus, Cephalosporium, Fusarium, and Penicillium.
Natamycin 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.
Natamycin is also used in the food industry as a preservative.
Natamycin, also known as pimaracin, belongs to the polyene family of antibiotics; (a group of antifungal agents which target and bind to eukaryotic sterols and specifically ergosterol), and it is a secondary metabolite of Streptomyces natalensis.
Very low levels (10–20 ppm) are needed to inhibit almost all yeasts and molds, while no amount of natamycin is sufficient to inhibit most bacteria, as they lack the sterol targeted by natamycin (some gram-positive types may be susceptible).
Thus, natamycin 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 (i.e., dip or spray).
Resistant organisms are not typically encountered even though natamycin has been used as a food preservative for more than three decades.
Unlike most bacteriocins, natamycin is toxic to eukaryotes.
Natamycin is produced by fermentation using the microorganism Streptomyces natalensis.
Natamycin is a naturally derived compound.
This makes it suitable for food applications.
Natamycin exhibits a polyene structure with conjugated double bonds, which interact with sterols in fungal membranes.
This interaction disrupts membrane integrity.
Natamycin inhibits fungal growth without fully lysing cells.
Natamycin shows very low systemic absorption when ingested or applied topically.
It remains mostly on the surface where it is applied.
This contributes to its safety profile.
It is effective at very low concentrations, typically in the ppm range.
Small amounts are sufficient to inhibit fungal growth.
This improves efficiency and cost-effectiveness.
Natamycin is often used as a surface preservative, rather than being mixed deeply into products.
Natamycin remains active on the surface where contamination occurs.
This is important in food preservation.
The compound is sensitive to ultraviolet light and oxidation, which can reduce its activity.
Natamycin is usually stored in light-protective packaging.
This maintains effectiveness.
Natamycin does not significantly affect taste, odor, or texture of treated products.
Natamycin is considered organoleptically neutral.
This is important in food applications.
It shows low potential for resistance development compared to some antifungals, especially in food-related use.
Natamycins mechanism is specific and effective.
This supports long-term use.
Natamycin is a naturally derived, highly effective, and surface-active antifungal agent with low absorption and minimal sensory impact, making it ideal for food preservation and topical applications.
Uses Of Natamycin:
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, pimaricin 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 widely used in the food industry as a preservative (E235) to inhibit the growth of molds and yeasts.
It is commonly applied to cheese surfaces.
This extends shelf life without affecting flavor.
In cheese and dairy products, it is used as a surface treatment.
It prevents fungal spoilage during storage.
This maintains product quality.
Natamycin is applied in baked goods and pastries to control mold growth.
It helps keep products fresh for longer.
This improves shelf stability.
In processed meats and sausages, it is used to inhibit surface mold formation.
Natamycin protects products during curing and storage.
Natamycin is used in beverages, such as fruit juices and wines, to control yeast and mold contamination.
It helps maintain product stability.
This prevents spoilage.
In pharmaceutical applications, natamycin is used as a topical antifungal medication.
Natamycin treats fungal infections of the skin, eyes, and mucous membranes.
This supports medical treatment.
Natamycin is applied in eye drops (ophthalmic formulations) to treat fungal eye infections.
It is effective against ocular fungi.
This is important in clinical use.
Natamycin is used in cosmetic formulations to control microbial contamination.
It helps preserve product integrity.
This improves shelf life.
Natamycin is also applied in surface coatings and packaging treatments to inhibit fungal growth.
It protects products during storage.
Natamycin is used wherever targeted antifungal protection against molds and yeasts is required, especially in food preservation, pharmaceuticals, and surface treatments.
Natamycin is used in ripened and specialty cheeses to control unwanted mold growth while allowing desired cultures to develop.
Natamycin helps maintain product authenticity.
This preserves quality during aging.
In dry-cured meat products, it is applied to prevent surface fungal contamination.
Natamycin protects products during long curing periods.
This improves shelf stability.
It is used in ready-to-eat and packaged foods as a surface preservative.
It inhibits mold growth during storage and transport.
This enhances product safety.
In fruit and vegetable coatings, natamycin can be applied to reduce fungal spoilage.
Natamycin helps extend freshness.
Natamycin is applied in fermented food systems to control unwanted fungal species.
Natamycin allows beneficial microorganisms to function while suppressing spoilage organisms.
This supports controlled fermentation.
In pharmaceutical creams and ointments, it is used to treat fungal skin infections.
Natamycin provides localized antifungal action.
This supports topical therapy.
Natamycin is used in veterinary medicine for treating fungal infections in animals.
Natamycin helps control infections on skin or mucous membranes.
This supports animal health.
Natamycin is applied in food packaging technologies, such as antimicrobial films or coatings.
Natamycin provides surface protection against fungi.
This enhances preservation systems.
In export-oriented food products, it helps ensure stability during long transportation periods.
Natamycin reduces spoilage risk.
This supports global distribution.
Natamycin is used wherever surface-level antifungal protection, extended shelf life, and targeted mold and yeast control are required across food, pharmaceutical, and packaging applications.
Safety Profile Of Natamycin:
Poison by intravenous, intramuscular, subcutaneous, and intraperitoneal routes.
Moderately toxic by ingestion when heated to decomposition it emits toxic fumes of NOx.
Natamycin is used as an antibacterial agent.
Natamycin presents low hazard potential, especially when used in approved food and pharmaceutical applications, due to its low systemic absorption and targeted antifungal activity.
Natamycin is generally regarded as safe at permitted levels.
However, handling of concentrated material requires precautions.
Skin contact is typically low risk, but prolonged exposure to concentrated powder may cause mild irritation.
Sensitive individuals may experience slight redness.
Protective gloves are recommended in industrial settings.
Eye contact may cause mild irritation.
Symptoms can include redness and discomfort.
Eyes should be rinsed thoroughly with water if exposure occurs.
Inhalation of dust may cause respiratory irritation.
Fine particles can irritate the nose and throat.
Adequate ventilation and dust control are important.
Ingestion is considered safe at regulated food-use levels, but large amounts may cause gastrointestinal discomfort.
Natamycin is not intended for excessive intake.
Medical advice should be sought if necessary.
Natamycin is not flammable, but it may decompose under high temperatures.
Thermal decomposition can produce carbon oxides and nitrogen-containing fumes.
Standard fire safety precautions should be followed.
Natamycin is chemically sensitive to light and oxidation, which can reduce its effectiveness.
