Natamycin

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.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: Z10-101-166

CAS No:7681-93-8

Synonyms/Alias:Pimaricin;Tennecetin; Myprozine;

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M.F/Formula
C33H47NO13
M.W/Mr.
665.73
Labeling Target
30s ribosomal subunit
Application
Natamycin is an antifungal drug for topical ophthalmic administration. It is a tetraene polyene antibiotic derived from Streptomyces natalensis. It 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.
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Biological Activity
Natamycin (Pimaricin) is a macrolide antibiotic agent produced by several Streptomyces strains. Natamycin inhibits the growth of fungi via inhibition of amino acid and glucose transport across the plasma membrane.
Areas of Interest
Immunology & Inflammation
Cell Biology
Cancer
Functions
Natamycin is used for a variety of fungal infections, mainly topically.

Natamycin is a polyene macrolide antifungal compound produced by certain strains of Streptomyces natalensis and related actinomycetes. Structurally characterized by a large lactone ring and multiple conjugated double bonds, natamycin exhibits high specificity for ergosterol-containing membranes, making it a valuable tool for probing fungal cell biology. Its unique biochemical properties and selective mechanism of action have established natamycin as an essential agent in the study of fungal physiology, membrane biochemistry, and antifungal resistance. Researchers and industrial technologists utilize natamycin for its ability to inhibit a broad spectrum of filamentous fungi and yeasts, thereby supporting a range of investigative and quality control applications in both academic and applied settings.

Antifungal mechanism studies: Natamycin is widely employed to investigate the molecular basis of antifungal activity, particularly its interaction with ergosterol in fungal cell membranes. Unlike other polyenes that induce membrane permeabilization, natamycin binds specifically to ergosterol without causing significant disruption of membrane integrity. This distinct mode of action allows researchers to dissect the roles of sterol-binding versus membrane-disrupting antifungals, providing insights into the structure-activity relationships that govern polyene efficacy and selectivity.

Membrane biochemistry research: Due to its selective affinity for ergosterol, natamycin serves as a precise biochemical probe for studying sterol composition and function within biological membranes. It enables the differentiation of ergosterol-dependent processes from those involving other sterols, facilitating detailed analyses of membrane organization, lipid-protein interactions, and the impact of sterol modulation on cellular physiology. These studies are critical for advancing the understanding of fungal cell biology and the development of novel antifungal strategies.

Fungal contamination control in laboratory settings: The potent antifungal properties of natamycin make it a preferred additive in media formulations designed to suppress unwanted fungal growth during microbiological experiments. Its inclusion in culture media helps maintain the integrity of bacterial, algal, or plant cell cultures by selectively inhibiting filamentous fungi and yeasts, thereby reducing experimental variability and ensuring reproducibility in sensitive research protocols.

Screening and resistance studies: Natamycin is frequently utilized in antifungal susceptibility testing and resistance profiling of clinical and environmental fungal isolates. By serving as a reference compound in in vitro assays, it enables the assessment of sensitivity patterns, detection of resistance phenotypes, and evaluation of cross-resistance with other polyene agents. These applications support the ongoing surveillance of antifungal resistance and inform the rational design of next-generation antifungal compounds.

Quality assurance in industrial biotechnology: In bioprocessing environments where fungal contamination poses a threat to product quality and yield, natamycin is applied as a control agent to safeguard fermentation processes, enzyme production, and other biotechnological workflows. Its targeted activity against fungi, coupled with minimal impact on bacterial and mammalian systems, makes it an effective tool for maintaining contamination-free operations and enhancing the reliability of industrial-scale production systems.

Long-term Storage Conditions
Soluble in DMSO
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Short-term Storage Conditions
Dry, dark and at 0 - 4 °C
Solubility
-20 °C
InChI
InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1
InChI Key
NCXMLFZGDNKEPB-FFPOYIOWSA-N
Isomeric SMILES
C[C@@H]1C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@@H]3[C@H](O3)/C=C/C(=O)O1)O)O)O)C(=O)O)O[C@H]4[C@H]([C@H]([C@@H]([C@H](O4)C)O)N)O
BoilingPoint
897.6±65.0 °C at 760 mmHg
Melting Point
160-180ºC

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