| Size | Price | Stock | Qty |
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| ln Vitro |
Natamycin is a macrolide antibiotic that is effective against S. natalensis, S. gilvosporeus, S. lydicus, and S. chattanoogensis. It inhibits fungal growth by inhibiting regulation and maybe transport across the plasma membrane. Natamycin is widely utilized in the food sector and as a medicine for topical applications. Natamycin's mechanism of action differs from those of other polyene antibiotics in that it does not rely on ergotol to permeabilize the plasma membrane. The abrupt stop of yeast growth after natamycin treatment suggests that natamycin has a transitory action, most likely at the plasma membrane level [1][2].
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Systemic absorption should not be expected following topical administration, and as with other polyene antibiotics, absorption from the gastrointestinal tract is very poor. |
| References | |
| Additional Infomation |
Natamycin is a Polyene Antimicrobial.
Natamycin has been reported in Streptomyces gilvosporeus, Streptomyces, and other organisms with data available. 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. Amphoteric macrolide antifungal antibiotic from Streptomyces natalensis or S. chattanoogensis. It is used for a variety of fungal infections, mainly topically. Drug Indication For the treatment of fungal blepharitis, conjunctivitis, and keratitis caused by susceptible organisms including Fusarium solani keratitis. Mechanism of Action 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. Pharmacodynamics 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. |
| Molecular Formula |
C33H47NO13
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|---|---|
| Molecular Weight |
665.7252
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| Exact Mass |
665.304
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| CAS # |
7681-93-8
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| PubChem CID |
5284447
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
952.2±65.0 °C at 760 mmHg
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| Melting Point |
2000ºC
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| Flash Point |
529.7±34.3 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.620
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| LogP |
0.74
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| Hydrogen Bond Donor Count |
7
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| Hydrogen Bond Acceptor Count |
14
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
47
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| Complexity |
1220
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| Defined Atom Stereocenter Count |
14
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| 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
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| InChi Key |
NCXMLFZGDNKEPB-FFPOYIOWSA-N
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| InChi Code |
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
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| Chemical Name |
(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
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~16.67 mg/mL (~25.04 mM)
H2O : ~1 mg/mL (~1.50 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.67 mg/mL (2.51 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.67 mg/mL (2.51 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.5021 mL | 7.5106 mL | 15.0211 mL | |
| 5 mM | 0.3004 mL | 1.5021 mL | 3.0042 mL | |
| 10 mM | 0.1502 mL | 0.7511 mL | 1.5021 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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