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Natamycin

Natamycin structure

CAS No:
7681-93-8
Formula:
C33H47NO13
Chemical Name:
Natamycin
Synonyms:
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-β-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)-;Pimaricin;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-β-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-,[1R-(1R*,3S*,5R*,7R*,8E,12R*,14E,16E,18E,20E,22R*,24S*,25R*,26S*)]-;Tennecetin;6,11,28-Trioxatricyclo[22.3.1.05,7]octacosane,pimaricin deriv.;(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;Myprozine;Natamycin;Pimafucin;[1R-(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;δ-Natamycin;Myuprozine;CL 12625;Antibiotic A 5283;Synogil;Natacyn;Mycophyt;E 235;Natamax lactose;Natamax SF;Natamax;Delvocid;Natajen;Natamatrix;141-35-5;306-36-5;1383-95-5;1406-71-9;223558-57-4;81612-01-3
Categories:
Cosmetic Ingredient > Cosmetic Preservative

Description

Natamycin (pimaricin) is an antifungal macrolide polyene that binds to cell membrane sterols.Target: AntifungalNatamycin (INN), also known as pimaricin and sometimes sold as Natacyn, is a naturally occurring antifungal agent produced during fermentation by the bacterium Streptomyces natalensis, commonly found in soil. Natamycin has a very low solubility in water; however, natamycin is effective at very low levels. There is an MIC (minimum inhibitory concentration) of less than 10 ppm for

Natamycin Basic Attributes

Molecular Weight：

665.73

Exact Mass：

665.73

EC Number：

231-683-5

DSSTox ID：

DTXSID6021163

HScode：

29419090

Characteristics

PSA：

231

XLogP3：

1.1

Appearance：

aqueous suspension

Density：

1.4±0.1 g/cm3

Melting Point：

290 °C (decomp)

Boiling Point：

952℃

Flash Point：

>110°(230°F)

Refractive Index：

1.620

Water Solubility：

soluble in DMSO

Storage Conditions：

2-8°C

Toxicity：

LD50 orally in male, female rats (g/kg): 2.73, 4.67 (Levinskas)

Specific rotation：

D20 +278° (c = 1 in CH3COOH)

PH：

5,5-7,5 (1 % w/v solution in previously neutralised mixture of 20 parts dimethylformamide and 80 parts of water)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

24/25-36

RTECS Number：

TK3325000

Marks：

Stability/Shelf Life：

Light sensitive

Natamycin Use and Manufacturing

Methods of Manufacturing

It is produced by controlled fermentation of Streptomyces natalensis.

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.

Use Classification：

Food Additives -> PRESERVATIVE; -> JECFA Functional Classes

Food Additive Classes：

Food Additives -> PRESERVATIVE;

Computed Properties

Molecular Weight:665.7
XLogP3:-1.3
Hydrogen Bond Donor Count:7
Hydrogen Bond Acceptor Count:14
Rotatable Bond Count:3
Exact Mass:665.30474055
Monoisotopic Mass:665.30474055
Topological Polar Surface Area:231
Heavy Atom Count:47
Complexity:1220
Defined Atom Stereocenter Count:13
Undefined Atom Stereocenter Count:1
Undefined Bond Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Natamycin is a tetraene polyene antibiotic extracted from Streptomyces natalensis. It has in vitro activity against a variety of yeasts and filamentous fungi, including Candida, Aspergillus, Cephalosporin, Fusarium and True molds. Its mechanism of action is that the drug molecules bind to the sterol part of the fungal cell membrane to form a polyene sterol complex, which changes the permeability of the cell membrane and causes the depletion of basic cell components in the fungal cell. Although this antifungal effect is dose-dependent, natamycin is still a significant fungicide. Natamycin has no effect on Gram-positive and Gram-negative bacteria in vitro. Topical application of natamycin can reach effective concentrations in the corneal stroma, but not in the intraocular fluid. Topical drops of 5% natamycin are unlikely to be absorbed systemically. Like other polyene antibiotics, the amount of the drug absorbed through the gastrointestinal tract is very small. The results of a study on rabbit drops of natamycin showed that the drug could not be detected in the aqueous humor and serum, but the sensitivity of the measurement did not exceed 2mg/ml. Carcinogenicity, Mutagenicity and Reproductive Toxicity: There is no long-term evaluation data on the carcinogenicity, mutagenicity and reproductive toxicity of natamycin in animals.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Natamycin eye drops
Ingredients	The main ingredient of this tablet is natamycin, whose chemical name is 22-[(3-amino-3,6-dideoxy-beta;-D-pyranosyl)oxy]-1,3,26-trihydroxy-12methyl-10-oxo-6,11,28-trioxacyclo[22.3.1.05.7]dioctadecyl-8,14,16,18,20-pentaene-25-carboxylic acid.
Indication	Not yet clear.
Specifications	15 ml: 0.75 g

Natamycin eye drops
Ingredients	The main ingredient of this tablet is natamycin, whose chemical name is 22-[(3-amino-3,6-dideoxy-beta;-D-pyranosyl)oxy]-1,3,26-trihydroxy-12methyl-10-oxo-6,11,28-trioxacyclo[22.3.1.05.7]dioctadecyl-8,14,16,18,20-pentaene-25-carboxylic acid.
Indication	Not yet clear.
Specifications	10ml:500mg
Manufacturer	North China Pharmaceutical Company.Ltd

natamycin

See More Related Drugs

Registered Holders

North China Pharmaceutical Huasheng Co., Ltd.

China
Active
Beijing Yimin Pharmaceutical Co., Ltd.

China
Active
SHANDONG FREDA BIOTECHNOLOGY CO LTD

United States
Active

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