NATAMYCIN

PRODUCT IDENTIFICATION

CAS NO. 7681-93-8NATAMYCIN
EINECS NO. 231-683-5
FORMULA C33H47NO13
MOL WT. 665.73

TOXICITY

Oral Rat LD50: 2730mg/kg

H.S. CODE

2941.90.1010
SYNONYMS Natamycin
16-(3-Amino-3,6-didesoxy-beta-D-mannopyranosyloxy)-5,6-epoxy-8,12,14- trihydroxy-26-methy l-2,10-dioxo-1- oxacyclohexacosa-3,17,19,21,23-pentaen- 13-carbonsaeure; Delvocid; Delvolan; Delvopos; Mycophyt; Myprozine; Natacyn; Natafucin; Natamicina; Natamycin; Natamycine; Natamycinum; Pimafucin; Pimaricine; Pimarizin; Tennecetin; Pimaricin
SMILES C([C@@H]1[C@@H]2O[C@@](C[C@@H](C[C@@H]3[C@@H](C= CC(O[C@@H](C)CC=CC=CC=CC=C[C@@H](C2)O[C@H]2[C@H] ([C@H]([C@H](O)[C@@H](O2)C)N)O)=O)O3)O)(O)C[C@@H]1O) (O)=O

CLASSIFICATION

Fungicide, Bactericide, Preservative

EXTRA NOTES

Amphoteric macrolide antifungal antibiotic from Streptomyces natalensis or S. chattanoogensis. It is used for a variety of fungal infections, mainly topically
An antifungal polyene macrolide that binds specifically to ergosterol and blocks fungal growth. However, unlike nysatin and filipin, pimaricin does not change the permeability of the plasma membrane 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE

white to yellowish crystalline powder

MELTING POINT

290 C

BOILING POINT

 

SPECIFIC GRAVITY  
SOLUBILITY IN WATER

Soluble (4100 mg/l at 21 C)

SOLVENT SOLUBILITY

 

pH  
VAPOR DENSITY

 

log P -3.67 (Octanol-water)
OH RATE CONSTANT 4.18E-10 (cm3/molecule-sec at 25 C Atmospheric)

REFRACTIVE INDEX

 

NFPA RATINGS

 

FLASH POINT

 

STABILITY Stable under normal conditions.

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking

Google Scholar Search

Drug Information Portal (U.S. National Library of Medicine) - Natamycin

http://aem.asm.org/
The antifungal antibiotic natamycin belongs to the family of polyene antibiotics. Its antifungal activity arises via a specific interaction with ergosterol in the plasma membrane (te Welscher et al., J. Biol. Chem. 283:6393-6401, 2008). However, this activity does not involve disruption of the membrane barrier function, a well-known property of other members of the polyene antibiotic family, such as filipin and nystatin. Here we tested the effect of natamycin on vacuole membrane fusion, which is known to be ergosterol dependent. Natamycin blocked the fusion of isolated vacuoles without compromising the barrier function of the vacuolar membrane. Sublethal doses of natamycin perturbed the cellular vacuole morphology, causing the formation of many more small vacuolar structures in yeast cells. Using vacuoles isolated from yeast strains deficient in the ergosterol biosynthesis pathway, we showed that the inhibitory activity of natamycin was dependent on the presence of specific chemical features in the structure of ergosterol that allow the binding of natamycin. We found that natamycin inhibited the priming stage of vacuole fusion. Similar results were obtained with nystatin. These results suggest a novel mode of action of natamycin and perhaps all polyene antibiotics, which involves the impairment of membrane fusion via perturbation of ergosterol-dependent priming reactions that precede membrane fusion, and they may point to an effect of natamycin on ergosterol-dependent protein function in general.

http://www.jbc.org/content/
Natamycin is a polyene antibiotic that is commonly used as an antifungal agent because of its broad spectrum of activity and the lack of development of resistance. Other polyene antibiotics, like nystatin and filipin are known to interact with sterols, with some specificity for ergosterol thereby causing leakage of essential components and cell death. The mode of action of natamycin is unknown and is investigated in this study using different
in vitro and in vivo approaches. Isothermal titration calorimetry and direct binding studies revealed that natamycin binds specifically to ergosterol present in model membranes. Yeast sterol biosynthetic mutants revealed the importance of the double bonds in the B-ring of ergosterol for the natamycin-ergosterol interaction and the consecutive block of fungal growth. Surprisingly, in strong contrast to nystatin and filipin, natamycin did not change the permeability of the yeast plasma membrane under conditions that growth was blocked. Also, in ergosterol containing model membranes, natamycin did not cause a change in bilayer permeability. This demonstrates that natamycin acts via a novel mode of action and blocks fungal growth by binding specifically to ergosterol.

http://cms2.unige.ch/
Natamycin is a polyene antibiotic that is commonly used as an antifungal agent because of its broad spectrum of activity and the lack of development of resistance. Other polyene antibiotics, like nystatin and filipin are known to interact with sterols, with some specificity for ergosterol thereby causing leakage of essential components and cell death. The mode of action of natamycin is unknown and is investigated in this study using different in vitro and in vivo approaches. Isothermal titration calorimetry and direct binding studies revealed that natamycin binds specifically to ergosterol present in model membranes. Yeast sterol biosynthetic mutants revealed the importance of the double bonds in the B-ring of ergosterol for the natamycin-ergosterol interaction and the consecutive block of fungal growth. Surprisingly, in strong contrast to nystatin and filipin, natamycin did not change the permeability of the yeast plasma membrane under conditions that growth was blocked. Also, in ergosterol containing model membranes, natamycin did not cause a change in bilayer permeability. This demonstrates that natamycin acts via a novel mode of action and blocks fungal growth by binding specifically to ergosterol.

SALES SPECIFICATION

APPEARANCE

white to yellowish crystalline powder

PURITY

95.0% min

LOSS ON DRYING

6.0 ~ 9.0%

OPTICAL ROTATION

+276° ~ +280°

HEAVY METALS

10ppm max

LEAD

5ppm max

ARSENIC

3ppm max

MERCURY

1ppm max

pH

5.0 ~ 7.0

TOTAL PLATE COUNT

10 Cfu/g max

PATHOGEN

Absent

E. COLI

Negative

SAMONELLA

Negative

TRANSPORTATION
PACKING
 
HAZARD CLASS  
UN NO. Not regulated
PRICE INFORMATION