Natamycin

• Catalog No.: Bio-0933
• CAS Number: 7681-93-8
• M. F.: C33H47NO13
• M. W.: 665.72518

SYNONYMS

• IUPAC name: (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-{[(2R,3S,4S,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
• IUPAC Traditional name: (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-{[(2R,3S,4S,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
• Synonyms: Myprozine; Natacyn; Pimafucin; Tennecetin; Mycophyt; Natafucin; Pimafugin; Synogil; Tymasil

DATABASE IDS

• CAS Number: 7681-93-8

PROPERTIES

• Application(s): Macrolide polyene antifungal antibiotic.
• Application(s): Used to treat fungal keratitis.
• Mechanism of Action: Binds to ergosterol in the plasma membrane, preventing ergosterol-dependent fusion of vacuoles, as well as membrane fusion and fission.

REFERENCES

• 1. te Welscher YM, Jones L, van Leeuwen MR, Dijksterhuis J, de Kruijff B, Eitzen G, Breukink E: Natamycin inhibits vacuole fusion at the priming phase via a specific interaction with ergosterol.
• Antimicrob Agents Chemother. 2010 Jun;54(6):2618-25. Epub 2010 Apr 12.
• 2. te Welscher YM, ten Napel HH, Balague MM, Souza CM, Riezman H, de Kruijff B, Breukink E: Natamycin blocks fungal growth by binding specifically to ergosterol without permeabilizing the membrane.
• J Biol Chem. 2008 Mar 7;283(10):6393-401. Epub 2007 Dec 29.