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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen

12 Issues per year


IMPACT FACTOR 2017: 5.294

CiteScore 2017: 3.42

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1365-3075
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Volume 79, Issue 4

Issues

Discovery of micafungin (FK463): A novel antifungal drug derived from a natural product lead

Akihiko Fujie
  • Corresponding author
  • Fermentation Research Laboratories, Astellas Pharma Inc., 5-2-6 Tokodai, Tsukuba, Ibaraki 300-2698, Japan
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/pac200779040603

FR901379, which is a novel, water-soluble, echinocandin-like lipopeptide, was isolated from a microbial culture broth. It showed potent in vivo antifungal activity against Candida albicans and inhibits the synthesis of 1,3-β-glucan. However, this compound had hemolytic activity and was also less active against Aspergillus fumigatus. To overcome these shortcomings, we synthesized FR131535 bearing an octyloxybenzoyl acyl side chain instead of a fatty acid. FR131535 retained the original activity displayed by FR901379, acquired potent anti-Aspergillus activity, and its hemolytic activity was significantly reduced. Further extensive chemical modification of FR901379 has led to the discovery of micafungin (FK463), which is effective against Candida and Aspergillus spp. Micafungin has been marketed in Japan and the United States as a candin-class parenteral antifungal agent for life-threatening mycoses.

Keywords: antifungal drugs; echinocandin; FK463; FR901379; micafungin

Conference

International Symposium on Chemistry of Natural Products (ISCNP-25) and 5th International Conference on Biodiversity (ICOB-5), International Conference on Biodiversity, International Symposium on the Chemistry of Natural Products, ICOB, ISCNP, Biodiversity, Natural Products, 25th, Kyoto, Japan, 2006-07-23–2006-07-28

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About the article

Published Online: 2009-01-01

Published in Print: 2007-01-01


Citation Information: Pure and Applied Chemistry, Volume 79, Issue 4, Pages 603–614, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac200779040603.

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