The semi-synthetic echinocandin antifungal agent,
micafungin sodium (15), is a 1,3-β-glucan synthase inhibitor
discovered by Fujisawa. It is for the treatment and
prevention of infections caused by Aspergillus and Candida
such as fungemia, respiratory mycosis and gastrointestinal
mycosis.
Micafungin is an echinocandin antifungal that inhibits 1,3-β-D-glucan synthesis. It has fungicidal activity against virtually all species of Candida, including those resistant to fluconazole, and is fungistatic against Aspergillus spp.[Cayman Chemical]
An echinocandin antifungal drug which inhibits the synthesis of 1,3-β-D-glucan, an essential component of the fungal cell wall, and represent a valuable treatment option for fungal infections.
Micafungin sodium is the salt of the semi-synthetic cyclic lipopeptide, micafungin, a member of the echinocandin class that was reported in 1999 from Fujisawa in Japan. The sodium salt takes advantage of the aryl sulphate moiety providing improved water solubility and is the preferred salt for pharmaceutical applications. Like all echinocandins, micafungin inhibits the synthesis of β-(1,3)-D-glucan, an essential component of the cell wall of susceptible fungi.
ChEBI: Micafungin sodium is an organic sodium salt and an antibiotic antifungal drug.
The key intermediate for the side chain of
micafungin (15) was prepared by regioselective 1,3-dipolar
cycloaddition reaction of 4-methoxycarbonylbenzhydroxamic
acid chloride (147) and 4-pentyloxyphenylacetylene (148)
with TEA in THF. Basic hydrolysis of thus obtained
ester 149 , followed by condensation with 1-
hydroxybenzotriazole (HOBT) gave the corresponding activated ester 150 in 95% yield. The cyclic peptide core
151, obtained by acylase-catalyzed hydrolysis of the natural
product FR901379, was acylated with 150 to give
micafungin (15) in 53% yield.
