208538-73-2

Basic information

• Product Name: Micafungin sodium
• Synonyms: Micafungin sodium;1-[(4R,5R)-4,5-Dihydroxy-N2-[4-[5-[4-(pentyloxy)phenyl]-3-isoxazolyl]benzoyl]-L-ornithine]-4-[(4S)-4-hydroxy-4-[4-hydroxy-3-(sulfooxy)phenyl]-L-threonine]pneuMocandin A0 MonosodiuM Salt;Funguard;Micafungin SodiuM(FK-463, MycaMine);Mycamine;Micafungin Sodium Salt;FK463 Sodium;Micafungin sodium Mycamine
• CAS NO: 208538-73-2
• Molecular Formula: C56H70N9O23S.Na
• Molecular Weight: 1292.27
• EINECS: 1592732-453-0
• Product Categories: API;Inhibitors
• Mol File: 208538-73-2.mol
• Article Data: 0

Chemical Properties

• Appearance: Off-White Solid
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
• Stability: Hygroscopic
• CAS DataBase Reference: Micafungin sodium(CAS DataBase Reference)
• NIST Chemistry Reference: Micafungin sodium(208538-73-2)
• EPA Substance Registry System: Micafungin sodium(208538-73-2)

Safety Data

• Hazardous Substances Data: 208538-73-2(Hazardous Substances Data)

Usage

Description

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.

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 208538-73-2 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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]

Brand name

Mycamine(Astellas).

Synthesis

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.

InChI:InChI=1/C56H71N9O23S.Na/c1-4-5-6-17-86-32-14-11-28(12-15-32)39-21-33(63-87-39)27-7-9-29(10-8-27)49(75)58-34-20-38(70)52(78)62-54(80)45-46(72)25(2)23-65(45)56(82)43(37(69)22-41(57)71)60-53(79)44(48(74)47(73)30-13-16-36(68)40(18-30)88-89(83,84)85)61-51(77)35-19-31(67)24-64(35)55(81)42(26(3)66)59-50(34)76;/h7-16,18,21,25-26,31,34-35,37-38,42-48,52,66-70,72-74,78H,4-6,17,19-20,22-24H2,1-3H3,(H2,57,71)(H,58,75)(H,59,76)(H,60,79)(H,61,77)(H,62,80)(H,83,84,85);/q;+1/p-1/t25-,26-,31+,34?,35-,37+,38+,42-,43-,44-,45-,46-,47+,48?,52-;/m1./s1