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

Micafungin sodium is a semi-synthetic echinocandin antifungal agent, which is a 1,3-β-glucan synthase inhibitor. It is the sodium salt of the semi-synthetic cyclic lipopeptide, micafungin, a member of the echinocandin class. Micafungin sodium was discovered by Fujisawa in Japan and is known for its improved water solubility due to the aryl sulphate moiety, making it the preferred salt for pharmaceutical applications. It is used for the treatment and prevention of infections caused by Aspergillus and Candida, such as fungemia, respiratory mycosis, and gastrointestinal mycosis.

Uses

Used in Pharmaceutical Industry:
Micafungin sodium is used as an antifungal agent for the treatment and prevention of infections caused by Aspergillus and Candida species. It inhibits the synthesis of 1,3-β-D-glucan, an essential component of the fungal cell wall, making it a valuable treatment option for fungal infections.
Used in Antifungal Treatments:
Micafungin sodium is used as a fungicidal agent against virtually all species of Candida, including those resistant to fluconazole, and as a fungistatic agent against Aspergillus spp. This makes it an important component in the arsenal against drug-resistant fungal infections.
Chemical Properties:
Micafungin sodium is an off-white solid with improved water solubility due to its sodium salt form.
Brand Name:
The brand name for micafungin sodium is Mycamine, which is manufactured by 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