Micafungin

Base Information

• Chemical Name: Micafungin
• CAS No.: 235114-32-6
• Molecular Formula: C₅₆H₇₁N₉O₂₃S
• Molecular Weight: 1270.29
• Mol file: 235114-32-6.mol

Synonyms:Mycamine;1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacycloheneicosine-20-propanamide, 23-[1,2-dihydroxy-2-[4-hydroxy-3-(sulfooxy)phenyl]ethyl]tetracosahydro-β,2,11,12,15-pentahydroxy-6-(1-hydroxyethyl)-16-methyl-5,8,14,19,22,25-hexaoxo-9-[[4-[5-[4-(pentyloxy)phenyl]-3-isoxazolyl]benzoyl]amino]-;

Chemical Property of Micafungin

Chemical Property:

• Refractive Index: 1.706
• PKA: -4.46±0.18(Predicted)
• PSA: 518.52000
• Density: 1.62 g/cm³
• LogP: -0.53900
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Heated)

Purity/Quality:

99%min ^*data from raw suppliers

Micafungin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Micafungin (trade name Mycamine) is a kind of echinocandin antifungal drug. Its mechanism of action is through inhibiting the synthesis of beta-1, 3-glucan, which is an essential component of fungal cell walls, but not presented in mammalian cells. It works through inhibiting the beta-1,3-D glucan synthase. It can be used for the treatment of candidemia, acute disseminated candidiasis, candida peritonitis, abscesses and esophageal candidiasis. It is fungicidal against some candida, but fungistatic against Apergillus. It is also used in combinations with many other drugs such as the HIV protease inhibitor ritonavir as well as the transplant medications cyclosporine and tacrolimus. Micafungin, the second member of the echinocandin class of antifungal agents was launched in Japan for the parenteral treatment of various fungal infections caused by Aspergillus and Candida spp. such as fungaemia and respiratory and gastrointestinal mycoses. This water-soluble semisynthetic cyclic lipopeptide is synthesized by acylation with (5-(4- pentyloxyphenyl)isoxazol-3-yl)benzoate of the cyclic peptide nucleus (FR-179642).obtained by enzymatic cleavage of the naturally occurring echinocandin FR-901379, derived from the fungus Coleophoma empedri Micafungin acts by inhibiting the synthesis of 1,3-beta-glucan, an essential polysaccharide of the cell wall of many pathogenic fungi. Micafungin has a marked fungicidal effect on almost all species of Candida, including fluconazole-resistant spp. C. albicans, C. glabrata, C. Krusei, C. parapsilosis and C. tropicalis and a fungistatic effect on a range of Aspergillus species including A. flaws, A. fumigates and A. terreus. Like caspofungin, micafungin is inactive against Cryptococcus neoformans, and the emerging pathogen Trichosporon cutaneum and Fusarium solani. Micafungin has proved highly effective in mouse models of Cancfidiasis and Aspergillus infections (including those using an amphotericin B- and itraconazole-resistant isolate of A. fumigatus). In phase I studies, micafungin had linear pharmacokinetics with an elimination half-life ranging from 11.7 to 15.2 h after injection and was well tolerated.
• Uses: Micafungin is an antifungal drug that inhibits the production of β-1,3-glucan, an essential component of fungal cell walls. Micafungin is a semi-synthetic cyclic lipopeptide belonging to the echinocandin class that was reported in 1999 from Fujisawa in Japan. Unlike other marketed semi-synthetic derivatives in this class, micafungin is not derived from echinocandin but rather from FR901379 which contains a phenolic sulphate to enhance aqueous solubility, a serious limitation in the class. Micafungin inhibits the synthesis of β-(1,3)-D-glucan, an essential component of the cell wall of susceptible fungi and is extensively referenced in the literature with over 700 citations.
• Clinical Use: Candidemia and certain invasive forms of candidosis Esophageal candidosis Prophylaxis of Candida infections in hematopoietic stem cell transplant (HSCT) recipients
• Drug interactions: Potentially hazardous interactions with other drugs Ciclosporin: possibly increases ciclosporin concentration. Sirolimus: increases sirolimus concentration.

Technology Process of Micafungin

There total 9 articles about Micafungin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

benzotriazol-1-ol (2592-95-2) + 4-{5-[4-(pentyloxy)phenyl]-1,2-oxazol-3-yl}benzoic acid (179162-55-1) → micafungin (235114-32-6)

Guidance literature:

benzotriazol-1-ol; 4-{5-[4-(pentyloxy)phenyl]-1,2-oxazol-3-yl}benzoic acid; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25 ℃; for 4h;

4-{5-[4-(pentyloxy)phenyl]-1,2-oxazol-3-yl}benzoic acid; With N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide; acetone; at 0 - 10 ℃; for 0.308333h;

Reference yield: 90.0%

C27H27N3O5 → micafungin (235114-32-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; at 0 - 10 ℃; for 2.5h;

Reference yield: 86.0%

FR-179642 + C27H24N4O3 → micafungin (235114-32-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In methanol; ethyl acetate; N,N-dimethyl-formamide; acetone; at 0 - 10 ℃; for 20h;

upstream raw materials:

FR 179642

1-[[4-[5-(4-pentyloxyphenyl)isoxazol-3-yl]benzoyl]oxy]-1H-1,2,3-benzotriazole

C₂₁H₂₀ClNO₃

C₂₇H₂₈N₃O₉P

Refernces

• 1、 -. "PREPARATION OF MICAFUNGIN INTERMEDIATES". Paragraph 0058. . Retrieved 2014/11/13.
• 2、 -. "PREPARATION OF MICAFUNGIN INTERMEDIATES". Page/Page column 40-41. . Retrieved 2013/03/26.