Anidulafungin

Base Information

• Chemical Name: Anidulafungin
• CAS No.: 166663-25-8
• Molecular Formula: C58H73N7O17
• Molecular Weight: 1140.25
• Mol file: 166663-25-8.mol

Synonyms:LY 303366;Ecalta;Eraxis;Anidulafungin;

Chemical Property of Anidulafungin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.688
• Boiling Point: 1477 °C at 760 mmHg
• PKA: 9.86±0.26(Predicted)
• Flash Point: 847 °C
• PSA: 377.42000
• Density: 1.47 g/cm³
• LogP: 0.65480
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)

Purity/Quality:

99%+ ^*data from raw suppliers

Anidulafungin-d11 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Anidulafungin, a semi-synthetic derivative of echinocandin B, has been developed and launched as an intravenous treatment for serious fungal infections, such as candidemia, Candida-derived peritonitis, intra-abdominal abscesses, and esophageal candidiasis. As a non-competitive inhibitor of 1,3-b-D-glucan synthase, which is responsible for the formation of glucan polymers, anidulafungin interferes with the cell wall synthesis of most pathogenic fungi. This mode of action is characteristic of the echinocandin class of antifungals. While the first member of this class, cilofungin, was withdrawn due to toxicity associated with the formulation vehicle, anidulafungin follows the successful introduction of caspofungin and micafungin. Compared to the other echinocandins, anidulafungin appears to be more potent (MIC90 ofr0.25 mg/mL for C.albicans, 0.5 mg/mL for C.glabrata, 1 mg/mL for C. krusel and C.tropicalis, 2mg/mL for C.lusitaniae, and 2 mg/mL for Aspergillus spp) and is devoid of significant drug interactions since it is neither an inhibitor nor substrate of the cytochrome P450 isoenzymes. The emergence of the echinocandins circumvents the concern regarding the rising resistance to the azole and amphotericin B antifungals; no cross-resistance is expected because the echinocandins work at the cell wall rather than the cell membrane.
• Uses: Anidulafungin is a semi-synthetic cyclic lipopeptide belonging to the echinocandin class that was reported in 1995 and commercially developed by Eli Lilly. Anidulafungin 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 400 citations. nucleoside reverse transcriptase inhibitor (NRTI) for HIV treatment in adults
• Clinical Use: Candidemia and certain invasive forms of candidosis Esophageal candidosis
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Anidulafungin

There total 6 articles about Anidulafungin 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: 71.0%

ECBN*HCl (1029890-89-8) + 1-({[4′′-(pentyloxy)-1,1′:4′,1′′-terphenyl-4-yl]carbonyl}oxy)-1H-1,2,3-benzotriazole → C82H95N7O19 + C58H73N7O17 + Anidulafungin (166663-25-8)

Guidance literature:

With potassium dihydrogenphosphate; In water; acetone; at 55 ℃; for 3h; Large scale;

DOI:10.1021/op800055h

Reference yield:

methyl 4-iodobenzoate (619-44-3) → Anidulafungin (166663-25-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) sec-butyllithium, 2.) triisopropyl borate, 3.) K₂CO₃, tetrakis(triphenylphosphine)palladium⁽⁰⁾

2: 2 N aq. NaOH / dioxane / 17 h / Heating

3: dicyclohexylcarbodiimide / CH₂Cl₂ / Ambient temperature

4: dimethylformamide / Ambient temperature

With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Triisopropyl borate; sec.-butyllithium; potassium carbonate; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00017a012

Reference yield:

4-bromo-4'-pentyloxybiphenyl (63619-51-2) → Anidulafungin (166663-25-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) sec-butyllithium, 2.) triisopropyl borate, 3.) K₂CO₃, tetrakis(triphenylphosphine)palladium⁽⁰⁾

2: 2 N aq. NaOH / dioxane / 17 h / Heating

3: dicyclohexylcarbodiimide / CH₂Cl₂ / Ambient temperature

4: dimethylformamide / Ambient temperature

With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Triisopropyl borate; sec.-butyllithium; potassium carbonate; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00017a012

upstream raw materials:

2,4,5-trichlorophenyl 4-(4'-pentyloxybiphenyl)benzoate

echinocandin B

methyl 4-iodobenzoate

4-bromo-4'-pentyloxybiphenyl

Downstream raw materials:

4''-pentyloxy-[1,1';4',1'']terphenyl-4-carboxylic acid {11,20,25-trihydroxy-3,15-bis-(1-hydroxy-ethyl)-6-[1-hydroxy-2-(4-hydroxy-phenyl)-ethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaaza-tricyclo[22.3.0.0^9,13]heptacos-18-yl}-amide

C₆₃H₈₅N₇O₁₇Si

Refernces

• 1、 Debono, Manuel,Turner, William W.,LaGrandeur, Lisa,Burkhadt, Fred J.,Nissen , Jeffrey S.,et al.. "Semisynthetic Chemical Modification of the Antifungal Lipopeptide Echinocandin B (ECB): Structure-Activity Studies of the Lipophilic and Geometric Parameters of Polyarylated Acyl Analogs of ECB". . p. 3271 - 3281. Retrieved 2007/10/02.