Caspofungine

Base Information

• Chemical Name: Caspofungine
• CAS No.: 179463-17-3
• Molecular Formula: 2C₂H₄O₂*C₅₂H₈₈N₁₀O₁₅
• Molecular Weight: 1213.43
• Hs Code.: 2933990090
• Wikipedia: Caspofungin
• NCI Thesaurus Code: C28910
• RXCUI: 140108
• Metabolomics Workbench ID: 42861
• Mol file: 179463-17-3.mol

Synonyms:Cancidas;caspofungin;caspofungin acetate;Caspofungin MSD;L 743,872;L 743872;L-743,872;L-743872;L743,872;L743872;MK 0991;MK-0991;MK0991

Chemical Property of Caspofungine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1501.4 °C at 760 mmHg
• Flash Point: 861.8 °C
• PSA: 412.03000
• LogP: 0.06150
• Storage Temp.: ?20°C
• Solubility.: H2O: soluble15mg/mL (clear solution)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 16
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 23
• Exact Mass: 1092.64306214
• Heavy Atom Count: 77
• Complexity: 1900

Purity/Quality:

99% ,99.9%, ^*data from raw suppliers

CaspofunginAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)CC(C)CCCCCCCCC(=O)NC1CC(C(NC(=O)C2C(CCN2C(=O)C(NC(=O)C(NC(=O)C3CC(CN3C(=O)C(NC1=O)C(C)O)O)C(C(C4=CC=C(C=C4)O)O)O)C(CCN)O)O)NCCN)O
• Isomeric SMILES: CCC(C)CC(C)CCCCCCCCC(=O)NC1C[C@H]([C@H](NC(=O)[C@@H]2[C@H](CCN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@@H](NC1=O)[C@@H](C)O)O)[C@@H]([C@H](C4=CC=C(C=C4)O)O)O)[C@@H](CCN)O)O)NCCN)O
• Recent ClinicalTrials: A Study to Learn About the Study Medicine (Called Fosmanogepix/ PF-07842805) in People With Candidemia and/or Invasive Candidiasis.
• Recent EU Clinical Trials: A Phase 3, Multicenter, Prospective, Randomized, Double-blind Study of Two Treatment Regimens for Candidemia and/or Invasive Candidiasis: Intravenous Echinocandin followed by Oral Ibrexafungerp versus Intravenous Echinocandin followed by Oral Fluconazole (MARIO)
• Description: Caspofungin is the first in a new class of antifungal agents named echinocandin to be launched in the US for the parenteral treatment of invasive aspergillosis in patients refractory to, or intolerant of other antifungal therapies such as amphotericin-B1 lipid formulation of amphotericin-B and/or itraconazole. Caspofungin is a water soluble, stable, aza-substituted semisynthetic derivative of pneumocandin B, a fermentation product of the fungus Zalerion arboricola. Since fungi and humans are both eukaryotes, new antifungal agents must focus on fungus-specific targets in order to minimize potential toxicity in the human host. In this respect, the lipopeptide caspofungin, inhibits the synthesis of 1,3-beta- D-glucans present only in the fungal cell wall, which leads to the specific lysis of the pathogenic cells. The compound is fungicidal rather than fungistatic, an unusual feature among antifungal agents. Caspofungin has activity in vitro and in vivo against a range of Candida species (including azole and amphotericin B resistant Candida) and also against Aspergillus, an important pathogen which is not susceptible to fluconazole. Caspofungin was generally more active than amphotericin B, flucytosine, fluconazole and itraconazole against Candida species. Cryptococcus is not susceptible to caspofungin. Caspofungin has a half-life in human beings around 10 hours. Unlike the azoles, caspofungin does not inhibit cytochrome P450. The drug has been given intravenously with loading dose of 70 rag, followed by 50 mg daily to be effective in invasive aspergillosis refractory to prior antifungal therapy. Most of the side effects were mild and comprised fever, thrombophlebitis, headache, nausea, rash and flushing. Caspofungin is an antifungal compound that is classified as an echinocandin, as it acts by noncompetititvely inhibiting the enzyme 1,3-β glucan synthase and preventing the synthesis of glucan in the fungal cell wall. It is effective against disseminated or invasive aspergillosis and candidiasis in mice. Caspofungin has a 50% minimum effective concentration against Aspergillus spp. of 0.015 μg/ml. It does not antagonize other antifungal compounds, like amphotericin B, and, in some cases, may show additive or synergistic activity.
• Uses: An echinocandin that inhibits the synthesis of β (1,3)-D-glucan, an integral component of the fungal cell wall. An antifungal drug used in the treatment of invasive fungal infections. Caspofungin acetate is a semi-synthetic analogue of pneumocandin B0 with improved water solubility, a significant limitation in the development of the echinocandin class as pharmaceuticals. Caspofungin acetate acts by inhibiting the synthesis of β-(1,3)-D-glucan, an essential component of the cell wall of susceptible fungi. Calcium antagonist, coronary vasodilator, anti-inflammatory, analgesic Caspofungin Diacetate is an impurity of Caspofungin Acetate(C184900) which is an echinocandin that inhibits the synthesis of β (1,3)-D-glucan, an integral component of the fungal cell wall. An antifungal drug used in the treatment of invasive fungal infections.

Technology Process of Caspofungine

There total 36 articles about Caspofungine 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: 85.0%

C56H86N8O15S*ClH + acetic acid (64-19-7,77671-22-8) + ethylenediamine (107-15-3,85404-18-8) → C52H88N10O15*2C2H4O2 (179463-17-3) + caspofungin bis(acetic acid) salt (179463-17-3)

Guidance literature:

C₅₆H₈₆N₈O₁₅S*ClH; ethylenediamine; In methanol; at 25 ℃; for 24h;

acetic acid; In methanol; water; pH=5.0 - 5.5;

DOI:10.1021/jo062008i

Reference yield: 85.0%

C56H86N8O15S*ClH + acetic acid (64-19-7,77671-22-8) + ethylenediamine (107-15-3,85404-18-8) → C52H88N10O15*2C2H4O2 (179463-17-3) + caspofungin bis(acetic acid) salt (179463-17-3)

Guidance literature:

C₅₆H₈₆N₈O₁₅S*ClH; ethylenediamine; In methanol; at 25 ℃; for 24h;

acetic acid; In methanol; water; pH=5.0 - 5.5;

DOI:10.1021/jo062008i

Reference yield: 81.2%

C53H86N8O17S + acetic acid (64-19-7,77671-22-8) + ethylenediamine (107-15-3,85404-18-8) → caspofungin diacetate (179463-17-3)

Guidance literature:

C₅₃H₈₆N₈O₁₇S; ethylenediamine; at 20 ℃; for 2h;

acetic acid; In methanol; water; at 20 ℃;

upstream raw materials:

acetic acid

ethylenediamine

pneumocandin B₀

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF CASPOFUNGIN ACETATE AND INTERMEDIATES". Page/Page column. . Retrieved 2014/02/15.
• 2、 -. "Process for preparation of Caspofungin acetate". Page/Page column 5. . Retrieved 2010/07/08.