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Some antifungal drugs that inhibit the synthesis of β- (1, 3) - D-glucan

 

1.     Caspofungin Acetate CAS No.:179463-17-3

Caspofungin is a semisynthetic echinocandin antifungal agent,it is mainly used in treating that candidiasis esophagitis or oropharynx are scorching, invasive aspergillosis.

1) Fermentation: The natural lipophilic cyclic peptide precursor, Pneumocandin B0 (CAS No.: 135575-42-7), is produced via large-scale fungal cultivation of the fungus, Glarea lozoyensis. Pneumocandin C0 (CAS: 144074-96-4) is an isomer of Pneumocandin B0, need to be removed during separation and purification.

2) Chemical Semisynthesis:

Its manufacturing process primarily involves a two-step method:

 


2.     Micafungin Sodium CAS No.:208538-73-2

Micafungin sodium is a semisynthetic echinocandin antifungal agent,it is approved for treatment esophagus The prophylactic treatment of monilial infection, bone-marrow transplantation and ADS patient's neutrophilic granulocytopenia.

Its manufacturing process primarily involves a three-step method:

1)      Fermentation: The natural cyclic hexapeptide precursor, FR901379 (CAS No.: 144371-88-0), is produced via large-scale fungal cultivation of the fungus, Coleophoma empetri

2)      Enzymatic Deacylation: The precursor is enzymatically deacylated to remove the naturally occurring fatty acid side chain, yielding a core nucleus FR179642 (CAS No.: 168110-44-9). 

3)      Chemical Reacylation: The core nucleus is then chemically reacylated using an optimized, synthetically derived N-acyl side chain (the 3,5-diphenyl-substituted isoxazole ring), yielding micafungin. The distinct sulfonate group present in micafungin provides its high water solubility, differentiating it from other echinocandins.


 3.      Anidulafungin CAS No.: 166663-25-8

Anidulafungin is a semisynthetic echinocandin antifungal agent,it is approved for treatment Treatment of candidemia and other types of Candida infections, as well as esophageal candidiasis.

Its manufacturing process primarily involves a three-step method:

4)      Fermentation: The natural cyclic hexapeptide precursor, Echinocandin B (ECB) (CAS: 54651-05-7), is produced via large-scale fungal cultivation of the fungus, Aspergillus nidulans

5)      Enzymatic Deacylation: The precursor is enzymatically deacylated to remove the naturally occurring fatty acid side chain, obtaining Echinocandin B Nucleus (ECBN) (Echinocandin B0 Hydrochloride CAS 1029890-89-8). 

6)      Chemical Reacylation: The core nucleus is then chemically chemically modified and added with the side chain pentoxytriphenylcarboxyl group to obtain Anidulafungin.

4.     Rezafungin Acetate CAS No.: 1396640-59-7

Rezafungin is a semisynthetic echinocandin antifungal agent, it is mainly used for treating invasive candidiasis in adults. Rezafungin can be further processed from Echinocandin B Nucleus (ECBN) (Echinocandin B0 Hydrochloride CAS 1029890-89-8).

5.     Cilofungin CAS No.:79404-91-4

Rezafungin is a semisynthetic echinocandin antifungal agent,it can be further processed from Echinocandin B Nucleus (ECBN) (Echinocandin B0 Hydrochloride CAS 1029890-89-8).


6.     Enfumafungin CAS NO.: 260979-95-1

Enfumafungin is a hemiacetal triterpene glycoside that is produced in fermentations of a Hormonema carpetanum associated with living leaves of Juniperus communis. It is an inhibitor of (1, 3) - β -D-glucan synthesis, and is useful in the treatment of systemic fungal infections.

Enfumafungin structure is as following:

7.     Ibrexafungerp Citrate  CAS NO.:1965291-08-0

Ibrexafungerp, developed with enfumafungin as a precursor, has obtained clinical drug approval from the US FDA for oral treatment of acute and recurrent vulvovaginal candidiasis.

Ibrexafungerp is mainly obtained by fermenting enfumafungin with the strain Hormonema carpetanum, then hydrolyzing it into aglycone, and then chemically modified.