1-[(4R,5R)-4,5-Dihydroxy-L-ornithine]echinocandin B hydrochloride (1:1)
[CAS# 1029890-89-8]

Identification

• Classification: API >> Synthetic anti-infective drugs >> Antifungal drugs
• Name: 1-[(4R,5R)-4,5-Dihydroxy-L-ornithine]echinocandin B hydrochloride (1:1)
• Synonyms: (3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-18-amino-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0?,¹³]heptacosane-2,5,8,14,17,23-hexone hydrochlo
• Molecular Formula: C₃₄H₅₁N₇O₁₅.HCl
• Molecular Weight: 834.27
• CAS Registry Number: 1029890-89-8
• SMILES: C[C@H]1CN2[C@@H]([C@H]1O)C(=O)N[C@@H]([C@@H](C[C@@H](C(=O)N[C@H](C(=O)N3C[C@@H](C[C@H]3C(=O)N[C@H](C(=O)N[C@H](C2=O)[C@@H](C)O)[C@@H]([C@H](C4=CC=C(C=C4)O)O)O)O)[C@@H](C)O)N)O)O.Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

1-[(4R,5R)-4,5-Dihydroxy-L-ornithine]echinocandin B hydrochloride, commonly known as echinocandin B, was discovered in the 1960s as a natural product of fungal fermentation. It is produced by various fungal species, including Aspergillus nidulans and Aspergillus rugulosus. Echinocandin B belongs to the echinocandin class of antifungal compounds, which inhibit the synthesis of ß(1,3)-D-glucan, an essential component of the fungal cell wall. Echinocandin B and its derivatives have significant applications in medicine, particularly in the treatment of invasive fungal infections.

Echinocandin B exhibits potent antifungal activity against a broad spectrum of clinically important fungi, including Candida and Aspergillus species. Its mechanism of action involves inhibiting the enzyme ß(1,3)-D-glucan synthase, which disrupts the synthesis of fungal cell walls, leading to cell lysis and death. This mechanism makes echinocandin B highly effective against fungal pathogens while minimizing toxicity to mammalian cells. Echinocandin B and its derivatives are primarily used for the treatment of invasive fungal infections, including candidemia, invasive candidiasis, and invasive aspergillosis. These infections often occur in immunocompromised patients, such as those undergoing chemotherapy or organ transplantation, where they pose significant morbidity and mortality risks. While echinocandin B itself is not commonly used in clinical practice due to its poor solubility and pharmacokinetic properties, its discovery paved the way for the development of semisynthetic derivatives with improved drug-like properties. Caspofungin, micafungin, and anidulafungin are examples of echinocandin derivatives that have been developed for clinical use. These derivatives retain the potent antifungal activity of echinocandin B while addressing issues such as solubility and stability, thereby enhancing their clinical utility.

References

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