Anidulafungin
[CAS# 166663-25-8]

Identification

• Classification: API >> Special medicine >> Ophthalmic medication
• Name: Anidulafungin
• Synonyms: N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-4-[4-(4-pentoxyphenyl)phenyl]benzamide
• Molecular Formula: C₅₈H₇₃N₇O₁₇
• Molecular Weight: 1140.24
• CAS Registry Number: 166663-25-8
• EC Number: 658-060-4
• SMILES: CCCCCOC1=CC=C(C=C1)C2=CC=C(C=C2)C3=CC=C(C=C3)C(=O)N[C@H]4C[C@H]([C@H](NC(=O)[C@@H]5[C@H]([C@H](CN5C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]6C[C@H](CN6C(=O)[C@@H](NC4=O)[C@@H](C)O)O)[C@@H]([C@H](C7=CC=C(C=C7)O)O)O)[C@@H](C)O)C)O)O)O

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.688, Calc.^*
• Boiling Point: 1477.0±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 847.0±34.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07:GHS08 Warning
• Risk Statements: H302-H319-H361
• Safety Statements: P203-P264-P264+P265-P270-P280-P301+P317-P305+P351+P338-P318-P330-P337+P317-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400

Discovery and Applications

Anidulafungin, a member of the echinocandin class of antifungal agents, was discovered through the collaborative efforts of researchers at Eli Lilly and Company and Vicuron Pharmaceuticals in the late 1990s. The discovery process involved screening various chemical compounds for their antifungal activity, leading to the identification of anidulafungin as a promising candidate.

Anidulafungin is primarily used for the treatment of invasive candidiasis, a serious fungal infection caused by Candida species. It exerts its antifungal activity by inhibiting the synthesis of beta-(1,3)-D-glucan, a critical component of the fungal cell wall. This disrupts the integrity of the cell wall, leading to osmotic instability and ultimately fungal cell death. Anidulafungin is effective against a wide range of Candida species, including fluconazole-resistant strains, making it a valuable option in the management of invasive candidiasis. Anidulafungin is also indicated for the treatment of esophageal candidiasis, a fungal infection of the esophagus commonly seen in immunocompromised patients. Its efficacy in this setting has been demonstrated in clinical trials, with high rates of clinical and mycological response observed following treatment with anidulafungin. In addition to therapeutic use, anidulafungin is employed for prophylaxis in high-risk patients undergoing hematopoietic stem cell transplantation or other immunosuppressive therapies. Prophylactic administration of anidulafungin has been shown to reduce the incidence of invasive fungal infections, including candidiasis, in these vulnerable patient populations. Anidulafungin is often used as empirical therapy in patients with febrile neutropenia who are at high risk for invasive fungal infections. Its broad spectrum of activity against Candida species, combined with its favorable safety profile, makes it an attractive option for empiric antifungal therapy in this population.

References

2019. Lethal thrombosis of the iliac artery caused by Aspergillus fumigatus after liver transplantation: case report and review of the literature. BMC Surgery.
DOI: 10.1186/s12893-019-0668-4

2010. In Vivo Efficacy of Anidulafungin against Mature Candida albicans Biofilms in a Novel Rat Model of Catheter-Associated Candidiasis. Antimicrobial Agents and Chemotherapy.
DOI: 10.1128/aac.00697-10

2019. Spontaneous Mutational Frequency and FKS Mutation Rates Vary by Echinocandin Agent against Candida glabrata. Antimicrobial Agents and Chemotherapy.
DOI: 10.1128/aac.01692-18