Micafungin sodium
[CAS# 208538-73-2]

Identification

• Classification: API >> Special medicine >> Ophthalmic medication
• Name: Micafungin sodium
• Synonyms: Mycamine; FK 463; sodium [5-[(1S,2S)-2-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-3-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-18-[[4-[5-(4-pentoxyphenyl)-1,2-oxazol-3-yl]benzoyl]amino]-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-6-yl]-1,2-dihydroxyethyl]-2-hydroxyphenyl] sulfate
• Molecular Formula: C₅₆H₇₀N₉O₂₃S.Na
• Molecular Weight: 1292.26
• CAS Registry Number: 208538-73-2
• EC Number: 810-840-7
• SMILES: CCCCCOC1=CC=C(C=C1)C2=CC(=NO2)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)OS(=O)(=O)[O-])O)O)[C@@H](CC(=O)N)O)C)O)O)O.[Na+]

Properties

• Solubility: 2 mg/mL (H2O)

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Dander
• Risk Statements: H302-H319-H332-H351-H361-H372-H373-H400-H410
• Safety Statements: P203-P260-P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P304+P340-P305+P351+P338-P317-P318-P319-P330-P337+P317-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	4	H302
Carcinogenicity	Carc.	2	H351
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Specific target organ toxicity - repeated exposure	STOT RE	1	H372

Discovery and Applications

Micafungin sodium is an antifungal medication used primarily for the treatment of serious fungal infections, particularly those caused by Candida species. It belongs to the echinocandin class of antifungals, which work by inhibiting the synthesis of glucan, a key component of the fungal cell wall. By disrupting the integrity of the cell wall, micafungin prevents fungal growth and reproduction. Micafungin is particularly effective against invasive fungal infections, including candidemia and esophageal candidiasis, and is often used in immunocompromised patients, such as those undergoing chemotherapy or organ transplantation.

The discovery of micafungin sodium traces back to the 1990s, when researchers at Astellas Pharma, in collaboration with scientists from other organizations, were working to develop new antifungal agents. The emergence of drug-resistant fungal pathogens, particularly species of Candida, highlighted the need for more potent and effective treatments. The echinocandin class, which includes micafungin, was identified as a promising alternative to older antifungal classes like azoles and polyenes. These new drugs offered a mechanism of action that was less likely to be affected by existing antifungal resistance, making them ideal candidates for the treatment of difficult-to-treat fungal infections.

Micafungin sodium is administered intravenously, typically in hospital settings due to its formulation and the need for careful monitoring. It is used to treat invasive candidiasis, including candidemia, and is also approved for the prevention of Candida infections in patients undergoing hematopoietic stem cell transplantation. Its broad-spectrum activity includes efficacy against not only Candida species but also Aspergillus species, making it a valuable option for patients with a variety of fungal infections.

One of the key advantages of micafungin sodium over other antifungal treatments is its favorable safety profile. While it may cause some side effects, including liver enzyme abnormalities and gastrointestinal issues, it is generally well-tolerated. Micafungin also has a low potential for drug interactions, which makes it a preferred option for patients receiving multiple medications. Unlike fluconazole and other azoles, which can have significant interactions with drugs that affect the liver enzyme CYP3A4, micafungin is not metabolized by this pathway, reducing the risk of drug-drug interactions.

Micafungin’s mode of action is unique compared to other antifungals. It targets the fungal cell wall, a structure not present in human cells, thus reducing the risk of toxicity to the host. The inhibition of glucan synthesis weakens the cell wall, leading to cell lysis and death. This mechanism makes micafungin particularly effective against certain resistant fungal pathogens that are not susceptible to other antifungal classes. Furthermore, echinocandins like micafungin do not have the nephrotoxic effects that can be seen with some other antifungal agents, such as amphotericin B.

Clinical studies have shown that micafungin is effective in both treating and preventing Candida infections, with favorable outcomes in terms of mortality rates and the resolution of infection. It has become a mainstay in the treatment of invasive candidiasis, particularly in critically ill patients who are at high risk for fungal infections. Micafungin is also being investigated for potential use in combination therapies, as combining it with other antifungal agents may increase its efficacy, particularly in the treatment of difficult-to-eradicate infections like those caused by Aspergillus.

In conclusion, micafungin sodium is an important antifungal drug with a well-established role in the treatment and prevention of serious fungal infections. Its efficacy against Candida and Aspergillus species, along with its favorable safety profile and unique mechanism of action, make it a valuable tool in the management of invasive fungal diseases, particularly in immunocompromised patients. As the prevalence of invasive fungal infections continues to rise, micafungin remains a critical component in the fight against these potentially life-threatening conditions.

References

2017. Infectious complications in multiple myeloma receiving autologous stem cell transplantation in the past 10 years. International Journal of Hematology, 106(2).
DOI: 10.1007/s12185-017-2313-2

2024. Fungal Fighters: A Comprehensive Guide to Antifungal Therapies of the Past, Present, and Future. Recent Advances in Human Fungal Diseases.
DOI: 10.1007/978-981-97-4909-6_2

2010. Efficacy and Safety of Micafungin as an Empirical Antifungal Agent for Febrile Neutropenic Patients with Hematological Diseases. Acta Haematologica, 124(2).
DOI: 10.1159/000315558