Ciclopirox ethanolamine [41621-49-2]

Biological Activity

Ciclopirox ethanolamine is a broad-spectrum antifungal agent working as an iron chelator. Ciclopirox inhibits nearly all clinically relevant dermatophytes, yeasts, and molds, including the frequently azole-resistant Candida species Candida glabrata, Candida krusei, and Candida guilliermondii. In addition, Ciclopirox acts against a wide range of bacteria including many gram-positive and gram-negative species pathogenic for humans. Ciclopirox inhibits dermatophytes and yeasts pathogenic with MICs of 0.98-3.9 μg/mL. Ciclopirox can be rapidly taken up by growing C. albicans cells, and intracellular accumulation of Ciclopirox can lead to levels 200 times greater than those in the medium. More than 97% of the accumulated Ciclopirox is bound largely irreversibly to different cell structures and organelles such as the cell membrane, cell wall, mitochondria, microsomes, and ribosomes, while only small amounts are found in the cytosolic fraction. Moreover, Ciclopirox is neither metabolized nor degraded. In addition, Ciclopirox at higher concentrations leads to cellular leakage, causing the loss of folin-positive substances and potassium ions from the cell without affecting the fungal cell wall. Ciclopirox inhibits the synthesis of protein, RNA, and DNA in growing fungal cells, possibly by blocking the uptake of precursors of the macromolecules or by blocking the uptake of essential ions such as potassium ions and phosphates. Similar to rilopirox, Ciclopirox at subinhibitory concentration causes modifications in particle distribution within the plasma membrane, having an effect on the adherence of C. albicans to buccal and vaginal epithelial cells. The chelation of metal ions and the inhibition of iron-dependent enzymes play a primary role in the action of Ciclopirox.Ciclopirox alone potently inhibits the growth of Aspergillus fumigatus B5233 conidia, and Ciclopirox in combination with ketoconazole displays synergistic antifungal activity.

Product Citations

• 

  J Hazard Mater. 2024 Jul 15;476:135211.

  Neurodevelopmental toxicity of a ubiquitous disinfection by-product, bromoacetic acid, in Zebrafish (Danio rerio)
  Ciclopirox ethanolamine purchased from AbMole

Protocol (for reference only)

Cell Experiment
Cell lines	C. albicans strain SC5314
Preparation method	Using sabouraud glucose medium (2%) for cell culture growth, and RPMI 2% glucose medium and 2% Sabouraud glucose medium are used for MIC determinations. For cell culture growth curves, inoculating 220 mL of 2% Sabouraud glucose medium which contains different concentrations of Ciclopirox with 105 cells/mL, and shaking the mixture at 160 rpm and 37 °C for 1-10 hours. Measuring growth photometrically at 630 nm. Adding feCl3 or 2,2'-bipyridine to the medium at different concentrations for inhibition studie
Concentrations	Dissolved in DMSO, final concentrations 10 μg/mL
Incubation time	1-10 hours

Animal Experiment
Animal models
Formulation
Dosages
Administration

Chemical Information

Molecular Weight	268.35
Formula	C12H17NO2.C2H7NO
CAS Number	41621-49-2
Solubility (25°C)	Ethanol 30 mg/mL DMSO 20 mg/mL
Storage	2-8°C, dry, sealed

References

[1] Alex Farr, et al. Guideline: Vulvovaginal candidosis (AWMF 015/072, level S2k)

[2] Jose W Ricardo, et al. Safety of current therapies for onychomycosis

[3] Bianca Maria Piraccini, et al. Ciclopirox Hydroxypropyl Chitosan (HPCH) Nail Lacquer: A Review of Its Use in Onychomycosis

[4] No authors listed. Ciclopirox

[5] Shari R Lipner, et al. Onychomycosis: Treatment and prevention of recurrence