Ciclopirox ethanolamine

• CAT Number: A000713
• CAS Number: 41621-49-2
• Molecular Formula: C12H17NO2.C2H7NO
• Molecular Weight: 268.35
• Purity: ≥95%
• Synonyms: Ciclopirox ethanolamine; ciclopiroxolamine; Ciclobirox Olamine
• Target: ATPase
• Solubility: Soluble in DMSO > 10 mM
• Storage: 3 years -20C powder
• IUPAC Name: 2-aminoethanol;6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one
• InChI: InChI=1S/C12H17NO2.C2H7NO/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10;3-1-2-4/h7-8,10,15H,2-6H2,1H3;4H,1-3H2
• InChIKey: MBRHNTMUYWQHMR-UHFFFAOYSA-N
• SMILES: CC1=CC(=O)N(C(=C1)C2CCCCC2)O.C(CO)N

Ciclopirox ethanolamine (Ciclopirox olamine, HOE 296) (CAS 41621-49-2) is a broad-spectrum antifungal agent working as an iron chelator.
Ciclopirox significantly inhibits the growth of C. albicans strain SC5314 cells, with MIC80s of 1.0-2.0 μg/mL, growth decreased dramatically at the concentrations of >0.6 μg/mL, and almost complete growth inhibition at concentration of 0.7 μg/mL, unlike fluconazole which shows a much wider range of concentrations with intermediate inhibition. Like iron chelator bipyridine, Ciclopirox reduces cell growth by binding to iron ions, which can be reversed by addition of FeCl3. Moreover, Ciclopirox treatment at subinhibitory concentration (0.6 μg/mL) only moderately reduces the virulence genes such as genes encoding secreted proteinases or lipases, but leads to a distinct up- or down-regulation of genes encoding iron permeases or transporters (FTR1, FTR2, and FTH1), a copper permease (CCC2), an iron reductase (CFL1), and a siderophore transporter (SIT1). Although the Candida drug resistance genes CDR1 and CDR2 are up-regulated after Ciclopirox treatment, no change in resistance or increased tolerance could be observed even after an incubation period of 6 months, in contrast to fluconazole in which the MICs for cells noticeably increase after 2 months.

Reference

1.Sigle, Hans-Christian, et al. "Oxygen accessibility and iron levels are critical factors for the antifungal action of ciclopirox against Candida albicans." Journal of Antimicrobial Chemotherapy 55.5 (2005): 663-673.