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    Ciclopirox ethanolamine (HOE 296)
    Ciclopirox ethanolamine (HOE 296)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1681
    CAS #: 41621-49-2 Purity ≥98%

    Description: Ciclopirox ethanolamine (also known as Ciclopirox olamine, HOE 296) is a novel, investigational, synthetic, potent and broad-spectrum antifungal agent working as an iron chelator and used as an antifungal agent for topical dermatologic treatment of superficial mycoses. It is currently being investigated as an alternative treatment to ketoconazole for seborrhoeic dermatitis as it suppresses growth of the yeast Malassezia furfur.It acts by inhibiting the membrane transfer system by interrupting the Na+ K+ ATPase. Ciclopirox ethanolamine suppresses many clinically relevant dermatophytes, yeasts, and molds, including the frequently azole-resistant Candida species Candida glabrata, and Candida guilliermondii. Moreover, Ciclopirox has been proved to inhibit a wide range of bacteria in humans, including many gram(+) and gram (-) species pathogenic bacteria.

    References: Antimicrob Agents Chemother. 2003 Jun;47(6):1805-17; Antimicrob Agents Chemother. 2009 Jun;53(6):2654-6.

    Related CAS #29342-05-0 (Ciclopirox free); 30652-11-0 (Deferiprone)

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    Molecular Weight (MW)268.35
    FormulaC12H17NO2.C2H7NO 
    CAS No.41621-49-2(Ciclopirox ethanolamine/olamine); 
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 6 mg/mL (22.4 mM)
    Water: <1 mg/mL 
    Ethanol: 30 mg/mL (111.8 mM)
    Other info
    Chemical Name: 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone Ethanolamine Salt
    InChi Key: HKUKJIQHPXYJTP-UHFFFAOYSA-O
    InChi Code: InChI=1S/C12H16NO2.C2H7NO/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10;3-1-2-4/h7-8,10H,2-6H2,1H3;4H,1-3H2/q-1;/p+1
    SMILES Code: [NH3+]CCO.O=C1C=C(C)C=C(C2CCCCC2)N1[O-] 
    SynonymsCiclopirox olamine; Ciclopirox ethanolamine


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    In Vitro

    In vitro activity: 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. Ciclopirox inhibits the growth of Aspergillus fumigatus strain B5233 with IC50 of 4.22 μM, more potently compared with deferiprone with IC50 of 1.29 mM.


    Cell Assay: Sabouraud glucose medium (2%) is used for cell culture growth, and RPMI 2% glucose medium and 2% Sabouraud glucose medium are used for MIC determinations. For cell culture growth curves, 220 mL of 2% Sabouraud glucose medium containing different concentrations of Ciclopirox are inoculated with 105 cells/mL, and the mixture is shaken at 160 rpm and 37 °C for 1-10 hours. Growth is measured photometrically at 630 nm. FeCl3 or 2,2'-bipyridine is added to the medium at different concentrations for inhibition studie.

    In VivoThe effect of Ciclopirox on endogenous HIF-1 target gene-VEGF was investigated using different animal organ models including mouse skin wound model, rat kidney model and chicken chorioallantoic membrane model. According to the results, CPX functionally activated HIF-1, induced VEGF expression and accelerated angiogenesis. 
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    ReferencesAntimicrob Agents Chemother. 2003 Jun;47(6):1805-17; Antimicrob Agents Chemother. 2009 Jun;53(6):2654-6.


    These protocols are for reference only. InvivoChem does not independently validate these methods.

    Ciclopirox ethanolamine

    CPX inhibits H2O2-induced mitochondrial swelling in isolated mitochondria. Br J Pharmacol. 2005 Jun;145(4):469-76.

    Ciclopirox ethanolamine

    CPX prevents H2O2-stimulated Δψm depolarization in cells. Br J Pharmacol. 2005 Jun;145(4):469-76.
     

    Ciclopirox ethanolamine

    CPX prevents H2O2-stimulated Δψm depolarization in cells. Br J Pharmacol. 2005 Jun;145(4):469-76.


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