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    Ciclopirox (HOE 296)
    Ciclopirox (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 #: V0186
    CAS #: 29342-05-0 Purity ≥98%

    Description: Ciclopirox (HOE-296; LACQUER; Penlac), a hydroxypyrimidine analog, is an potent, synthetic and broad-spectrum antifungal agent used for topical dermatologic treatment of superficial mycoses. It acts as an iron chelator and also inhibits the membrane transfer system by interrupting the Na+ K+ ATPase. Ciclopirox is currently being investigated as an alternative treatment to ketoconazole for seborrhoeic dermatitis.

    References: FASEB J. 2003 Apr;17(6):761-3; Br J Pharmacol. 2005 Jun;145(4):469-76.

    Related CAS: 41621-49-2 (Ciclopirox ethanolamine/olamine)

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    Molecular Weight (MW)207.27
    FormulaC12H17NO2
    CAS No.29342-05-0
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 42 mg/mL (202.6 mM)
    Water:  <1 mg/mL 
    Ethanol: 42 mg/mL (202.6 mM)
    Other info
    Chemical Name: 6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one
    InChi Key: SCKYRAXSEDYPSA-UHFFFAOYSA-N
    InChi Code: InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3
    SMILES Code: CC1=CC(=O)N(C(=C1)C2CCCCC2)O 
    SynonymsCiclopirox; Penlac; Batrafen; Ciclopiroxum; Loprox; HOE 296; HOE296; HOE-296; Ciclopirox olamine 


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    In Vitro

    In vitro activity: Ciclopirox olamine (CPX) is a lipophilic bidentate iron chelator that stabilizes HIF-1alpha under normoxic conditions at lower concentrations than other iron chelators, probably by inhibiting HIF-1alpha hydroxylation. Ciclopirox olamine (CPX)-induced HIF-1 mediates reporter gene activity and endogenous HIF-1 target gene expression, including elevation of transcription, mRNA, and protein levels of the vascular endothelial growth factor (VEGF). Ciclopirox inhibits growth of C. albicans yeast and hyphal cells in a dose-dependent manner. Ciclopirox blocks H2O2-induced mitochondrial injury by maintaining mitochondrial transmembrane potential (Deltapsim). Ciclopirox completely blocks H2O2-stimulated release of lactate dehydrogenase (a marker of cell death) and decreases in MTT reduction (a marker of mitochondrial function) in adenocarcinoma SK-HEP-1 cells. Ciclopirox effectively inhibits H2O2-induced mitochondrial permeability transition pore (MPTP) opening. Ciclopirox increases the MTP, maintained it high, and blocks the ATP depletion in glucose-deprived SIN-1-treated astrocytes. Ciclopirox protects astrocytes from peroxynitritecytotoxicity by attenuating peroxynitrite-induced mitochondrial dysfunction. Ciclopirox is a substituted pyridone antimycotic drug, unrelated to the imidazole derivatives and its topical application ensures maximum local bioavailability. Ciclopirox acts on fungi by inhibiting the intracellular uptake of essential substrates and ions and this probably acts on the Candida ability to express its adherence mechanisms.


    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. 
    Animal modelDifferent animal organ models including mouse skin wound model, rat kidney model and chicken chorioallantoic membrane model
    Formulation & DosageN/A
    ReferencesFASEB J. 2003 Apr;17(6):761-3; Br J Pharmacol. 2005 Jun;145(4):469-76; Antimicrob 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

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

    Ciclopirox

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


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