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Ciclopirox (HOE 296)

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Ciclopirox (HOE 296)
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Cat #: V0186 CAS #: 29342-05-0 Purity ≥ 99%

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: [1]. Niewerth, M., et al., Ciclopirox olamine treatment affects the expression pattern of Candida albicans genes encoding virulence factors, iron metabolism proteins, and drug resistance factors. Antimicrob Agents Chemother, 2003. 47(6): p. 1805-17.

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Molecular Weight (MW)207.27
Molecular FormulaC12H17NO2
CAS No.29342-05-0
Storage-20℃ for 3 years in powder formr
-80℃ for 2 years in solvent
Solubility In VitroDMSO: 42 mg/mL (202.6 mM)r
Water: <1 mg/mLr
Ethanol: 42 mg/mL (202.6 mM)
SMILES CodeCC1=CC(=O)N(C(=C1)C2CCCCC2)O
SynonymsCiclopirox; Penlac; Batrafen; Ciclopiroxum; Loprox; HOE 296; HOE296; HOE-296; Ciclopirox olamine
ProtocolIn VitroIn 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
These protocols are for reference only. InvivoChem does not independently validate these methods.
Preparing Stock Solutions
Solvent volume to be added Mass (the weight of a compound)
Mother liquor concentration 1mg5mg10mg20mg
1mM4.8246 mL24.1231 mL48.2462 mL96.4925 mL
5mM0.9649 mL4.8246 mL9.6492 mL19.2985 mL
10mM0.4825 mL2.4123 mL4.8246 mL9.6492 mL
20mM0.2412 mL1.2062 mL2.4123 mL4.8246 mL
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Concentration(start) × Volume(start) = Concentration(final) × Volume(final)

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Step Two: Enter the in vivo formulation
%DMSO + % + %Tween 80 + %ddH2O

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Method for preparing DMSO master liquid: mg drug pre-dissolved in µL DMSO(Master liquid concentration mg/mL) ,Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation: Take µL DMSO master liquid, next add µL PEG300, mix and clarify, next add µL Tween 80,mix and clarify, next add µL ddH2O,mix and clarify.
Note:
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