Ciclopirox (HOE 296)

Alias: Ciclopirox; Penlac; Batrafen; Ciclopiroxum; Loprox; HOE 296; HOE296; HOE-296; Ciclopirox olamine
Cat No.:V0186 Purity: ≥98%
Ciclopirox (HOE-296; LACQUER; Penlac), ahydroxypyrimidine analog, is an potent, synthetic and broad-spectrum antifungal agent used for topical dermatologic treatment of superficial mycoses.
Ciclopirox (HOE 296) Chemical Structure CAS No.: 29342-05-0
Product category: Fungal
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Ciclopirox (HOE 296):

  • Ciclopirox ethanolamine (HOE 296)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product 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.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
In an investigation aimed at deciphering the mechanism of Ciclopirox, a number of Saccharomyces cerevisiae mutants were examined and evaluated. According to findings from the interpretation of the effects of the drug treatment and mutation, Ciclopirox may work by interfering with DNA repair, mitotic spindles, and other cell division signals and structures, as well as certain aspects of intracellular transport[2].
A broad-spectrum antifungal with anti-inflammatory qualities, ciclopirox is effective against Malassezia spp., the yeast linked to seborrheic dermatitis[3].
ln Vivo
The 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.
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.
Animal Protocol
Different animal organ models including mouse skin wound model, rat kidney model and chicken chorioallantoic membrane model
References

[1]. Antimicrob Agents Chemother, 2003. 47(6): p. 1805-17.

[2]. Mol Cells, 2003. 15(1): p. 55-61.

[3]. J Dermatolog Treat, 2007. 18(2): p. 88-96.

[4]. FASEB J.2003 Apr;17(6):761-3

[5]. Br J Pharmacol.2005 Jun;145(4):469-76.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H17NO2
Molecular Weight
207.27
Exact Mass
207.13
Elemental Analysis
C, 69.54; H, 8.27; N, 6.76; O, 15.44
CAS #
29342-05-0
Appearance
White to off-white solid powder.
SMILES
CC1=CC(=O)N(C(=C1)C2CCCCC2)O
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
Chemical Name
6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one
Synonyms
Ciclopirox; Penlac; Batrafen; Ciclopiroxum; Loprox; HOE 296; HOE296; HOE-296; Ciclopirox olamine
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : 41~100 mg/mL ( 197.8~482.46 mM )
Ethanol : 41 mg/mL
Solubility (In Vivo)
5%DMSO + Corn oil: 3mg/ml (14.47mM) (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.8246 mL 24.1231 mL 48.2462 mL
5 mM 0.9649 mL 4.8246 mL 9.6492 mL
10 mM 0.4825 mL 2.4123 mL 4.8246 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution 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 stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Biological Data
  • 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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