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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)
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.
Size Price Stock Qty
100mg
250mg
500mg
1g
Other Sizes

Other Forms of Ciclopirox (HOE 296):

  • Ciclopirox ethanolamine (HOE 296)
  • Ciclopirox-d11 sodium
  • Ciclopirox-d11 (HOE296b-d11)
  • Ciclopirox-d11 β-D-Glucuronide
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
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Rapidly absorbed after oral administration. Mean absorption of ciclopirox after application to nails of all twenty digits and adjacent 5 millimeters of skin once daily for 6 months in patients with dermatophytic onychomycoses was less than 5% of the applied dose. Ciclopirox olamine also penetrates into hair and through the epidermis and hair follicles into sebaceous glands and dermis.
Most of the compound is excreted either unchanged or as glucuronide. After oral administration of 10 mg of radiolabeled drug (14C-ciclopirox) to healthy volunteers, approximately 96% of the radioactivity was excreted renally within 12 hours of administration. Ninety-four percent of the renally excreted radioactivity was in the form of glucuronides.
Metabolism / Metabolites
Glucuronidation is the main metabolic pathway of ciclopirox.
Glucuronidation is the main metabolic pathway of ciclopirox.
Route of Elimination: Most of the compound is excreted either unchanged or as glucuronide. After oral administration of 10 mg of radiolabeled drug (14C-ciclopirox) to healthy volunteers, approximately 96% of the radioactivity was excreted renally within 12 hours of administration. Ninety-four percent of the renally excreted radioactivity was in the form of glucuronides.
Half Life: 1.7 hours for 1% topical solution.
Biological Half-Life
1.7 hours for 1% topical solution.
Toxicity/Toxicokinetics
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
Topical ciclopirox has not been studied during breastfeeding. Because only about 1.3% is absorbed after topical application, it is considered a low risk to the nursing infant.[1] Avoid application to the nipple area and ensure that the infant's skin does not come into direct contact with the areas of skin that have been treated. Only water-miscible cream or gel products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking.[2]
◉ Effects in Breastfed Infants
Relevant published information was not found as of the revision date.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.
Protein Binding
Protein binding is 94-97% following topical administration.
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.

Additional Infomation
Ciclopirox is a cyclic hydroxamic acid that is 1-hydroxypyridin-2(1H)-one in which the hydrogens at positions 4 and 6 are substituted by methyl and cyclohexyl groups, respectively. A broad spectrum antigfungal agent, it also exhibits antibacterial activity against many Gram-positive and Gram-negative bacteria, and has anti-inflammatory properties. It is used a a topical treatment of fungal skin and nail infections. It has a role as an antibacterial agent and an antiseborrheic. It is a pyridone, a cyclic hydroxamic acid and a hydroxypyridone antifungal drug.
Ciclopirox olamine (used in preparations called Batrafen, Loprox, Mycoster, Penlac and Stieprox) is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. In particular, the agent is especially effective in treating Tinea versicolor.
The mechanism of action of ciclopirox is as a Protein Synthesis Inhibitor. The physiologic effect of ciclopirox is by means of Decreased DNA Replication, and Decreased Protein Synthesis, and Decreased RNA Replication.
Ciclopirox is a synthetic, broad-spectrum antifungal agent with additional antibacterial and anti-inflammatory activities. Ciclopirox exerts its action by binding to and chelating trivalent cations, such as Fe3+ and Al3+, thereby inhibiting the availability of essential co-factors for enzymes. This may lead to a loss of activity of enzymes that are essential for cellular metabolism, organization of cell wall structure and other crucial cell functions. In addition, ciclopirox exerts its anti-inflammatory activity by inhibiting 5-lipoxygenase and cyclooxygenase (COX).
Ciclopirox is only found in individuals that have used or taken this drug. It is a synthetic antifungal agent for topical dermatologic use. [Wikipedia] Unlike antifungals such as itraconazole and terbinafine, which affect sterol synthesis, ciclopirox is thought to act through the chelation of polyvalent metal cations, such as Fe3+ and Al3+. These cations inhibit many enzymes, including cytochromes, thus disrupting cellular activities such as mitochondrial electron transport processes and energy production. Ciclopirox also appears to modify the plasma membrane of fungi, resulting in the disorganization of internal structures. The anti-inflammatory action of ciclopirox is most likely due to inhibition of 5-lipoxygenase and cyclooxygenase. Ciclopirox may exert its effect by disrupting DNA repair, cell division signals and structures (mitotic spindles) as well as some elements of intracellular transport.
A cyclohexane and pyridinone derivative that is used for the treatment of fungal infections of the skin and nails, and for treatment of VAGINAL YEAST INFECTIONS.
See also: Ciclopirox Olamine (has salt form); Ciclopirox; clobetasol propionate (component of); Ciclopirox; fluconazole; terbinafine (component of).
Drug Indication
Used as a topical treatment in immunocompetent patients with mild to moderate onychomycosis of fingernails and toenails without lunula involvement, due to Trichophyton rubrum.
FDA Label
Mechanism of Action
Unlike antifungals such as itraconazole and terbinafine, which affect sterol synthesis, ciclopirox is thought to act through the chelation of polyvalent metal cations, such as Fe3+ and Al3+. These cations inhibit many enzymes, including cytochromes, thus disrupting cellular activities such as mitochondrial electron transport processes and energy production. Ciclopirox also appears to modify the plasma membrane of fungi, resulting in the disorganization of internal structures. The anti-inflammatory action of ciclopirox is most likely due to inhibition of 5-lipoxygenase and cyclooxygenase. ciclopirox may exert its effect by disrupting DNA repair, cell division signals and structures (mitotic spindles) as well as some elements of intracellular transport.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H17NO2
Molecular Weight
207.27
Exact Mass
207.125
Elemental Analysis
C, 69.54; H, 8.27; N, 6.76; O, 15.44
CAS #
29342-05-0
Related CAS #
Ciclopirox olamine;41621-49-2;Ciclopirox olamine;41621-49-2;Ciclopirox-d11;Ciclopirox-d11 sodium
PubChem CID
2749
Appearance
White to off-white solid powder.
Density
1.2±0.1 g/cm3
Boiling Point
350.0±25.0 °C at 760 mmHg
Melting Point
1440C
Flash Point
165.5±23.2 °C
Vapour Pressure
0.0±1.7 mmHg at 25°C
Index of Refraction
1.582
LogP
2.59
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Heavy Atom Count
15
Complexity
325
Defined Atom Stereocenter Count
0
SMILES
O([H])N1C(C([H])=C(C([H])([H])[H])C([H])=C1C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H])=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)
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.06 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (12.06 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (12.06 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05809297 Not yet recruiting Drug: Ciclopirox Hydroxypropyl Chitosan
(HPCH) Nail Lacquer
Onychomycosis Universidad Complutense de Madrid September 1, 2023 Phase 4
NCT02679911 Completed
Has Results
Drug: Loceryl NL
Drug: Ciclopirox NL
Foot Dermatoses Galderma R&D September 2015 Phase 4
NCT00990587 Completed Drug: Ciclopirox Olamine Hematologic Malignancy
Acute Lymphocytic Leukemia
University Health Network, Toronto October 2009 Phase 1
NCT01646580 Terminated Drug: ciclopirox Dermatomycoses Ferrer Internacional S.A. October 2008 Phase 4
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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