Identification
- Summary
Ciclopirox is a broad-spectrum topical antifungal agent used to treat mild to moderate onychomycosis of fingernails and toenails in immunocompetent patients.
- Brand Names
- Ciclodan, Cnl8, Loprox, Penlac, Stieprox
- Generic Name
- Ciclopirox
- DrugBank Accession Number
- DB01188
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Ciclopirox (DB01188)
- Weight
- Average: 207.2689
Monoisotopic: 207.125928793 - Chemical Formula
- C12H17NO2
- Synonyms
- 6-cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone
- Ciclopirox
- Ciclopiroxum
- External IDs
- HOE 296B
- HOE-296B
Pharmacology
- 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.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Fungal skin infection ••• ••• •••••••• Treatment of Seborrheic dermatitis of the scalp •••••••••••• ••••••• Treatment of Tinea corporis •••••••••••• Treatment of Tinea cruris •••••••••••• Treatment of Tinea pedis •••••••••••• - Contraindications & Blackbox Warnings
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Ciclopirox is a broad-spectrum antifungal medication that also has antibacterial and anti-inflammatory properties. Its main mode of action is thought to be its high affinity for trivalent cations, which inhibit essential co-factors in enzymes. Ciclopirox exhibits either fungistatic or fungicidal activity in vitro against a broad spectrum of fungal organisms, such as dermatophytes, yeasts, dimorphic fungi, eumycetes, and actinomycetes. In addition to its broad spectrum of action, ciclopirox also exerts antibacterial activity against many Gram-positive and Gram-negative bacteria. Furthermore, the anti-inflammatory effects of ciclopirox have been demonstrated in human polymorphonuclear cells, where ciclopirox has inhibited the synthesis of prostaglandin and leukotriene. Ciclopirox can also exhibit its anti-inflammatory effects by inhibiting the formation of 5-lipoxygenase and cyclooxygenase.
- 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.
Target Actions Organism ASodium/potassium-transporting ATPase subunit alpha-1 binderHumans - Absorption
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.
- Volume of distribution
Not Available
- Protein binding
Protein binding is 94-97% following topical administration.
- Metabolism
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.
- Clearance
Not Available
- Adverse Effects
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Oral LD50 in rat is >10 ml/kg. Symptoms of overexposure include drowsiness and headache.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.No interactions found.
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Ciclopirox olamine 50MD4SB4AP 41621-49-2 MBRHNTMUYWQHMR-UHFFFAOYSA-N - International/Other Brands
- Batrafen (Sanofi) / Mycoster (Pierre Fabre) / Stieprox (Stiefel)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ciclopirox Solution 8 g/100mL Topical Dr Marc's Manufacturing And Sales 2018-01-30 2018-04-17 US 
Ciclopirox Gel 7.7 mg/1g Topical Alvogen Inc. 2017-02-14 2021-09-01 US Ciclopirox Gel 7.7 mg/1g Topical Paddock Laboratories, Inc. 2009-01-15 2013-03-24 US Ciclopirox Kit; Solution 2.28 g/1mL Topical Acella Pharmaceuticals, LLC 2011-10-10 Not applicable US Ciclopirox 3% Gel 3 g/100g Topical Sincerus Florida, LLC 2019-05-20 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-ciclopirox Solution 8 % w/w Topical Apotex Corporation 2008-04-18 Not applicable Canada 
Ciclodan Kit 7.7 mg/1g Topical Medimetriks Pharmaceuticals 2012-06-15 2017-12-01 US Ciclodan Solution 2.28 g/1mL Topical Medimetriks Pharmaceuticals, Inc. 2011-04-10 2019-11-11 US Ciclodan Cream 7.7 mg/1g Topical Medimetriks Pharmaceuticals 2012-06-15 2017-12-01 US Ciclodan Solution 2.28 g/1mL Topical Medimetriks Pharmaceuticals, Inc. 2011-04-10 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image STIEPROX LIQUID Liquid GLAXOSMITHKLINE CONSUMER HEALTHCARE SDN. BHD. 2020-09-08 Not applicable Malaysia 
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Pedipirox-4 Nail Kit Ciclopirox (71.3 mg/1mL) + Ciclopirox (71.3 mg/1mL) Kit Topical Pedinol Pharmacal, Inc. 2012-02-03 2015-04-30 US Pedipirox-4 Nail Kit Ciclopirox (71.3 mg/1mL) + Ciclopirox (71.3 mg/1mL) Kit Topical Pedinol Pharmacal, Inc. 2012-02-03 2015-04-30 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Ciclomazole Ciclopirox (80 mg/1mL) + Betamethasone dipropionate (0.5 mg/1g) + Clotrimazole (10 mg/1g) Cream; Kit; Solution Topical PureTek Corporation 2020-12-17 Not applicable US Ciclopirox Ciclopirox (2.28 g/1mL) Kit; Solution Topical Acella Pharmaceuticals, LLC 2011-10-10 Not applicable US Ciclopirox Ciclopirox (80 mg/1mL) + Tocopherol (50 mg/1) Kit Topical Acella Pharmaceuticals, LLC 2008-10-27 2015-05-31 US Ciclopirox Ciclopirox (8 g/100mL) Solution Topical Dr Marc's Manufacturing And Sales 2018-01-30 2018-04-17 US Ciclopirox 0.77% / Salicylic Acid 2% Ciclopirox olamine (1 g/100g) + Salicylic acid (2 g/100g) Shampoo Topical Sincerus Florida, LLC 2019-05-17 Not applicable US
Categories
- ATC Codes
- D01AE14 — Ciclopirox
- D01AE — Other antifungals for topical use
- D01A — ANTIFUNGALS FOR TOPICAL USE
- D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- Drug Categories
- Anti-Infective Agents
- Antifungal Agents
- Antifungals for Dermatological Use
- Antifungals for Topical Use
- Cyclohexanes
- Cycloparaffins
- Decreased DNA Replication
- Decreased Protein Synthesis
- Decreased RNA Replication
- Dermatologicals
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Hydroxypyridones
- Protein Synthesis Inhibitors
- Pyridines
- Pyridones
- Vaginal Creams, Foams, and Jellies
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyridinones. These are compounds containing a pyridine ring, which bears a ketone.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Hydropyridines
- Direct Parent
- Pyridinones
- Alternative Parents
- Methylpyridines / Dihydropyridines / Heteroaromatic compounds / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Dihydropyridine / Heteroaromatic compound / Hydrocarbon derivative / Lactam / Methylpyridine / Organic nitrogen compound / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- hydroxypyridone antifungal drug, pyridone, cyclic hydroxamic acid (CHEBI:453011)
- Affected organisms
- Humans and other mammals
- Yeast and other fungi
Chemical Identifiers
- UNII
- 19W019ZDRJ
- CAS number
- 29342-05-0
- InChI Key
- SCKYRAXSEDYPSA-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- 6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one
- SMILES
- CC1=CC(=O)N(O)C(=C1)C1CCCCC1
References
- Synthesis Reference
Lohaus, G.and Dittmar, W.; U.S. Patents 3,972,888; August 3, 1976; and 3,883,545; May 13, 1975; both assigned to Hoechst A .G.
- General References
- Niewerth M, Kunze D, Seibold M, Schaller M, Korting HC, Hube B: 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 Jun;47(6):1805-17. [Article]
- Sigle HC, Thewes S, Niewerth M, Korting HC, Schafer-Korting M, Hube B: Oxygen accessibility and iron levels are critical factors for the antifungal action of ciclopirox against Candida albicans. J Antimicrob Chemother. 2005 May;55(5):663-73. Epub 2005 Mar 24. [Article]
- FDA Approved Drug Products: LOPROX (ciclopirox) cream, gel, and suspension [Link]
- FDA Approved Drug Products: LOPROX (ciclopirox) shampoo [Link]
- FDA Approved Drug Products: Penlac (ciclopirox) solution [Link]
- External Links
- Human Metabolome Database
- HMDB0015319
- KEGG Drug
- D03488
- PubChem Compound
- 2749
- PubChem Substance
- 46506333
- ChemSpider
- 2647
- BindingDB
- 66087
- 21090
- ChEBI
- 453011
- ChEMBL
- CHEMBL1413
- ZINC
- ZINC000000001145
- Therapeutic Targets Database
- DAP000466
- PharmGKB
- PA164747060
- PDBe Ligand
- B4O
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Ciclopirox
- PDB Entries
- 6j10
- FDA label
- Download (422 KB)
- MSDS
- Download (74.1 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Foot Dermatoses 1 4 Completed Treatment Onychomycosis 1 4 Not Yet Recruiting Treatment Onychomycosis 1 4 Terminated Not Available Fungal skin infection 1 4 Unknown Status Treatment Onychomycosis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Actavis Group
- Apotex Inc.
- A-S Medication Solutions LLC
- Brookstone Pharmaceuticals
- Cipla Ltd.
- Contract Pharm
- Dermik Labs
- DispenseXpress Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- E. Fougera and Co.
- G & W Labs
- Glenmark Generics Ltd.
- Groupe Parima Inc.
- Harris Pharmaceutical Inc.
- Hi Tech Pharmacal Co. Inc.
- JSJ Pharmaceuticals Inc.
- Medicis Pharmaceutical Co.
- Medisca Inc.
- Nycomed Inc.
- Paddock Labs
- Patheon Inc.
- Perrigo Co.
- Pharmedix
- Physicians Total Care Inc.
- Rebel Distributors Corp.
- Sandoz
- Sanofi-Aventis Inc.
- Taro Pharmaceuticals USA
- Teva Pharmaceutical Industries Ltd.
- Tolmar Inc.
- Dosage Forms
Form Route Strength Cream Cutaneous 1 % Cream Cutaneous 10 mg/g Powder Topical 1 % Solution Topical 10 mg/g Solution Topical 8 % Solution Topical Cream Vaginal 1 g Gel Topical 770 mg Lotion Topical Cream Topical 1.000 g Spray Topical 1 % Shampoo Topical Solution Topical 10 mg/mL Kit Topical 7.7 mg/1g Cream; kit; solution Topical Gel Topical 7.7 mg/1g Gel Topical 7.70 mg/1g Kit Topical Kit; solution Topical 2.28 g/1mL Lotion Topical 7.7 mg/1mL Shampoo Topical 1 g/100mL Shampoo Topical 10 mg/0.96mL Shampoo Topical 10 mg/.96mL Solution Topical 71.3 mg/1mL Solution Topical 8 g/100mL Solution Topical 80 mg/1mL Solution Topical 80 mg/1g Shampoo Topical Gel Topical 3 g/100g Cream Topical Solution Topical Solution Vaginal Cream Topical 7.7 mg/1g Suspension Topical 7.70 mg/100mL Spray Cutaneous Cream Topical 10 mg/mL Insert Vaginal 1 % Solution Topical 2.28 g/1mL Aerosol, foam Vaginal 2 % Cream Vaginal 1 % Insert Vaginal 100 MG Solution Vaginal 0.2 % Solution Topical 8 g Cream Topical 1 % w/w Gel Cutaneous 0.770 g Kit Topical 7.7 mg/1mL Lotion Topical 1 % w/w Suspension Topical 7.7 mg/1mL Cream Topical 10 mg / g Lotion Topical 1 % Lotion Topical 10 mg / g Cream Topical 1 % Cream Vaginal 78 G Emulsion Topical 1 % Emulsion Topical 30 G Lotion Cutaneous 1 % Solution Topical 1 % Aerosol, foam Vaginal Cream Topical Cream Vaginal Insert Vaginal Solution Cutaneous Cream Topical 10 mg/g Cream Vaginal 10 mg/g Solution Cutaneous 0.069 g Solution Topical 6.92 g Solution Topical 8 % w/w Solution Topical 80 MG/G Cream Topical 1 g Lotion Topical 1 g Solution Topical 1 g Solution Topical 80 mg Liquid Shampoo Topical 1.5 % Emulsion Topical 1.5 g - Prices
Unit description Cost Unit Loprox 0.77% Gel 100 gm Jar 447.91USD jar Loprox 0.77% Cream 90 gm Tube 266.01USD tube Ciclopirox 0.77% Gel 100 gm Tube 252.1USD tube Penlac 8% Solution 6.6ml Bottle 244.87USD bottle Loprox 1% Shampoo 120ml Bottle 235.49USD bottle Loprox 0.77% Suspension 60ml Bottle 223.11USD bottle Loprox 0.77% Gel 45 gm Tube 219.21USD tube Ciclopirox 8% Solution 6.6ml Bottle 177.27USD bottle Loprox 0.77% Gel 30 gm Tube 155.63USD tube Ciclopirox 1% Shampoo 120ml Bottle 153.24USD bottle Ciclopirox Olamine 0.77% Cream 90 gm Tube 128.77USD tube Ciclopirox 0.77% Gel 45 gm Tube 125.88USD tube Loprox 0.77% Cream 30 gm Tube 107.88USD tube Ciclopirox Olamine 0.77% Suspension 60ml Bottle 100.0USD bottle Ciclopirox 0.77% Gel 30 gm Tube 83.91USD tube Ciclopirox Olamine 0.77% Cream 30 gm Tube 53.24USD tube Ciclopirox Olamine 0.77% Suspension 30ml Bottle 50.48USD bottle Penlac 8% solution 39.24USD ml Ciclopirox Olamine 0.77% Cream 15 gm Tube 29.8USD tube Ciclopirox olamine powder 10.47USD g Loprox 0.77% cream 2.96USD g Ciclopirox 0.77% cream 1.64USD g Loprox 1 % Cream 0.53USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7026337 No 2006-04-11 2016-11-21 US US7018656 No 2006-03-28 2018-09-05 US US7981909 No 2011-07-19 2017-09-16 US US8227490 No 2012-07-24 2017-09-16 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 143 Lohaus, G.and Dittmar, W.; U.S. Patents 3,972,888; August 3, 1976; and 3,883,545; May 13, 1975; both assigned to Hoechst A .G. logP 2.3 Not Available - Predicted Properties
Property Value Source Water Solubility 1.41 mg/mL ALOGPS logP 2.15 ALOGPS logP 2.22 Chemaxon logS -2.2 ALOGPS pKa (Strongest Acidic) 6.84 Chemaxon pKa (Strongest Basic) -6.2 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 40.54 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 60.91 m3·mol-1 Chemaxon Polarizability 23.13 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9952 Blood Brain Barrier + 0.9892 Caco-2 permeable + 0.5125 P-glycoprotein substrate Non-substrate 0.731 P-glycoprotein inhibitor I Non-inhibitor 0.7715 P-glycoprotein inhibitor II Non-inhibitor 0.9497 Renal organic cation transporter Non-inhibitor 0.8234 CYP450 2C9 substrate Non-substrate 0.6075 CYP450 2D6 substrate Non-substrate 0.8043 CYP450 3A4 substrate Substrate 0.6051 CYP450 1A2 substrate Inhibitor 0.5732 CYP450 2C9 inhibitor Non-inhibitor 0.5951 CYP450 2D6 inhibitor Non-inhibitor 0.8998 CYP450 2C19 inhibitor Non-inhibitor 0.6613 CYP450 3A4 inhibitor Non-inhibitor 0.873 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5218 Ames test Non AMES toxic 0.6085 Carcinogenicity Non-carcinogens 0.9004 Biodegradation Not ready biodegradable 0.802 Rat acute toxicity 2.3495 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9727 hERG inhibition (predictor II) Non-inhibitor 0.5929
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-02vi-1900000000-b0302ddc025a747a3484 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-2690000000-d99ab83d27dce32743cf Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0190000000-883d6f12796ee4fed765 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a59-9730000000-b6d0b65d6a115e2d9eb4 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-05fr-1920000000-f11c53dffc84d74e7899 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0apl-9500000000-9266a88854401b1b7c37 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-066u-9800000000-9f2b671ea01e634ddc8a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 153.0397947 predictedDarkChem Lite v0.1.0 [M-H]- 145.71362 predictedDeepCCS 1.0 (2019) [M+H]+ 154.0818947 predictedDarkChem Lite v0.1.0 [M+H]+ 148.1092 predictedDeepCCS 1.0 (2019) [M+Na]+ 153.2505947 predictedDarkChem Lite v0.1.0 [M+Na]+ 154.14458 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- Steroid hormone binding
- Specific Function
- This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates th...
- Gene Name
- ATP1A1
- Uniprot ID
- P05023
- Uniprot Name
- Sodium/potassium-transporting ATPase subunit alpha-1
- Molecular Weight
- 112895.01 Da
References
- Niewerth M, Kunze D, Seibold M, Schaller M, Korting HC, Hube B: 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 Jun;47(6):1805-17. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55