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Identification
NameCiclopirox
Accession NumberDB01188  (APRD00871)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Ciclopirox olamine (used in preparations called Batrafen, Loprox, Mycoster, Penlac and Stieprox) is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against Tinea versicolor. [Wikipedia]

Structure
Thumb
Synonyms
6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone
Ciclopiroxum
External Identifiers
  • HOE 296B
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ciclopiroxshampoo10 mg/.96mLtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2012-11-19Not applicableUs
Ciclopirox Topical Solutionsolution8 %topicalSterimax Inc2013-09-16Not applicableCanada
Loproxcream7.7 mg/gtopicalMedimetriks Pharmaceuticals, Inc.2016-01-14Not applicableUs
Loproxshampoo10 mg/.96mLtopicalMedicis Pharmaceutical Corp2003-03-20Not applicableUs
Loprox Creamcream1 %topicalValeant Canada Lp Valeant Canada S.E.C.1996-12-03Not applicableCanada
Loprox Cream 1%cream10 mgtopicalHoechst Roussel Canada Inc.1994-12-311998-08-12Canada
Loprox Crm 1%cream10 mgtopicalHoechst Canada Inc.1985-12-311996-08-29Canada
Loprox Lotionlotion1 %topicalValeant Canada Lp Valeant Canada S.E.C.1997-03-24Not applicableCanada
Loprox Lotion 1.0%lotion1 %topicalHoechst Roussel Canada Inc.1995-12-311999-08-11Canada
Loprox Lotion 1%lotion10 mgtopicalHoechst Canada Inc.1990-12-311996-08-29Canada
Penlacsolution8 %topicalValeant Canada Lp Valeant Canada S.E.C.2004-07-28Not applicableCanada
Penlacsolution80 mg/mLtopicalValeant Pharmaceuticals North America LLC2013-05-01Not applicableUs
PMS-ciclopiroxsolution8 %topicalPharmascience Inc2013-10-22Not applicableCanada
Stieprox Shampooshampoo1.5 %topicalGlaxosmithkline Inc2003-11-17Not applicableCanada
Taro-ciclopiroxsolution8 %topicalTaro Pharmaceuticals Inc2011-10-25Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-ciclopiroxsolution8 %topicalApotex Inc2008-04-18Not applicableCanada
CiclodankitMedimetriks Pharmaceuticals, Inc.2012-06-15Not applicableUs
Ciclodancream7.7 mg/gtopicalMedimetriks Pharmaceuticals, Inc.2012-06-15Not applicableUs
Ciclodansolution2.28 g/mLtopicalMedimetriks Pharmaceuticals, Inc.2011-04-10Not applicableUs
Ciclodansolution2.28 g/mLtopicalMedimetriks Pharmaceuticals, Inc.2011-04-10Not applicableUs
Ciclopiroxsolution80 mg/mLtopicalTaro Pharmaceuticals U.S.A., Inc.2016-04-04Not applicableUs
Ciclopiroxsolution80 mg/mLtopicalVersa Pharm Incorporated2010-03-20Not applicableUs
Ciclopiroxshampoo1 g/100mLtopicalPerrigo New York Inc2010-02-17Not applicableUs
Ciclopiroxsolution80 mg/gtopicalSandoz2007-09-18Not applicableUs
Ciclopiroxshampoo10 mg/.96mLtopicalTaro Pharmaceuticals, Inc.2011-02-23Not applicableUs
Ciclopiroxsolution80 mg/mLtopicalPerrigo New York Inc2007-09-19Not applicableUs
Ciclopiroxsolution80 mg/mLtopicalG&W Laboratories, Inc.2007-05-22Not applicableUs
Ciclopiroxsolution80 mg/mLtopicalPhysicians Total Care, Inc.2009-09-04Not applicableUs
Ciclopiroxshampoo10 mg/.96mLtopicalWatson Laboratories, Inc.2012-12-12Not applicableUs
Ciclopiroxgel7.7 mg/gtopicalPaddock Laboratories, LLC2009-01-07Not applicableUs
Ciclopiroxgel7.7 mg/gtopicalGlenmark Pharmaceuticals Inc., Usa2012-02-29Not applicableUs
Ciclopiroxshampoo10 mg/.96mLtopicalTaro Pharmaceuticals U.S.A., Inc.2011-02-23Not applicableUs
Ciclopiroxshampoo10 mg/.96mLtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2010-05-25Not applicableUs
Ciclopiroxsuspension7.7 mg/mLtopicalTaro Pharmaceuticals U.S.A., Inc.2005-08-10Not applicableUs
Ciclopiroxgel7.7 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2008-06-10Not applicableUs
Ciclopiroxsolution80 mg/mLtopicalHarris Pharmaceutical, Inc.2007-09-19Not applicableUs
Ciclopiroxsolution71.3 mg/mLtopicalHi Tech Pharmacal Co., Inc.2007-09-18Not applicableUs
Ciclopiroxsolution71.3 mg/mLtopicalRebel Distributors Corp.2007-09-18Not applicableUs
Ciclopiroxlotion7.7 mg/mLtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2004-08-06Not applicableUs
Ciclopirox Olaminecream7.7 mg/gtopicalLake Erie Medical DBA Quality Care Products LLC2010-11-03Not applicableUs
Ciclopirox Olaminecream7.7 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2004-12-29Not applicableUs
Ciclopirox Olaminesuspension7.7 mg/100mLtopicalPerrigo New York Inc2006-12-29Not applicableUs
Ciclopirox Olaminecream7.7 mg/gtopicalG&W Laboratories, Inc.2007-05-22Not applicableUs
Ciclopirox Olaminecream7.7 mg/gtopicalPerrigo New York Inc2006-07-19Not applicableUs
Ciclopirox Olaminecream7.7 mg/gtopicalPhysicians Total Care, Inc.2005-04-01Not applicableUs
Ciclopirox Olaminecream7.7 mg/gtopicalGlenmark Pharmaceuticals Inc., Usa2009-11-13Not applicableUs
Ciclopirox Olaminecream7.7 mg/gtopicalDispensing Solutions, Inc.2009-11-13Not applicableUs
Ciclopirox Olaminecream7.7 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2005-04-12Not applicableUs
Cnl8solution2.28 g/mLtopicalInnocutis Holdings LLC2008-10-31Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CiclopiroxkitAcella Pharmaceuticals, LLC2009-07-01Not applicableUs
CiclopiroxkitAcella Pharmaceuticals, LLC2011-09-12Not applicableUs
International Brands
NameCompany
BatrafenSanofi
MycosterPierre Fabre
StieproxStiefel
Brand mixtures
NameLabellerIngredients
PedipakTotal Pharmacy Supply, Inc.
Salts
Name/CASStructureProperties
Ciclopirox olamine
ThumbNot applicableDBSALT001147
Categories
UNII19W019ZDRJ
CAS number29342-05-0
WeightAverage: 207.2689
Monoisotopic: 207.125928793
Chemical FormulaC12H17NO2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyridinones. These are compounds containing a pyridine ring, which bears a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassHydropyridines
Direct ParentPyridinones
Alternative Parents
Substituents
  • Methylpyridine
  • Pyridinone
  • Dihydropyridine
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationUsed as a topical treatment in immunocompetent patients with mild to moderate onychomycosis of fingernails and toenails without lunula involvement, due to Trichophyton rubrum.
PharmacodynamicsCiclopirox 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 actionUnlike 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.
Related Articles
AbsorptionRapidly 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 distributionNot Available
Protein bindingProtein binding is 94-97% following topical administration.
Metabolism

Glucuronidation is the main metabolic pathway of ciclopirox.

Route of eliminationMost 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 life1.7 hours for 1% topical solution.
ClearanceNot Available
ToxicityOral LD50 in rat is >10 ml/kg. Symptoms of overexposure include drowsiness and headache.
Affected organisms
  • Humans and other mammals
  • Yeast and other fungi
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9952
Blood Brain Barrier+0.9892
Caco-2 permeable+0.5125
P-glycoprotein substrateNon-substrate0.731
P-glycoprotein inhibitor INon-inhibitor0.7715
P-glycoprotein inhibitor IINon-inhibitor0.9497
Renal organic cation transporterNon-inhibitor0.8234
CYP450 2C9 substrateNon-substrate0.6075
CYP450 2D6 substrateNon-substrate0.8043
CYP450 3A4 substrateSubstrate0.6051
CYP450 1A2 substrateInhibitor0.5732
CYP450 2C9 inhibitorNon-inhibitor0.5951
CYP450 2D6 inhibitorNon-inhibitor0.8998
CYP450 2C19 inhibitorNon-inhibitor0.6613
CYP450 3A4 inhibitorNon-inhibitor0.873
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5218
Ames testNon AMES toxic0.6085
CarcinogenicityNon-carcinogens0.9004
BiodegradationNot ready biodegradable0.802
Rat acute toxicity2.3495 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9727
hERG inhibition (predictor II)Non-inhibitor0.5929
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Solutiontopical2.28 g/mL
Geltopical7.7 mg/g
Kit
Lotiontopical7.7 mg/mL
Shampootopical1 g/100mL
Shampootopical10 mg/.96mL
Solutiontopical71.3 mg/mL
Solutiontopical80 mg/g
Suspensiontopical7.7 mg/mL
Creamtopical7.7 mg/g
Suspensiontopical7.7 mg/100mL
Creamtopical1 %
Creamtopical10 mg
Lotiontopical1 %
Lotiontopical10 mg
Kit
Solutiontopical8 %
Solutiontopical80 mg/mL
Shampootopical1.5 %
Prices
Unit descriptionCostUnit
Loprox 0.77% Gel 100 gm Jar447.91USD jar
Loprox 0.77% Cream 90 gm Tube266.01USD tube
Ciclopirox 0.77% Gel 100 gm Tube252.1USD tube
Penlac 8% Solution 6.6ml Bottle244.87USD bottle
Loprox 1% Shampoo 120ml Bottle235.49USD bottle
Loprox 0.77% Suspension 60ml Bottle223.11USD bottle
Loprox 0.77% Gel 45 gm Tube219.21USD tube
Ciclopirox 8% Solution 6.6ml Bottle177.27USD bottle
Loprox 0.77% Gel 30 gm Tube155.63USD tube
Ciclopirox 1% Shampoo 120ml Bottle153.24USD bottle
Ciclopirox Olamine 0.77% Cream 90 gm Tube128.77USD tube
Ciclopirox 0.77% Gel 45 gm Tube125.88USD tube
Loprox 0.77% Cream 30 gm Tube107.88USD tube
Ciclopirox Olamine 0.77% Suspension 60ml Bottle100.0USD bottle
Ciclopirox 0.77% Gel 30 gm Tube83.91USD tube
Ciclopirox Olamine 0.77% Cream 30 gm Tube53.24USD tube
Ciclopirox Olamine 0.77% Suspension 30ml Bottle50.48USD bottle
Penlac 8% solution39.24USD ml
Ciclopirox Olamine 0.77% Cream 15 gm Tube29.8USD tube
Ciclopirox olamine powder10.47USD g
Loprox 0.77% cream2.96USD g
Ciclopirox 0.77% cream1.64USD g
Loprox 1 % Cream0.53USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7018656 No1998-09-052018-09-05Us
US7026337 No1996-11-212016-11-21Us
US7981909 No1997-09-162017-09-16Us
US8227490 No1997-09-162017-09-16Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point143Lohaus, 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.
logP2.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.41 mg/mLALOGPS
logP2.15ALOGPS
logP2.22ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)6.84ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area40.54 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity60.91 m3·mol-1ChemAxon
Polarizability23.12 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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
  1. 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. [PubMed:12760852 ]
  2. 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. [PubMed:15790671 ]
External Links
ATC CodesD01AE14G01AX12
AHFS Codes
  • 84:04.08.20
PDB EntriesNot Available
FDA labelDownload (422 KB)
MSDSDownload (74.1 KB)
Interactions
Drug InteractionsNo interactions found.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular Weight:
112895.01 Da
References
  1. 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. [PubMed:12760852 ]
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Drug created on June 13, 2005 07:24 / Updated on June 25, 2016 01:50