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Identification
NameCiclopirox
Accession NumberDB01188  (APRD00871)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionCiclopirox 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
LoproxKitMedimetriks Pharmaceuticals, Inc.2016-06-13Not applicableUs
LoproxShampoo10 mg/.96mLTopicalMedicis Pharmaceutical Corp2003-03-20Not applicableUs
LoproxSuspension7.7 mg/mLTopicalMedimetriks Pharmaceuticals, Inc.2016-10-14Not applicableUs
LoproxKitMedimetriks Pharmaceuticals, Inc.2016-10-14Not applicableUs
LoproxCream7.7 mg/gTopicalMedimetriks Pharmaceuticals, Inc.2016-01-14Not 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
CiclodanCream7.7 mg/gTopicalMedimetriks Pharmaceuticals, Inc.2012-06-15Not applicableUs
CiclodanSolution2.28 g/mLTopicalMedimetriks Pharmaceuticals, Inc.2011-04-10Not applicableUs
CiclodanKitMedimetriks Pharmaceuticals, Inc.2012-06-15Not applicableUs
CiclodanSolution2.28 g/mLTopicalMedimetriks Pharmaceuticals, Inc.2011-04-10Not applicableUs
CiclopiroxSolution71.3 mg/mLTopicalRebel Distributors Corp.2007-09-18Not applicableUs
CiclopiroxSolution80 mg/mLTopicalHarris Pharmaceutical, Inc.2007-09-19Not applicableUs
CiclopiroxShampoo10 mg/.96mLTopicalActavis Pharma, Inc.2012-12-12Not applicableUs
CiclopiroxGel7.7 mg/gTopicalPaddock Laboratories, LLC2009-01-07Not applicableUs
CiclopiroxSolution80 mg/mLTopicalPhysicians Total Care, Inc.2009-09-04Not applicableUs
CiclopiroxSolution80 mg/mLTopicalPreferred Pharmaceuticals, Inc.2016-11-03Not applicableUs
CiclopiroxLotion7.7 mg/mLTopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2004-08-06Not applicableUs
CiclopiroxSuspension7.7 mg/mLTopicalTaro Pharmaceuticals U.S.A., Inc.2005-08-10Not applicableUs
CiclopiroxShampoo1 g/100mLTopicalPerrigo New York Inc2010-02-17Not applicableUs
CiclopiroxShampoo10 mg/.96mLTopicalTaro Pharmaceuticals, Inc.2011-02-23Not applicableUs
CiclopiroxGel7.7 mg/gTopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2008-06-10Not applicableUs
CiclopiroxShampoo10 mg/.96mLTopicalTaro Pharmaceuticals U.S.A., Inc.2011-02-23Not applicableUs
CiclopiroxSolution80 mg/gTopicalSandoz2007-09-18Not applicableUs
CiclopiroxSolution80 mg/mLTopicalVersa Pharm Incorporated2010-03-20Not applicableUs
CiclopiroxSolution80 mg/mLTopicalPerrigo New York Inc2007-09-19Not applicableUs
CiclopiroxGel7.7 mg/gTopicalGlenmark Pharmaceuticals Inc., Usa2012-02-29Not applicableUs
CiclopiroxSolution80 mg/mLTopicalG&W Laboratories, Inc.2007-05-22Not applicableUs
CiclopiroxShampoo10 mg/.96mLTopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2010-05-25Not applicableUs
CiclopiroxSolution71.3 mg/mLTopicalHi Tech Pharmacal Co., Inc.2007-09-18Not applicableUs
CiclopiroxSolution80 mg/mLTopicalTaro Pharmaceuticals U.S.A., Inc.2016-04-04Not applicableUs
Ciclopirox OlamineCream7.7 mg/gTopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2004-12-29Not applicableUs
Ciclopirox OlamineCream7.7 mg/gTopicalTaro Pharmaceuticals U.S.A., Inc.2005-04-12Not applicableUs
Ciclopirox OlamineSuspension7.7 mg/100mLTopicalPerrigo New York Inc2006-12-29Not applicableUs
Ciclopirox OlamineCream7.7 mg/gTopicalDispensing Solutions, Inc.2009-11-13Not applicableUs
Ciclopirox OlamineCream7.7 mg/gTopicalG&W Laboratories, Inc.2007-05-22Not applicableUs
Ciclopirox OlamineCream7.7 mg/gTopicalGlenmark Pharmaceuticals Inc., Usa2009-11-13Not applicableUs
Ciclopirox OlamineCream7.7 mg/gTopicalLake Erie Medical DBA Quality Care Products LLC2010-11-03Not applicableUs
Ciclopirox OlamineCream7.7 mg/gTopicalPerrigo New York Inc2006-07-19Not applicableUs
Ciclopirox OlamineCream7.7 mg/gTopicalPhysicians Total Care, Inc.2005-04-01Not 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 KeySCKYRAXSEDYPSA-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
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.
Structured Indications
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Sodium/potassium-transporting ATPase subunit alpha-1Proteinyes
binder
HumanP05023 details
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
Interactions
Drug Interactions
DrugInteractionDrug group
AmlodipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Ciclopirox.Approved, Investigational
AmrinoneThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Amrinone.Approved
AzelnidipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Azelnidipine.Approved
AzimilideThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Azimilide.Investigational
BarnidipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Barnidipine.Approved
BenidipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Benidipine.Approved
BepridilThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Bepridil.Approved, Withdrawn
BuspironeThe metabolism of Buspirone can be decreased when combined with Ciclopirox.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Ciclopirox.Approved, Investigational
CaiThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Cai.Investigational
CilnidipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Cilnidipine.Approved
CinnarizineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Cinnarizine.Approved
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Ciclopirox.Approved, Investigational, Withdrawn
ClevidipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Clevidipine.Approved
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Ciclopirox.Approved, Investigational
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Ciclopirox.Approved, Investigational, Vet Approved
DarodipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Darodipine.Experimental
DidanosineDidanosine can cause a decrease in the absorption of Ciclopirox resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DiltiazemThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Diltiazem.Approved
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Ciclopirox.Approved, Investigational
DofetilideThe metabolism of Dofetilide can be decreased when combined with Ciclopirox.Approved
DotarizineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Dotarizine.Investigational
EfonidipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Efonidipine.Approved
EperisoneThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Eperisone.Approved, Investigational
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Ciclopirox.Approved
FelodipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Felodipine.Approved, Investigational
FendilineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Fendiline.Withdrawn
FlunarizineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Flunarizine.Approved
FosphenytoinThe serum concentration of Ciclopirox can be decreased when it is combined with Fosphenytoin.Approved
GabapentinThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Gabapentin.Approved, Investigational
GallopamilThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Gallopamil.Investigational
IsradipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Isradipine.Approved
LacidipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Lacidipine.Approved
LamotrigineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Lamotrigine.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Lercanidipine.Approved, Investigational
LosartanThe metabolism of Losartan can be decreased when combined with Ciclopirox.Approved
Magnesium SulfateThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Magnesium Sulfate.Approved, Vet Approved
ManidipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Manidipine.Approved
MibefradilThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Mibefradil.Withdrawn
NaftopidilThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Naftopidil.Investigational
NicardipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Nicardipine.Approved
NifedipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Nifedipine.Approved
NiguldipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Niguldipine.Experimental
NiludipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Niludipine.Experimental
NilvadipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Nilvadipine.Approved
NimesulideThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Nimesulide.Approved, Withdrawn
NimodipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Nimodipine.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Nitrendipine.Approved
PerhexilineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Perhexiline.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Ciclopirox.Approved, Vet Approved
PimozideCiclopirox may increase the arrhythmogenic activities of Pimozide.Approved
PinaveriumThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Pinaverium.Approved
PregabalinThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Pregabalin.Approved, Illicit, Investigational
PrenylamineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Prenylamine.Withdrawn
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Ciclopirox.Approved, Vet Approved
QuinidineThe metabolism of Quinidine can be decreased when combined with Ciclopirox.Approved
RanolazineThe metabolism of Ranolazine can be decreased when combined with Ciclopirox.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Ciclopirox.Approved
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Ciclopirox.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Ciclopirox.Approved
RisedronateThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Risedronate.Approved, Investigational
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Ciclopirox.Approved
SucralfateSucralfate can cause a decrease in the absorption of Ciclopirox resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Ciclopirox.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Ciclopirox.Approved, Investigational
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Tolfenamic Acid.Approved
TranilastThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Tranilast.Approved, Investigational
VerapamilThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Verapamil.Approved
VinpocetineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Vinpocetine.Investigational
XylometazolineThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Xylometazoline.Approved
ZiconotideThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Ciclopirox.Approved
Food InteractionsNot 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 CodesG01AX12D01AE14
AHFS Codes
  • 84:04.08.20
PDB EntriesNot Available
FDA labelDownload (422 KB)
MSDSDownload (74.1 KB)
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
GelTopical7.7 mg/g
Kit
LotionTopical7.7 mg/mL
ShampooTopical1 g/100mL
ShampooTopical10 mg/.96mL
SolutionTopical71.3 mg/mL
SolutionTopical80 mg/mL
SolutionTopical80 mg/g
SuspensionTopical7.7 mg/mL
CreamTopical7.7 mg/g
SuspensionTopical7.7 mg/100mL
SolutionTopical2.28 g/mL
CreamTopical1 %
CreamTopical10 mg
LotionTopical1 %
LotionTopical10 mg
Kit
SolutionTopical8 %
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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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

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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on December 05, 2016 02:42