Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H17NO2 |
Molecular Weight | 207.2689 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(=O)N(O)C(=C1)C2CCCCC2
InChI
InChIKey=SCKYRAXSEDYPSA-UHFFFAOYSA-N
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
Molecular Formula | C12H17NO2 |
Molecular Weight | 207.2689 |
Charge | 0 |
Count |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21022s004lbl.pdf
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21022s004lbl.pdf
Ciclopirox is an antifungal medication indicated for the treatment of seborrheic dermatitis (Loprox trade name) and onychomycosis of fingernails and toenails due to Trichophyton rubrum (Penlac trade name). The drug exerts its action by chelating Fe3+ and Al3+, resulting in the inhibition of the metal-dependent enzymes that are responsible for the degradation of peroxides within the fungal cell.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2366381 |
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Target ID: CHEMBL2363058 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | LOPROX Approved UseLoprox Shampoo is an antifungal indicated for the topical treatment of seborrheic dermatitis of the scalp in adults. Launch Date1982 |
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Curative | PENALC Approved UsePENLAC NAIL LACQUER (ciclopirox) Topical Solution, 8%, as a component of a comprehensive management program, is indicated as topical treatment in immunocompetent patients with mild to moderate onychomycosis of fingernails and toenails without lunula involvement, due to Trichophyton rubrum. Launch Date1999 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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25.02 ng/mL |
38.5 mg single, topical dose: 38.5 mg route of administration: Topical experiment type: SINGLE co-administered: |
CICLOPIROX blood | Homo sapiens population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
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220 ng/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/24273151/ |
80 mg/m² 1 times / day multiple, oral dose: 80 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered: |
CICLOPIROX plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
750 ng × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/24273151/ |
80 mg/m² 1 times / day multiple, oral dose: 80 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered: |
CICLOPIROX plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.7 h |
9 mg single, topical dose: 9 mg route of administration: Topical experiment type: SINGLE co-administered: |
CICLOPIROX unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
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2.7 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/24273151/ |
80 mg/m² 1 times / day multiple, oral dose: 80 mg/m² route of administration: Oral experiment type: MULTIPLE co-administered: |
CICLOPIROX plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
8 % 1 times / day multiple, topical Recommended Dose: 8 %, 1 times / day Route: topical Route: multiple Dose: 8 %, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Creatine phosphokinase increased... AEs leading to discontinuation/dose reduction: Creatine phosphokinase increased (0.36%) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Creatine phosphokinase increased | 0.36% Disc. AE |
8 % 1 times / day multiple, topical Recommended Dose: 8 %, 1 times / day Route: topical Route: multiple Dose: 8 %, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 >500 uM] |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/21158687/ |
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Sources: https://pubmed.ncbi.nlm.nih.gov/21158687/ |
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PubMed
Title | Date | PubMed |
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Usefulness of histological examination for the diagnosis of onychomycosis. | 2001 |
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A multicenter, open-label study of the efficacy and safety of ciclopirox nail lacquer solution 8% for the treatment of onychomycosis in patients with diabetes. | 2001 Aug |
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Ciclopirox nail lacquer: a brush with onychomycosis. | 2001 Aug |
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Role of oral antifungal agents for the treatment of superficial fungal infections in immunocompromised patients. | 2001 Jul |
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[Treatment of therapy refractory verrucae vulgares with a ciclopirox-containing lacquer]. | 2001 Jun |
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Allergic contact dermatitis from ciclopirox olamine. | 2001 May |
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[Batrafen in the treatment of fungal diseases of the skin and nails]. | 2002 Aug |
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Ciclopiroxolamine cream for treating seborrheic dermatitis: a double-blind parallel group comparison. | 2002 Dec |
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A randomised, single-blind, single-centre clinical trial to evaluate comparative clinical efficacy of shampoos containing ciclopirox olamine (1.5%) and salicylic acid (3%), or ketoconazole (2%, Nizoral) for the treatment of dandruff/seborrhoeic dermatitis. | 2002 Jun |
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Treatment of dermatophyte toenail onychomycosis in the United States. A pharmacoeconomic analysis. | 2002 May |
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Randomized, open-labeled, non-inferiority study between ciclopiroxolamine 1% cream and ketoconazole 2% foaming gel in mild to moderate facial seborrheic dermatitis. | 2003 |
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Ciclopirox olamine: head to foot. | 2003 Jan |
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Permeation of ciclopirox across porcine hoof membrane: effect of pressure sensitive adhesives and vehicles. | 2003 Nov |
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Ciclopirox gel in the treatment of patients with interdigital tinea pedis. | 2003 Sep |
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Ciclopirox gel for seborrheic dermatitis of the scalp. | 2003 Sep |
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Evaluation of the drug treatment and persistence of onychomycosis. | 2004 Aug 31 |
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Onychomycosis: review of recurrence rates, poor prognostic factors, and strategies to prevent disease recurrence. | 2004 Jul |
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Management of onychomycosis: examining the role of monotherapy and dual, triple, or quadruple therapies. | 2004 Jul |
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Safety and efficacy of ciclopirox 1% shampoo for the treatment of seborrheic dermatitis of the scalp in the US population: results of a double-blind, vehicle-controlled trial. | 2004 Jul |
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Rationale of frequency of use of ciclopirox 1% shampoo in the treatment of seborrheic dermatitis: results of a double-blind, placebo-controlled study comparing the efficacy of once, twice, and three times weekly usage. | 2004 Jul |
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Efficacy of different concentrations of ciclopirox shampoo for the treatment of seborrheic dermatitis of the scalp: results of a randomized, double-blind, vehicle-controlled trial. | 2004 Jul |
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Ciclopirox: a broad-spectrum antifungal with antibacterial and anti-inflammatory properties. | 2004 Jul |
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Eukaryotic initiation factor 5A-1 (eIF5A-1) as a diagnostic marker for aberrant proliferation in intraepithelial neoplasia of the vulva. | 2004 Jul |
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Tinea capitis favosa in Poland. | 2004 Jun |
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Agar sublimation test for the in vitro determination of the antifungal activity of morpholine derivatives. | 2004 Jun |
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Ciclopirox shampoo for treating seborrheic dermatitis. | 2004 Jun-Jul |
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[Chronic favus caused by infection with Trichophyton schönleinii]. | 2004 Oct |
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Pharmacotherapy of onychomycosis. | 2005 Apr |
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Physicochemical studies on Ciclopirox olamine complexes with divalent metal ions. | 2005 Jan 31 |
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Evaluation of the efficacy of ciclopirox 0.77% gel in the treatment of tinea pedis interdigitalis (dermatophytosis complex) in a randomized, double-blind, placebo-controlled trial. | 2005 Jul |
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In vitro susceptibility of 15 strains of zygomycetes to nine antifungal agents as determined by the NCCLS M38-A microdilution method. | 2005 Jul |
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Ciclopirox topical solution, 8% combined with oral terbinafine to treat onychomycosis: a randomized, evaluator-blinded study. | 2005 Jul-Aug |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Ciclopirox protects mitochondria from hydrogen peroxide toxicity. | 2005 Jun |
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The safety and efficacy of ciclopirox olamine for the treatment of seborrheic dermatitis. | 2005 Mar |
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Genome-wide expression profiling of the response to ciclopirox olamine in Candida albicans. | 2005 May |
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Oxygen accessibility and iron levels are critical factors for the antifungal action of ciclopirox against Candida albicans. | 2005 May |
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Ciclopirox nail lacquer 8% for the treatment of onychomycosis: a Canadian perspective. | 2005 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21022s004lbl.pdf
Seborrheic dermatitis: Wet hair and apply approximately 1 teaspoon (5 mL) of LOPROX Shampoo to the scalp. Up to 2 teaspoons (10 mL) may be used for long hair. Lather and leave on hair and scalp for 3 minutes. Rinse off. Treatment should be repeated twice per week for 4 weeks, with a minimum of 3 days between application. Onychomycosis:
Route of Administration:
Topical
Substance Class |
Chemical
Created
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Record UNII |
19W019ZDRJ
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Record Status |
Validated (UNII)
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FDA ORPHAN DRUG |
629718
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WHO-VATC |
QG01AX12
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WHO-VATC |
QD01AE14
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WHO-ATC |
G01AX12
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NDF-RT |
N0000008841
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NDF-RT |
N0000008853
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NDF-RT |
N0000000150
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NCI_THESAURUS |
C514
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WHO-ATC |
D01AE14
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NDF-RT |
N0000008577
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NDF-RT |
N0000008841
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EU-Orphan Drug |
EU/3/17/1960
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21090
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249-577-2
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29342-05-0
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CHEMBL1413
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19W019ZDRJ
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m3539
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CICLOPIROX
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453011
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C011585
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C61677
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EE-51
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Ciclopirox
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100000081889
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1134018
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SUB06245MIG
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DB01188
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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