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 |
|
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 Date4.10054394E11 |
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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 Date9.4530241E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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25.02 ng/mL |
5 g single, topical dose: 5 g route of administration: Topical experiment type: SINGLE co-administered: |
CICLOPIROX blood | Homo sapiens population: HEALTHY age: UNKNOWN sex: 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 |
Doses
Dose | Population | Adverse events |
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8 % 1 times / day multiple, topical Recommended Dose: 8 %, 1 times / day Route: topical Route: multiple Dose: 8 %, 1 times / day Sources: Page: p.11 |
unhealthy n = 281 Health Status: unhealthy Condition: Onychomycosis Population Size: 281 Sources: Page: p.11 |
Disc. AE: Creatine phosphokinase increased... AEs leading to discontinuation/dose reduction: Creatine phosphokinase increased (0.36%) Sources: Page: p.11 |
AEs
AE | Significance | Dose | Population |
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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: Page: p.11 |
unhealthy n = 281 Health Status: unhealthy Condition: Onychomycosis Population Size: 281 Sources: Page: p.11 |
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 |
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no [IC50 >500 uM] |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
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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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Anatomy of the primase-alpha DNA polymerase reaction accomplished by nucleoprotein complexes harboring an extrachromosomal DNA identical with avian myeloblastosis virus core-bound DNA: influencing by carbonyldiphosphonate, mimosine and butylphenyl deoxyguanosine-5'-triphosphate. | 2001 Apr |
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Successful treatment of onychomycosis with ciclopirox nail lacquer: a case report. | 2001 Aug |
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Six novel antimycotics. | 2002 |
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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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[Tinea]. | 2002 Jul |
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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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Extra- and intracellular free iron and the carotid body responses. | 2002 Mar |
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Treatment of dermatophyte toenail onychomycosis in the United States. A pharmacoeconomic analysis. | 2002 May |
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Ciclopiroxolamine: in vitro antifungal activity against clinical yeast isolates. | 2002 Nov |
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[Therapy problems in chronic recurrent vaginal mycosis]. | 2002 Sep |
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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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In vitro susceptibility testing of ciclopirox, terbinafine, ketoconazole and itraconazole against dermatophytes and nondermatophytes, and in vitro evaluation of combination antifungal activity. | 2003 Aug |
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Ciclopirox olamine: head to foot. | 2003 Jan |
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Onychomycosis in children: an overview. | 2003 Jan |
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Dermatophyte infections. | 2003 Jan 1 |
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Anodic polarographic determination of ciclopirox olamine in pure and certain pharmaceutical preparations. | 2003 Jun 1 |
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Economic analysis of oral and topical therapies for onychomycosis of the toenails and fingernails. | 2003 Mar |
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Topical treatments for onychomycosis: a historical perspective. | 2003 Mar-Apr |
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Treatment of onychomycosis in the diabetic patient population. | 2003 Mar-Apr |
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Permeation of ciclopirox across porcine hoof membrane: effect of pressure sensitive adhesives and vehicles. | 2003 Nov |
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Deep mycosis caused by Trichophyton mentagrophytes in a diabetic patient. | 2003 Sep |
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Ciclopirox gel for seborrheic dermatitis of the scalp. | 2003 Sep |
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Evaluation of in vitro activity of ciclopirox olamine, butenafine HCl and econazole nitrate against dermatophytes, yeasts and bacteria. | 2003 Sep |
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Ciclopirox gel: an update. | 2003 Sep |
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Common fungal infections of the feet in patients with diabetes mellitus. | 2004 |
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In vitro susceptibility testing of dermatophytes: comparison of disk diffusion and reference broth dilution methods. | 2004 Apr |
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[Onychomycosis]. | 2004 Feb |
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Fungus-free versus disease-free nails. | 2004 Jan |
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Treatment of onychomycosis: pros and cons of antifungal agents. | 2004 Jan-Feb |
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Onychomycosis in children: a brief overview with treatment strategies. | 2004 Jan-Feb |
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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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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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Agar sublimation test for the in vitro determination of the antifungal activity of morpholine derivatives. | 2004 Jun |
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Activation of HIF-1alpha mRNA by hypoxia and iron chelator in isolated rat carotid body. | 2004 Jun 17 |
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Ciclopirox shampoo for treating seborrheic dermatitis. | 2004 Jun-Jul |
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Cutaneous adiaspiromycosis: a distinct dermatologic entity associated with Chrysosporium species. | 2004 Nov |
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[Chronic favus caused by infection with Trichophyton schönleinii]. | 2004 Oct |
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Ciclopirox delivery into the human nail plate. | 2004 Oct |
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Pharmacotherapy of onychomycosis. | 2005 Apr |
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In vitro transungual permeation of ciclopirox from a hydroxypropyl chitosan-based, water-soluble nail lacquer. | 2005 Jan |
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Treatment and prophylaxis of seborrheic dermatitis of the scalp with antipityrosporal 1% ciclopirox shampoo. | 2005 Jan |
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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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Copper-dependent activation of hypoxia-inducible factor (HIF)-1: implications for ceruloplasmin regulation. | 2005 Jun 15 |
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The safety and efficacy of ciclopirox olamine for the treatment of seborrheic dermatitis. | 2005 Mar |
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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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admin
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Wed Jul 05 23:19:48 UTC 2023
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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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N0000008853
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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 |
Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
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 |