Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H17NO2.C2H7NO |
Molecular Weight | 268.352 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCO.CC1=CC(=O)N(O)C(=C1)C2CCCCC2
InChI
InChIKey=MBRHNTMUYWQHMR-UHFFFAOYSA-N
InChI=1S/C12H17NO2.C2H7NO/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10;3-1-2-4/h7-8,10,15H,2-6H2,1H3;4H,1-3H2
Molecular Formula | C2H7NO |
Molecular Weight | 61.0831 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|---|
Target ID: CHEMBL2366381 |
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Target ID: CHEMBL2363058 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
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 |
---|---|---|---|---|
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 |
---|---|---|
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 |
---|---|---|---|
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 |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
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 |
---|---|---|
Evaluation of in vitro resistance in patients with onychomycosis who fail antifungal therapy. | 2003 |
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Successful treatment of dandruff with 1.5% ciclopirox olamine shampoo in Korea. | 2003 Dec |
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Action mechanisms of modern antifungal agents and resulting problems in the management of onychomycosis. | 2003 Dec |
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A randomized comparison of nail surface remanence of three nail lacquers, containing amorolfine 5%, ciclopirox 8% or tioconazole 28%, in healthy volunteers. | 2004 |
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Assessing treatment outcomes in toenail onychomycosis clinical trials. | 2004 |
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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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Evaluation of the drug treatment and persistence of onychomycosis. | 2004 Aug 31 |
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Ciclopirox (Loprox) gel for superficial fungal infections. | 2004 Aug-Sep |
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[Onychomycosis]. | 2004 Feb |
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Managing simple chronic paronychia and onycholysis with ciclopirox 0.77% and an irritant-avoidance regimen. | 2004 Jan |
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Dermacase. Pityriasis rosea. | 2004 Jan |
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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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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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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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The use of 40% urea cream in the treatment of moccasin tinea pedis. | 2004 May |
|
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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Management of onychomycosis with topicals. | 2004 Oct |
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Ciclopirox delivery into the human nail plate. | 2004 Oct |
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Cell cycle arrest at the initiation step of human chromosomal DNA replication causes DNA damage. | 2004 Oct 1 |
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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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Pharmacoeconomic analysis of sequential treatment pathways in the treatment of onychomycosis. | 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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Topical antifungal drugs for the treatment of onychomycosis: an overview of current strategies for monotherapy and combination therapy. | 2005 Jan |
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Physicochemical studies on Ciclopirox olamine complexes with divalent metal ions. | 2005 Jan 31 |
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A multicenter, open-label study to assess the safety and efficacy of ciclopirox topical suspension 0.77% in the treatment of diaper dermatitis due to Candida albicans. | 2005 Jan-Feb |
|
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 |
|
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 |
|
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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Trichophyton rubrum isolated from aids and human immunodeficiency virus-infected patients in São Paulo, Brazil: antifungal susceptibility and extracellular enzyme production. | 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
by
admin
on
Edited
Wed Jul 05 22:47:08 UTC 2023
by
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on
Wed Jul 05 22:47:08 UTC 2023
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Record UNII |
50MD4SB4AP
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Record Status |
Validated (UNII)
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C514
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CONSTITUENT ALWAYS PRESENT -> PARENT |
ASSAY (TITRATION)
EP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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PARENT -> SALT/SOLVATE |
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PARENT -> SALT/SOLVATE |
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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 |
at 220 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
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