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 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 |
---|---|---|---|---|
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 |
|
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 |
|
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 |
---|---|---|---|
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 |
---|---|---|
Role of oral antifungal agents for the treatment of superficial fungal infections in immunocompromised patients. | 2001 Jul |
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[Mode of action of ciclopiroxolamine on Candida albicans]. | 2002 |
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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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The antifungal drug ciclopirox inhibits deoxyhypusine and proline hydroxylation, endothelial cell growth and angiogenesis in vitro. | 2002 Aug 1 |
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Homologous recombination induced by replication inhibition, is stimulated by expression of mutant p53. | 2002 Jan 17 |
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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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Treatment of dermatophyte toenail onychomycosis in the United States. A pharmacoeconomic analysis. | 2002 May |
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Ciclopirox prevents peroxynitrite toxicity in astrocytes by maintaining their mitochondrial function: a novel mechanism for cytoprotection by ciclopirox. | 2002 Sep |
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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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Polarographic determination of ciclopirox olamine in pure substance and in different pharmaceutical preparations. | 2003 Dec |
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Effects of hypoxia and intracellular iron chelation on hypoxia-inducible factor-1alpha and -1beta in the rat carotid body and glomus cells. | 2003 Nov |
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Ciclopirox gel in the treatment of patients with interdigital tinea pedis. | 2003 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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Fungus-free versus disease-free nails. | 2004 Jan |
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Ciclopirox: a broad-spectrum antifungal with antibacterial and anti-inflammatory properties. | 2004 Jul |
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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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The use of 40% urea cream in the treatment of moccasin tinea pedis. | 2004 May |
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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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Treatment and prophylaxis of seborrheic dermatitis of the scalp with antipityrosporal 1% ciclopirox shampoo. | 2005 Jan |
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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 |
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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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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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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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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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C514
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CONSTITUENT ALWAYS PRESENT -> PARENT |
ASSAY (TITRATION)
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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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IMPURITY -> PARENT |
at 220 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
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