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Namespace Prefixes

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Statements

Subject Item
n2:DB01188
rdf:type
n3:Drug
n3:description
Ciclopirox 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]
n3:dosage
n4:271B514E-363D-11E5-9242-09173F13E4C5 n4:271B514F-363D-11E5-9242-09173F13E4C5 n4:271B5150-363D-11E5-9242-09173F13E4C5 n4:271B5151-363D-11E5-9242-09173F13E4C5 n4:271B5152-363D-11E5-9242-09173F13E4C5 n4:271B5153-363D-11E5-9242-09173F13E4C5 n4:271B5154-363D-11E5-9242-09173F13E4C5 n4:271B5155-363D-11E5-9242-09173F13E4C5 n4:271B5156-363D-11E5-9242-09173F13E4C5 n4:271B5157-363D-11E5-9242-09173F13E4C5 n4:271B514D-363D-11E5-9242-09173F13E4C5 n4:271B514B-363D-11E5-9242-09173F13E4C5 n4:271B514C-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# 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":http://www.ncbi.nlm.nih.gov/pubmed/12760852 # 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":http://www.ncbi.nlm.nih.gov/pubmed/15790671
n3:group
approved investigational
n3:halfLife
1.7 hours for 1% topical solution.
n3:indication
Used as a topical treatment in immunocompetent patients with mild to moderate onychomycosis of fingernails and toenails without lunula involvement, due to <i>Trichophyton rubrum</i>.
owl:sameAs
n7:DB01188 n24:DB01188
dcterms:title
Ciclopirox
adms:identifier
n13:50231223 n14:2647 n15:46506333 n17:2749 n18:D01364 n19:0066-8008-01 n20:DB01188 n21:PA164747060 n22:Ciclopirox n23:453011
n3:mechanismOfAction
Unlike antifungals such as itraconazole and terbinafine, which affect sterol synthesis, ciclopirox is thought to act through the chelation of polyvalent metal cations, such as Fe<sup>3+</sup> and Al<sup>3+</sup>. 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.
n3:packager
n11:271B5115-363D-11E5-9242-09173F13E4C5 n11:271B5116-363D-11E5-9242-09173F13E4C5 n11:271B5119-363D-11E5-9242-09173F13E4C5 n11:271B511A-363D-11E5-9242-09173F13E4C5 n11:271B5117-363D-11E5-9242-09173F13E4C5 n11:271B5118-363D-11E5-9242-09173F13E4C5 n11:271B512F-363D-11E5-9242-09173F13E4C5 n11:271B5130-363D-11E5-9242-09173F13E4C5 n11:271B512D-363D-11E5-9242-09173F13E4C5 n11:271B512E-363D-11E5-9242-09173F13E4C5 n11:271B5133-363D-11E5-9242-09173F13E4C5 n11:271B5131-363D-11E5-9242-09173F13E4C5 n11:271B5132-363D-11E5-9242-09173F13E4C5 n11:271B5127-363D-11E5-9242-09173F13E4C5 n11:271B5128-363D-11E5-9242-09173F13E4C5 n11:271B511D-363D-11E5-9242-09173F13E4C5 n11:271B5125-363D-11E5-9242-09173F13E4C5 n11:271B511E-363D-11E5-9242-09173F13E4C5 n11:271B5126-363D-11E5-9242-09173F13E4C5 n11:271B511B-363D-11E5-9242-09173F13E4C5 n11:271B512B-363D-11E5-9242-09173F13E4C5 n11:271B511C-363D-11E5-9242-09173F13E4C5 n11:271B512C-363D-11E5-9242-09173F13E4C5 n11:271B5129-363D-11E5-9242-09173F13E4C5 n11:271B512A-363D-11E5-9242-09173F13E4C5 n11:271B511F-363D-11E5-9242-09173F13E4C5 n11:271B5120-363D-11E5-9242-09173F13E4C5 n11:271B5123-363D-11E5-9242-09173F13E4C5 n11:271B5124-363D-11E5-9242-09173F13E4C5 n11:271B5121-363D-11E5-9242-09173F13E4C5 n11:271B5122-363D-11E5-9242-09173F13E4C5
n3:patent
n16:7018656 n16:7026337
n3:routeOfElimination
Most 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.
n3:synonym
6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone Ciclopiroxum
n3:toxicity
Oral LD<sub>50</sub> in rat is >10 ml/kg. Symptoms of overexposure include drowsiness and headache.
n9:hasAHFSCode
n10:84-04-08-20
n3:proteinBinding
Protein binding is 94-97% following topical administration.
n3:synthesisReference
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.
n31:hasConcept
n32:M0057995
foaf:page
n27:lop1236.shtml n28:penlac.htm n30:ciclopirox-cream.html
n3:IUPAC-Name
n5:271B515C-363D-11E5-9242-09173F13E4C5
n3:InChI
n5:271B5162-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n5:271B5161-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n5:271B515E-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n5:271B515F-363D-11E5-9242-09173F13E4C5
n3:SMILES
n5:271B5160-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n5:271B515A-363D-11E5-9242-09173F13E4C5
n3:logP
n5:271B5158-363D-11E5-9242-09173F13E4C5 n5:271B515B-363D-11E5-9242-09173F13E4C5 n5:271B5173-363D-11E5-9242-09173F13E4C5
n3:logS
n5:271B5159-363D-11E5-9242-09173F13E4C5
n9:hasATCCode
n25:G01AX12 n25:D01AE14
n3:H-Bond-Acceptor-Count
n5:271B5168-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n5:271B5169-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n5:271B5163-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n5:271B5164-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n5:271B5166-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n5:271B5165-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n5:271B5167-363D-11E5-9242-09173F13E4C5
n3:absorption
Rapidly 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.
n3:affectedOrganism
Yeast and other fungi Humans and other mammals
n3:casRegistryNumber
29342-05-0
n3:category
n3:containedIn
n8:271B5149-363D-11E5-9242-09173F13E4C5 n8:271B513D-363D-11E5-9242-09173F13E4C5 n8:271B513E-363D-11E5-9242-09173F13E4C5 n8:271B513B-363D-11E5-9242-09173F13E4C5 n8:271B513C-363D-11E5-9242-09173F13E4C5 n8:271B5141-363D-11E5-9242-09173F13E4C5 n8:271B5142-363D-11E5-9242-09173F13E4C5 n8:271B513F-363D-11E5-9242-09173F13E4C5 n8:271B5140-363D-11E5-9242-09173F13E4C5 n8:271B5135-363D-11E5-9242-09173F13E4C5 n8:271B5136-363D-11E5-9242-09173F13E4C5 n8:271B5134-363D-11E5-9242-09173F13E4C5 n8:271B5139-363D-11E5-9242-09173F13E4C5 n8:271B513A-363D-11E5-9242-09173F13E4C5 n8:271B5137-363D-11E5-9242-09173F13E4C5 n8:271B5138-363D-11E5-9242-09173F13E4C5 n8:271B5145-363D-11E5-9242-09173F13E4C5 n8:271B5146-363D-11E5-9242-09173F13E4C5 n8:271B5143-363D-11E5-9242-09173F13E4C5 n8:271B5144-363D-11E5-9242-09173F13E4C5 n8:271B5147-363D-11E5-9242-09173F13E4C5 n8:271B5148-363D-11E5-9242-09173F13E4C5 n8:271B514A-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n5:271B516E-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n5:271B5170-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n5:271B5171-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n5:271B5172-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n5:271B516D-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n5:271B516C-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n5:271B516F-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n5:271B515D-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n5:271B516A-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n5:271B516B-363D-11E5-9242-09173F13E4C5