3054 Ciclopirox Ciclopirox is only found in individuals that have used or taken this drug. It is a synthetic antifungal agent for topical dermatologic use. [Wikipedia] 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 Fe³⁺ and Al³⁺. 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. 29342-05-0 2749 C12H17NO2 207.125930 White powder. 143°C 1.41e+00 g/L 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. 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 Fe³⁺ and Al³⁺. 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. Glucuronidation is the main metabolic pathway of ciclopirox. Route of Elimination: 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. Half Life: 1.7 hours for 1% topical solution. LD50: >10 ml/kg (Oral, Rat) (A308) No indication of carcinogenicity to humans (not listed by IARC). 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>. 2009-07-21T20:28:34Z 2026-03-31T18:35:19Z Ciclopirox 453011 Ciclopirox DB01188 true CC1=CC(=O)N(O)C(=C1)C1CCCCC1 C12H17NO2 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 SCKYRAXSEDYPSA-UHFFFAOYSA-N 207.2689 207.125928793 Exogenous Solid 2.3 HMDB15319 CHEMBL1413 2647 <p>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.</p> CHEM002369 DTXSID9048564 NS00010120 6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one