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Ciclopirox
6-Cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one · Penlac · gopmx · geprox · Loprox · HOE296b · Mycoster · Brumixol
Identifikatoren & physikalische Daten
| CAS No. | 29342-05-0 |
|---|---|
| Summenformel | C12H17NO2 |
| Durchschnittliche Molmasse | 207,27 g/mol |
| Monoisotopische Masse | 207,12592879 g/mol |
| SMILES | Cc1cc(C2CCCCC2)n(O)c(=O)c1 |
| InChIKey | SCKYRAXSEDYPSA-UHFFFAOYSA-N |
| PubChem CID | 2749 |
| ChEMBL | CHEMBL1413 |
| ChEBI | CHEBI:453011 |
| EC No. | 249-577-2 |
| DTXSID | DTXSID9048564 |
| Lokaler Name | Ciclopirox |
Chemische & physikalische Eigenschaften
| XLogP | 2 |
|---|---|
| Polarare Oberfläche (TPSA) | 40,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 325 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| LogP (Verteilungskoeffizient) | 2.3 |
| Löslichkeit | 1.41e+00 g/LSlightly soluble in water, freely soluble in anhydrous ethanol and in methylene chloride |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntifungal AgentsFDA approved drugs -> Active ingredient |
| Schmelzpunkt | 144 °C1440C |
| Physical Description | Solid |
| Siedepunkt | 350.0±25.0 °C(Predicted) |
| Dichte | 1.193±0.06 g/cm3(Predicted) |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| pKa (Säurekonstante) | 6.25±0.58(Predicted) |
| Aggregatzustand | Solid |
| Farbe | Off-White |
| InChI | 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 |
| InChIKey | SCKYRAXSEDYPSA-UHFFFAOYSA-N |
| SMILES | C1(=O)N(O)C(C2CCCCC2)=CC(C)=C1 |
| CAS Datenbank | 29342-05-0(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.1% (1 of 89) of reports.WarningH302+H312+H332 (32.6%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P321, P330, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 89 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (93.3%) |
| Expositionspfade | 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. |
| Toxizitätsübersicht | 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. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)ciclopiroxDILI NegativeTopicalDOI:10.1016/j.drudis.2019.09.022 |
Anwendungen & Verwendung
Verwenden
Ciclopirox (Penlac) is a synthetic antifungal agent. Ciclopirox (Penlac) is used for topical dermatologic treatment of superficial mycoses. Ciclopirox (Penlac) is most useful against Tinea versicolor. [1] In a study conducted to further elucidate ciclopir