化工社化工社 化学情報印刷レポート · 研究参考用
シクロピロクス
6-シクロヘキシル-1-ヒドロキシ-4-メチル-2(1H)-ピリジノン · シクロピロックス · 6-シクロヘキシル-1-ヒドロキシ-4-メチルピリジン-2(1H)-オン · 6-シクロヘキシル-1-ヒドロキシ-4-メチル-2(1H)-ピリドン · 1-ヒドロキシ-4-メチル-6-シクロヘキシル-2(1H)-ピリドン · 6-シクロヘキシル-1-ヒドロキシ-4-メチル-1,2-ジヒドロピリジン-2-オン · シクロピロクス · 6-Cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one
識別子と物理属性
| CAS No. | 29342-05-0 |
|---|---|
| 分子式 | C12H17NO2 |
| 平均分子量 | 207.27 g/mol |
| 単同位体質量 | 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 |
| 現地名 | シクロピロクス |
化学・物理的性質
| XLogP | 2 |
|---|---|
| 極性表面積 | 40.5 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 15 |
| 形式電荷 | 0 |
| 複雑度 | 325 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| LogP（分配係数） | 2.3 |
| 溶解度 | 1.41e+00 g/L水に溶けにくく、無水エタノール、塩化メチレンに溶けやすい |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntifungal AgentsFDA approved drugs -> Active ingredient |
| 融点 | 144 °C1440C |
| Physical Description | Solid |
| 沸点 | 350.0±25.0 °C(Predicted) |
| 密度 | 1.193±0.06 g/cm3(Predicted) |
| 貯蔵条件 | Keep in dark place,Sealed in dry,Room Temperature |
| pKa（酸解離定数） | 6.25±0.58(Predicted) |
| 外観・状態 | 個体 |
| 色 | オフホワイト |
| 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 データベース | 29342-05-0(CAS DataBase Reference) |
化学的特性
White or Light-Yellow Powder
安全性と法規制
| GHS 分類 | 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%) |
| 暴露経路 | 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. |
| 毒性の概要 | 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 |
| Effects During Pregnancy and Lactation |
用途
使用
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