ルリコナゾール
ルリコナゾール · (2E)-2-[(4R)-4-(2,4-ジクロロフェニル)-1,3-ジチオラン-2-イリデン]-2-(1H-イミダゾール-1-イル)アセトニトリル · ルリコナゾール (JAN) · (-)-(E)-[(4R)-4-(2,4-ジクロロフェニル)-1,3-ジチオラン-2-イリデン](イミダゾール-1-イル)アセトニトリル · [(2E,4R)-4-(2,4-ジクロロフェニル)-1,3-ジチオラン-2-イリデン](1H-イミダゾール-1-イル)アセトニトリル · ルリコン · 2-[(2E,4R)-4-(2,4-ジクロロフェニル)-1,3-ジチオラン-2-イリデン]-2-(1H-イミダゾール-1-イル)アセトニトリル · 2-(1H-イミダゾール-1-イル)-2-[(E)-4α-(2,4-ジクロロフェニル)-1,3-ジチオラン-2-イリデン]アセトニトリル
識別子と物理属性
| CAS No. | 187164-19-8 |
|---|---|
| 分子式 | C14H9Cl2N3S2 |
| 平均分子量 | 354.3 g/mol |
| 単同位体質量 | 352.961495 g/mol |
| SMILES | N#C/C(=C1/SC[C@@H](c2ccc(Cl)cc2Cl)S1)n1ccnc1 |
| InChIKey | YTAOBBFIOAEMLL-REQDGWNSSA-N |
| PubChem CID | 3003141 |
| ChEMBL | CHEMBL2105689 |
| ChEBI | CHEBI:34825 |
| EC No. | 878-713-9 |
| DTXSID | DTXSID3048607 |
| 現地名 | ルリコナゾール |
化学・物理的性質
| XLogP | 4 |
|---|---|
| 極性表面積 | 92.2 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 2 |
| 重原子数 | 21 |
| 形式電荷 | 0 |
| 複雑度 | 476 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| Human Drugs | Breast FeedingLactationAntifungal AgentsAnti-Infective AgentsFDA approved drugs -> Active ingredient |
| 融点 | 152 °C |
| 沸点 | 499.1±55.0 °C(Predicted) |
| 密度 | 1.52±0.1 g/cm3(Predicted) |
| 貯蔵条件 | Sealed in dry,Store in freezer, under -20°C |
| 溶解度 | クロロホルム（微量）、酢酸エチル（微量） |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | 3.76±0.10(Predicted) |
| 色 | ホワイトからオフホワイト |
| 安定性 | 光に敏感 |
| InChI | InChI=1/C14H9Cl2N3S2/c15-9-1-2-10(11(16)5-9)13-7-20-14(21-13)12(6-17)19-4-3-18-8-19/h1-5,8,13H,7H2/b14-12+/t13-/s3 |
| InChIKey | YTAOBBFIOAEMLL-YZDXEGGZNA-N |
| SMILES | ClC1C=C(Cl)C=CC=1[C@@H]1CS/C(=C(\N2C=NC=C2)/C#N)/S1 |&1:8,r| |
| CAS データベース | 187164-19-8 |
安全性と法規制
| GHS 分類 | WarningH302 (66.7%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (66.7%) |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| 水環境危害等級（WGK） | WGK 3 |
| 税関コード | 2933.29.2000 |
| 危険等級 | Eye Irrit. 2Skin Irrit. 2 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
説明
Luliconazole is a member of the imidazole class of antifungal agents, with specific utility as a dermatological antimycotic drug. It was launched in Japan as a topical agent for the treatment of athlete’s foot. Luliconazole is an optically active drug with (R)-configuration at its chiral center. It is structurally related to lanoconazole, which has been marketed as a racemic mixture since 1994. As with other azole antifungal drugs, the mechanism of action of luliconazole is the inhibition of sterol 14-a-demethylase, and subsequently, inhibition of ergosterol biosynthesis. The in vivo activity of luliconazole against dermatophytes has been evaluated in the guinea pig model of tinea pedis. In this study, a 1% topical solution of luliconazole, administered once daily for seven days, achieved complete mycologic cure. Additionally, there were no occurrences of relapse for up to 16 weeks after the treatment. No data is currently available on the clinical efficacy of luliconazole. The chemical synthesis of luliconazole involves the condensation of 1-(cyanomethyl)imidazole with carbon disulfide to produce a dithioate intermediate, and subsequent alkylation with either the mesylate derivative of (S′)-1-(2,4-dichlorophenyl)-2-bromoethanol or the bis-mesylate derivative of (S′)-1-(2,4-dichlorophenyl)ethane-1,2-diol. .
使用
Luliconazole is an azole antifungal drug. It was approved by the FDA (USA) in November 2013 and is marketed under the brand name Luzu. Luliconazole is also approved in Japan.