Luliconazole
(R,E)-2-(4-(2,4-DICHLOROPHENYL)-1,3-DITHIOLAN-2-YLIDENE)-2-(1H-IMIDAZOL-1-YL)ACETONITRILE · C13478 · PR2699 · NND 502 · Lulicon · PR 2699 · PR-2699 · Luliconazole
식별자 및 물리적 특성
| CAS No. | 187164-19-8 |
|---|---|
| 분자식 | C14H9Cl2N3S2 |
| 평균 분자량 | 354.3 g/mol |
| 단동위원소 질량 | 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 |
화학 및 물리적 성질
| XLogP | 4 |
|---|---|
| 극성 표면적 | 92.2 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 21 |
| 형식 전하 | 0 |
| 복잡도 | 476 |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| Human Drugs | Breast FeedingLactationAntifungal AgentsAnti-Infective AgentsFDA approved drugs -> Active ingredient |
| 녹는점 | 152 °C |
| 끓는 점 | 499.1±55.0 °C(Predicted) |
| 밀도 | 1.52±0.1 g/cm3(Predicted) |
| 저장 조건 | Sealed in dry,Store in freezer, under -20°C |
| 용해도 | 클로로포름(약간 용해됨), 에틸아세테이트(약간 용해됨) |
| 물리적 상태 | 고체 |
| pKa(산도 계수) | 3.76±0.10(Predicted) |
| 색상 | 흰색에서 황백색까지 |
| 안정성 | 감광성 |
| 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| |
안전 및 규제
| GHS 분류 | 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 |
| 수질 위해 등급(WGK) | WGK 3 |
| 관세 코드 | 2933.29.2000 |
| 위험 등급 | Eye Irrit. 2Skin Irrit. 2 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
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. .
용도
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.