基本情報
- CAS
182760-06-1- 標準SMILES
C[C@@H](c1nc(-c2ccc(C#N)cc2)cs1)[C@](O)(Cn1cncn1)c1ccc(F)cc1F- InChIKey
OPAHEYNNJWPQPX-RCDICMHDSA-N- 分子式
- C22H17F2N5OS
- 平均分子量
- 437.5 g/mol
- 単同位体質量
- 437.1121876
概要
Ravuconazole is a member of the class of triazoles that is 1-butyl-1H-1,2,4-triazole in which the butyl group is substituted at positions 2, 2, and 3 by hydroxy, 2,4-difluorophenyl, and 4-(p-cyanophenyl)-1,3-thiazol-2-yl groups, respectively (the R,R stereoisomer). It exhibits antifungal activity by inhibition of 14alpha demethylase, an enzyme involved in sterol synthesis, resulting in lysis of the fungal cell wall and fungal cell death. (NCIO4). It has a role as an EC 1.14.14.154 (sterol 14alpha-demethylase) inhibitor, an antileishmanial agent, an ergosterol biosynthesis inhibitor and an antifungal drug. It is a nitrile, a tertiary alcohol, a member of fluorobenzenes, a member of triazoles and a member of 1,3-thiazoles.
名称と識別子
- 優先名称
- Ravuconazole
- IUPAC
- 4-[2-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl]benzonitrile
- 現地名
- ラブコナゾール
- 英語名
- Ravuconazole
- 分子式
- C22H17F2N5OS
- 分子量
- 437.47
名称と別名
Ravuconazole182760-06-1ER-30346BMS-207147ER 30346BMS 20714795YH599JWVBenzonitrile, 4-[2-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]-4-{2-[(2r,3r)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1h-1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl}benzonitrileCHEBI:143825DTXSID40171329p-(2-((alphaR,betaR)-2,4-Difluoro-beta-hydroxy-alpha-methyl-beta-(1H-1,2,4-triazol-1-ylmethyl)phenethyl)-4-thiazolyl)benzonitrile
名称をさらに表示
ラブコナゾール4-[2-[(1R,2R)-3-(1H-1,2,4-トリアゾール-1-イル)-1-メチル-2-ヒドロキシ-2-(2,4-ジフルオロフェニル)プロピル]チアゾール-4-イル]ベンゾニトリル4-{2-[(2R,3R)-3-(2,4-ジフルオロフェニル)-3-ヒドロキシ-4-(1H-1,2,4-トリアゾール-1-イル)ブタン-2-イル]-1,3-チアゾール-4-イル}ベンゾニトリル4-[2-[(1R,2R)-2-(2,4-ジフルオロフェニル)-2-ヒドロキシ-1-メチル-3-(1H-1,2,4-トリアゾール-1-イル)プロピル]チアゾール-4-イル]ベンゾニトリル4-[2-[(1R,2R)-1-メチル-2-ヒドロキシ-2-(2,4-ジフルオロフェニル)-3-(1H-1,2,4-トリアゾール-1-イル)プロピル]チアゾール-4-イル]ベンゾニトリルRczAids057176The healthBms-207,147
物性
構造計算による物性
- XLogP
- 3.5
- 極性表面積
- 116 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 8
- 回転可能結合数
- 6
- 重原子数
- 31
- 形式電荷
- 0
- 複雑度
- 657
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
PesticidesFungicides
物理化学的性質
- 融点
- 64 · 64-66°C
- 比旋光度
- 24 · D24 -29.1° (c = 1.03 in methanol)
- 沸点
- 674.9 · 674.9±65.0 °C(Predicted)
- 比重(密度)
- 1.38 · 1.38±0.1 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · -20°C Freezer
- 溶解性
- 25 mg/ml; · DMF: 25 mg/ml; DMF:PBS (pH 7.2) (1:4): 0.25 mg/ml; DMSO: 20 mg/ml; Ethanol: 5 mg/ml
- 外見
- A crystalline solid
- 酸解離定数(Pka)
- 11.62 · 11.62±0.29(Predicted)
- 色
- Off-white to yellow
- InChI
- InChI=1S/C22H17F2N5OS/c1-14(21-28-20(10-31-21)16-4-2-15(9-25)3-5-16)22(30,11-29-13-26-12-27-29)18-7-6-17(23)8-19(18)24/h2-8,10,12-14,30H,11H2,1H3/t14-,22+/m0/s1
- InChIKey
- OPAHEYNNJWPQPX-RCDICMHDSA-N
- SMILES
- C(#N)C1=CC=C(C2=CSC([C@H](C)[C@](C3=CC=C(F)C=C3F)(O)CN3C=NC=N3)=N2)C=C1
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
危険有害性情報
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
安全データ
- wgk
- WGK 3
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
用途と製造
Use ClassificationFungicides
応用分野
説明Ravuconazole is an orally available triazole fungicide that potently inhibits the growth of a wide range of fungi (MICs range from 25 to 780 ng/ml). Like other azoles, ravuconazole inhibits cytochrome P450 (CYP) isoforms that are involved in ergosterol biosynthesis, interfering with the generation of the fungal and protozoan cell membranes. Ravuconazole specifically inhibits sterol 14α-demethylase (CYP51). As this enzyme is also important in the development of trypanosomes, ravuconazole is effective against T. cruzi infections in animal models of Chagas disease.
使用Ergosterol biosynthesis inhibitor. Antifungal.
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