CAS 130641-38-2 Bindarit (HCID 71354)

基本情報

CAS: 130641-38-2
標準SMILES: CC(C)(OCc1nn(Cc2ccccc2)c2ccccc12)C(=O)O
InChIKey: MTHORRSSURHQPZ-UHFFFAOYSA-N
分子式: C19H20N2O3
平均分子量: 324.4 g/mol
単同位体質量: 324.1473925

名称と識別子

優先名称: Bindarit
IUPAC: 2-[(1-benzylindazol-3-yl)methoxy]-2-methylpropanoic acid
現地名: ビンダリット
英語名: Bindarit
分子式: C19H20N2O3
分子量: 324.37

名称と別名

Bindarit130641-38-22-((1-Benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid2-[(1-benzyl-1h-indazol-3-yl)methoxy]-2-methylpropanoic acidAF 2838AF-28382-[(1-benzylindazol-3-yl)methoxy]-2-methylpropanoic acidJQ11LH711MDTXSID301566602-((1-Benzyl-1H-indazol-3-yl)methoxy)-2-methylpropionic acidbindaritum2-((1-benzylindazol-3-yl)methoxy)-2-methylpropanoic acid

名称をさらに表示

ビンダリットビンダリト2-[(1-ベンジル-1H-インダゾール-3-イル)メトキシ]-2-メチルプロパン酸CS-1989indaritBindarit (AF2838)Bindarit, 10 mM in DMSOBindarit, CCL2, CCL7 and CCL8 inhibitor

RefChem:917198DTXCID30791512-((1-benzyl-3-indazolyl)methoxy)-2-methylpropionic acid2-((-1-benzyl-indazol-3-yl)methoxy)-2-methylpropionic acidAF2838Propanoic acid, 2-methyl-2-[[1-(phenylmethyl)-1H-indazol-3-yl]methoxy]-MFCD00866723Propanoic acid, 2-methyl-2-((1-(phenylmethyl)-1H-indazol-3-yl)methoxy)-

データベース識別子

CAS: 130641-38-2
PubChem CID: 71354
DTXSID: DTXSID30156660
ChEMBL: CHEMBL2107549
UNII: JQ11LH711M
Nikkaji: J561.826F

物性

構造計算による物性

XLogP: 3
極性表面積: 64.4 Å²
水素結合供与体数: 1
水素結合受容体数: 4
回転可能結合数: 6
重原子数: 24
形式電荷: 0
複雑度: 434

物理化学的性質

沸点: 542.9 · 542.9±40.0 °C(Predicted)
比重(密度): 1.18 · 1.18±0.1 g/cm3 (20 ºC 760 Torr)
貯蔵温度: 2 · 2-8°C
溶解性: 47 · DMSO:47.0(Max Conc. mg/mL);144.89(Max Conc. mM)
外見: A crystalline solid
酸解離定数(Pka): 3.59 · 3.59±0.10(Predicted)
色: White to off-white
InChI: InChI=1S/C19H20N2O3/c1-19(2,18(22)23)24-13-16-15-10-6-7-11-17(15)21(20-16)12-14-8-4-3-5-9-14/h3-11H,12-13H2,1-2H3,(H,22,23)
InChIKey: MTHORRSSURHQPZ-UHFFFAOYSA-N
SMILES: C(O)(=O)C(C)(OCC1C2=C(N(CC3=CC=CC=C3)N=1)C=CC=C2)C

安全と法規制

安全データ

wgk: WGK 3
ストレージクラス: 11 - Combustible Solids

化学と産業

応用分野 · 2 件

説明Bindarit is an inhibitor of monocyte chemoattractant protein (MCP) production that is selective for MCP-1/CCL2, MPC-3/CCL7, and MCP-2/CCL8 over other chemokines. It inhibits LPS- or C. albicans-induced production of MCP-1/CCL2 in isolated human monocytes (IC50s = 172 and 403 μM, respectively). Bindarit downregulates NF-κB signaling and prevents p65 and p65/p50-mediated MCP-1/CCL2 promoter activation in RAW264.7 cells. It delays the onset of proteinuria and prolongs survival in a mouse model of experimental lupus nephritis when administered at a dose of 50 mg/kg. It prevents LPS-induced increases in MCP-1/CCL2 expression in mouse brain and spinal cord when administered at a dose of 200 mg/kg and reduces the incidence and severity of experimental autoimmune encephalomyelitis (EAE) in mice. Bindarit is also a noncompetitive inhibitor of monocarboxylate transporter 4 (MCT4; Ki = 30.2 μM for the human transporter) that is selective for MCT4 over MCT1.

使用Bindarit shows anti-inflammatory activity due to a selective inhibition of a subfamily of inflammatory chemokines. Bindarit is a also protein antidenaturant agent. Bindarit modulates the NFkB pathway and has been shown to reduce secondary phase of adjuvant arthritis in rats.