Bindarit

HCID 71354

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Grundinformationen

CAS: 130641-38-2
Standard-SMILES: CC(C)(OCc1nn(Cc2ccccc2)c2ccccc12)C(=O)O
InChIKey: MTHORRSSURHQPZ-UHFFFAOYSA-N
Summenformel: C19H20N2O3
Durchschnittliche Molmasse: 324,4 g/mol
Monoisotopische Masse: 324,1473925

Namen und Bezeichner

Bevorzugter Name: Bindarit
IUPAC: 2-[(1-benzylindazol-3-yl)methoxy]-2-methylpropanoic acid
Englischer Name: Bindarit
Summenformel: C19H20N2O3
Molmasse: 324.37

Namen und Synonyme

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

Weitere Namen anzeigen

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)-

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3
Polarare Oberfläche (TPSA): 64,4 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 4
Frei drehbare Bindungen: 6
Schwere Atome: 24
Formalladung: 0
Komplexität: 434

Physikochemische Eigenschaften

Siedepunkt: 542.9 · 542.9±40.0 °C(Predicted)
Dichte: 1.18 · 1.18±0.1 g/cm3 (20 ºC 760 Torr)
storage temp.: 2 · 2-8°C
Löslichkeit: 47 · DMSO:47.0(Max Conc. mg/mL);144.89(Max Conc. mM)
Aggregatzustand: A crystalline solid
pka: 3.59 · 3.59±0.10(Predicted)
Farbe: 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

Sicherheit und Regulatorisches

Sicherheitsdaten

wgk: WGK 3
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Anwendungen · 2 Einträge

BeschreibungBindarit 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.

VerwendenBindarit 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.