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Merck
CN

SML2910

Sigma-Aldrich

Bindarit

≥98% (HPLC)

Synonym(s):

2-((1-Benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid, 2-Methyl-2-[[1-(phenylmethyl)-1H-indazol-3-yl]methoxy]propanoic acid, AF 2838, AF2838

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About This Item

Empirical Formula (Hill Notation):
C19H20N2O3
CAS Number:
130641-38-2
Molecular Weight:
324.37
MDL number:
MFCD00866723
UNSPSC Code:
51111800
NACRES:
NA.77

Key Documents

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Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

[n]2(nc(c3c2cccc3)COC(C)(C)C(=O)O)Cc1ccccc1

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)

InChI key

MTHORRSSURHQPZ-UHFFFAOYSA-N

Related Categories

Biochem/physiol Actions

Bindarit is an indazolic derivative with anti-inflammatory efficacy in vitro (150-300 μM) and in animal disease models in vivo (100 mg/kg ip, 50 mg/kg po, or 0.5% in chow; rats & mice). Bindarit selectively inhibits LPS-induced CCL2/MCP-1, CCL7/MCP-3, CCL8/MCP-2 chemokines over CCL3/MIP-1α and IL-8/CXCL8 in human monocytes, while blocking CCL2, but not CCL7 or CCL8, induction in HUVECs, and preventing LPS-induced CCL2 & IL-12β/p40 by inhibiting NFκB activation in murine macrophages (BMDM & Raw 264.7). Bindarit is also reported to exhibit non-competitive inhibiory potency against human monocarboxylate transporter MCT4 (Ki = 30.2 μM) over MCT1 (<40% inhibition at 500 μM).
NFκB activation, CCL2 (MCP1) & IL-12β/p40 induction blocker with anti-inflammation efficacy in vivo. Selectively inhibits monocarboxylate transporter MCT4 over MCT1.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000396688
0000396688
0000223830
0000223830
0000106377

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Guo-Xiong Zhou et al.
Hepatobiliary & pancreatic diseases international : HBPD INT, 9(2), 201-207 (2010-04-13)
Chemokines and their receptors play key roles in the pathogenesis of acute pancreatitis. This study aimed to establish a rat model of severe acute pancreatitis (SAP) for investigating monocyte chemotactic protein-1 (MCP-1) expression in the pathogenesis of the disease. We
Yuya Futagi et al.
Biochemical and biophysical research communications, 495(1), 427-432 (2017-10-11)
The human monocarboxylate transporters (hMCTs/SLC16As) mediate the uptake of various monocarboxylates. Several isoforms of hMCTs are expressed in cancerous tissue as well as in normal tissue. In cancerous tissue, hypoxia induces the expression of hMCT4, which transports the energetic metabolite
Shujun Ge et al.
Journal of neuroinflammation, 9, 171-171 (2012-07-14)
Production of the chemokine CCL2 by cells of the neurovascular unit (NVU) drives critical aspects of neuroinflammation. Suppression of CCL2 therefore holds promise in treating neuroinflammatory disease. Accordingly, we sought to determine if the compound bindarit, which inhibits CCL2 synthesis
Jiro Ogura et al.
Pharmaceutical research, 36(6), 84-84 (2019-04-19)
β-Hydroxy-β-methylbutyrate (HMB), a nutritional supplement, elicits anabolic activity in muscle. Here we investigated the mechanism of HMB uptake in muscle cells. Murine muscle cells (C2C12) and human mammary epithelial cells (MCF7) were used for uptake. As HMB is a monocarboxylate
A Guglielmotti et al.
Inflammation research : official journal of the European Histamine Research Society ... [et al.], 51(5), 252-258 (2002-06-12)
This study was designed to evaluate therapeutic effects of bindarit, an indazolic derivative able to inhibit monocyte chemoattractant protein-1 (MCP-1) production, in adjuvant induced arthritis in rats. Arthritis was induced by Freund's complete adjuvant injection. Bindarit was given as a
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