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Merck

SML2910

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
UNSPSC Code:
51111800
NACRES:
NA.77
MDL number:
MFCD00866723

Key Documents

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Product Name

Bindarit, ≥98% (HPLC)

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

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000396688
0000396688
0000223830
0000223830
0000106376

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C Zoja et al.
Kidney international, 53(3), 726-734 (1998-03-21)
As an alternative to classical immunosuppressants in experimental lupus nephritis, we looked at bindarit, 2-methyl-2-[[1-phenylmethyl)-1H-indazol-3-y1]methoxy]propanoic acid, a novel molecule devoid of immunosuppressive effects, which selectively reduces chronic inflammation in rat adjuvant arthritis. Two groups of NZB/W mice (N = 55
A Guglielmotti et al.
Clinical and experimental rheumatology, 16(2), 149-154 (1998-04-16)
The present study was designed to investigate the effects of bindarit on animal survival and renal damage in murine lupus autoimmune disease. Female NZB/W mice were used. Bindarit was administered, as a 0.5% medicated diet, starting either before the onset
J L Steiner et al.
Cytokine, 66(1), 60-68 (2014-02-20)
Breast cancer, the most deadly cancer in women, is characterized by elevated levels of inflammation within and surrounding the tumor, which can lead to accelerated growth, invasion and metastasis. Macrophages are central to the inflammatory milieu and are recruited to
Massimiliano Mirolo et al.
European cytokine network, 19(3), 119-122 (2008-09-09)
Bindarit is an indazolic derivative that is devoid of any immunosuppressive effects and has no effect on arachidonic acid metabolism. However, it has been proved to have anti-inflammatory activity in a number of experimental diseases, including pancreatitis, arthritis, and lupus
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
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