An inhibitor of MCP production
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Isomer(s)
18723Oxyphenbutazone
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Bindarit

Item No. 11479

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-methyl-2-[[1-(phenylmethyl)-1H-indazol-3-yl]methoxy]-propanoic acid
CAS Number
130641-38-2
Synonyms
  • AF 2838
Molecular Formula
C19H20N2O3
Formula Weight
324.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/mlEthanol: 20 mg/ml
λmax
209, 294 nm
SMILES
OC(C(C)(C)OCC1=NN(CC2=CC=CC=C2)C3=CC=CC=C31)=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    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.1 It inhibits LPS- or C. albicans-induced production of MCP-1/CCL2 in isolated human monocytes (IC50s = 172 and 403 µM, respectively).2 Bindarit downregulates NF-κB signaling and prevents p65 and p65/p50-mediated MCP-1/CCL2 promoter activation in RAW264.7 cells.3 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.4 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.5 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 MCT1.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mirolo, M., Fabbri, M., Sironi, M., et al. Impact of the anti-inflammatory agent bindarit on the chemokinome: Selective inhibition of the monocyte chemotactic proteins. Eur. Cytokine Netw. 19(3), 119-122 (2008).

    2. Sironi, M., Guglielmotti, A., Polentarutti, N., et al. A small synthetic molecule capable of preferentially inhibiting the production of the CC chemokine monocyte chemotactic protein-1. Eur. Cytokine Netw. 10(3), 437-442 (1999).

    3. Mora, E., Guglielmotti, A., Biondi, G., et al. Bindarit: An anti-inflammatory small molecule that modulates the NFκB pathway. Cell Cycle 11(1), 159-169 (2016).

    4. Zoja, C., Corna, D., Benedetti, G., et al. Bindarit retards renal disease and prolongs survival in murine lupus autoimmune disease. Kidney Int. 53(3), 726-734 (1998).

    5. Ge, S., Shrestha, B., Paul, D., et al. The CCL2 synthesis inhibitor bindarit targets cells of the neurovascular unit, and suppresses experimental autoimmune encephalomyelitis. J. Neuroinflammation 9, 171 (2012).

    6. Futagi, Y., Kobayashi, M., Narumi, K., et al. Identification of a selective inhibitor of human monocarboxylate transporter 4. Biochem. Biophys. Res. Commun. 495(1), 427-432 (2018).

    Product Citations

    Futagi, Y., Kobayashi, M., Narumi, K., et al. Identification of a selective inhibitor of human monocarboxylate transporter 4. Biochem. Biophys. Res. Commun. 495(1), 427-432 (2018).