TAK 242

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Cat.No. 6587 - TAK 242 | C15H17ClFNO4S | CAS No. 243984-11-4
Description: TLR4 signaling inhibitor
Chemical Name: (R)-Ethyl 6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-enecarboxylate
Purity: ≥98% (HPLC)
Datasheet
Citations
Reviews
Literature
Pathways

Biological Activity

Toll-like receptor 4 (TLR4) signaling inhibitor. Binds to intracellular domain of TLR4. Inhibits LPS-induced cytokine production in vitro (IC50 values are 1.3, 1.3 and 3.2 nM for IL-6, TNFα and NO production). Reduces lesion volume in a mouse model of cerebral cavernous malformations (CCMs). Also attenuates increased cytokine levels in a mouse sepsis model, when given in combination with ceftazidime. Cell permeable.

Technical Data

M. Wt 361.82
Formula C15H17ClFNO4S
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 243984-11-4
PubChem ID 11703255
InChI Key LEEIJTHMHDMWLJ-CQSZACIVSA-N
Smiles CCOC(C1=CCCC[C@H]1S(=O)(NC2=C(C=C(C=C2)F)Cl)=O)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
ethanol 36.18 100
DMSO 36.18 100

Preparing Stock Solutions

The following data is based on the product molecular weight 361.82. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.76 mL 13.82 mL 27.64 mL
5 mM 0.55 mL 2.76 mL 5.53 mL
10 mM 0.28 mL 1.38 mL 2.76 mL
50 mM 0.06 mL 0.28 mL 0.55 mL

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References

References are publications that support the biological activity of the product.

Yamada et al (2005) Discovery of novel and potent small-molecule inhibitors of NO and cytokine production as antisepsis agents: synthesis and biological activity of alkyl 6-(N-substituted sulfamoyl)cyclohex-1-ene-1-carboxylate. J.Med.Chem. 48 7457 PMID: 16279805

Ii et al (2006) A novel cyclohexene derivative, ethyl (6R)-6-[N-(2-Chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate (TAK-242), selectively inhibits toll-like receptor 4-mediated cytokine production through suppression of intracellular signal Mol.Pharmacol. 69 1288 PMID: 16373689

Tang et al (2017) Endothelial TLR4 and the microbiome drive cerebral cavernous malformations. Nature 545 305 PMID: 28489816

Takashima et al (2009) Analysis of binding site for the novel small-molecule TLR4 signal transduction inhibitor TAK-242 and its therapeutic effect on mouse sepsis model. Br.J.Pharmacol. 157 1250 PMID: 19563534


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Citations for TAK 242

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Literature in this Area

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Pathways for TAK 242

Toll-like Receptor

Toll-like Receptor Signaling Pathway

TLR signaling is involved in the cellular response to threatening molecules such as bacteria and viruses. It results in an inflammatory and immmunological response.