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5.08336

TAK-242

Name: TAK-242
Brand: MM

≥98% (HPLC), α-D-galactosidase Substrate, liquid

Synonym(s):

InSolution TLR4 Inhibitor, TAK-242, Ethyl-(6R)-6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate, (R)-Ethyl 6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-enecarboxylate, TLR4 Inhibitor, TAK-242 InSolution, TLR4 Inhibitor, TAK-242 InSolution, Ethyl-(6R)-6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate, (R)-Ethyl 6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-enecarboxylate

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₁₇ClFNO₄S

CAS Number:

243984-11-4

Molecular Weight:

361.82

MDL number:

MFCD11046362

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

liquid

Quality level:

100

Storage condition:

OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light

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Properties

Product Name

TAK-242, InSolution, ≥98%, 25 mM in DMSO, TLR4 inhibitor

Quality Level

100

assay

≥98% (HPLC)

form

liquid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light

storage temp.

−70°C

SMILES string

Fc1cc(c(cc1)N[S](=O)(=O)[C@@H]2CCCC=C2C(=O)OCC)Cl

InChI

1S/C15H17ClFNO4S/c1-2-22-15(19)11-5-3-4-6-14(11)23(20,21)18-13-8-7-10(17)9-12(13)16/h5,7-9,14,18H,2-4,6H2,1H3/t14-/m1/s1

InChI key

LEEIJTHMHDMWLJ-CQSZACIVSA-N

Description

General description

A cell-permeable cyclohexenecarboxylate that disrupts TLR4 interaction with adaptor molecules TIRAP and TRAM by selectively binding to TLR4, but not TLR1-3 or TLR5-10, via TLR4 intracellular Cys747 residue. Shown to effectively inhibit TLR4-mediated signaling events, including LPS-induced NO and inflammatory cytokines production in murine RAW264.7 macrophages (IC₅₀ = 1.8, 1.3, and 1.9 nM, respectively, against NO, IL-6, and TNF-α production), TLR4/TIRAP-dependent NF-κB activity as well as TLR4/TIRAP- and TLR4/TRAM-dependent ISRE activity (IC₅₀<300 nM) in HEK293-hTLR4/MD2-CD14 transfected with either TIRAP or TRAM. When administered at an i.v. dose of 3 mg/kg, TAK-242 is reported to completely prevent LPS- (7 mg/kg, i.p.) induced death in mice in vivo. Complete elimination of septic shock-induced death can be extended to live E. coli-infected mice when co-administered with ceftazidime (3 mg/kg TAK-242 and 20 mg/kg ceftazidime, i.v.).

Biochem/physiol Actions

Cell permeable: yes

Primary Target
TLR4

Reversible: no

Packaging

Packaged under inert gas

Physical form

A 25 mM (2 mg/221 µL) sterile-filtered solution of TLR4 Inhibitor, TAK-242 (Cat. No. 614316) in DMSO.

Preparation Note

Following initial thaw, aliquot and freeze (-70°C). Aliquots are stable for up to 1 year at -70°C.

Other Notes

Matsunaga, N., et al. 2011. Mol. Pharmacol.79, 34.
Takashima, K., et al. 2009. Br. J. Pharmacol.157, 1250.
Li, M., et al. 2006. Mol. Pharmacol.69, 1288.
Yamada, M., et al. 2005. J. Med. Chem.48, 7457.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

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Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

188.6 °F - (refers to pure substance)

flash_point_c

87 °C - (refers to pure substance)

Certificates of Analysis (COA)

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Global Trade Item Number

SKU	GTIN
5083360001	04055977261905