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Key Documents

5.08336

Sigma-Aldrich

TAK-242

≥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

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

Related Categories

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)

Storage Class Code

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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