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614316 TLR4 Inhibitor, TAK-242 - CAS 243984-11-4 - Calbiochem

TAK-242; CAS 243984-11-4; is a cell-permeable compound that selectively binds to Cys747 of TLR4 and selectively disrupts its interaction with adaptor molecules TIRAP and TRAM.

MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: Ethyl-(6R)-6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate

Primary Target: TLR4
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Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
243984-11-4C₁₅H₁₇ClFNO₄S

Products

Catalogue NumberPackaging Qty/Pack
614316-5MGCN Glass bottle 5 mg
Description
OverviewA cell-permeable cyclohexenecarboxylate that disrupts TLR4, but not TLR1-3 or TLR5-10, interaction with adaptor molecules TIRAP and TRAM via direct binding to TLR4 intracellular Cys747 residue.Shown to effectively inhibit TLR4-mediated cellular events (IC50 = 1.8, 1.3, and 1.9 nM, respectively, against LPS-induced NO, IL-6, and TNF-α production in murine RAW264.7 macrophages) in vitro and completely prevent LPS- (7 mg/kg, i.p.) induced death in mice (3 mg/kg; i.v.) in vivo. Also available as a 25 mM solution in DMSO (Cat. No. 508336).
Catalogue Number614316
Brand Family Calbiochem®
SynonymsEthyl-(6R)-6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate
References
ReferencesMatsunaga, 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.
Product Information
CAS number243984-11-4
FormWhite to yellowish white solid
Hill FormulaC₁₅H₁₇ClFNO₄S
Chemical formulaC₁₅H₁₇ClFNO₄S
ReversibleY
Structure formula ImageStructure formula Image
Quality LevelMQ100
Applications
Biological Information
Primary TargetTLR4
Purity≥98% by HPLC
Physicochemical Information
Cell permeableY
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
Safety Information
R PhraseR: 22

Harmful if swallowed.
S PhraseS: 26-36

In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
Wear suitable protective clothing.
Product Usage Statements
Storage and Shipping Information
Ship Code Shipped at Ambient Temperature or with Blue Ice or with Dry Ice
Toxicity Harmful
Storage +2°C to +8°C
Protect from Light Protect from light
Do not freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-70°C). Stock solutions are stable for up to 1 year at -70°C. Use only fresh DMSO.
Packaging Information
Packaged under inert gas Packaged under inert gas
Transport Information
Supplemental Information
Specifications
Global Trade Item Number
Catalogue Number GTIN
614316-5MGCN 04055977186635

Documentation

TLR4 Inhibitor, TAK-242 - CAS 243984-11-4 - Calbiochem Certificates of Analysis

TitleLot Number
614316

References

Reference overview
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.
Data Sheet

Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

Revision27-February-2018 JSW
SynonymsEthyl-(6R)-6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-1-ene-1-carboxylate
DescriptionA 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.).
FormWhite to yellowish white solid
Intert gas (Yes/No) Packaged under inert gas
CAS number243984-11-4
Chemical formulaC₁₅H₁₇ClFNO₄S
Structure formulaStructure formula
Purity≥98% by HPLC
SolubilityDMSO (100 mg/ml)
Storage Protect from light
+2°C to +8°C
Do Not Freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-70°C). Stock solutions are stable for up to 1 year at -70°C. Use only fresh DMSO.
Toxicity Harmful
ReferencesMatsunaga, 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.