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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

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      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
      614316-5MG 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.