346021 | Glucokinase Activator, Cpd A - CAS 603108-44-7 - Calbiochem

346021
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical FormulaCAS #
      C₁₄H₁₄N₆OS₂ 603108-44-7

      Pricing & Availability

      Catalog NumberAvailability Packaging Qty/Pack Price Quantity
      346021-5MG
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          Plastic ampoule 5 mg
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          Description
          OverviewA cell-permeable thiazolylamide glucokinase (GK; Hexokinase IV/D) activator that reversibly targets a allosteric site that is only exposed for binding in the glucose-bound GK conformation, but not in the unbound "super-open" GK conformation or the GKRP- (GK Regulatory Protein) bound GK, and effectively stabilizes GK in an active conformation as well as prevents its interaction with and nuclear sequestration by GKRP, while exhibiting little effect against Hexokinase I/II/III. Compound A is shown to activate GK activity in cell-free assays (EC50 = 0.42 and 0.14 µM in the presence of 2.5 mM and 10 mM of glucose, respectively) and effectively induce cellular GK activation and increase glucose metabolism both in in rats (10 to 30 mg/kg, p.o.) in vivo and in rat islets and hepatocytes cultures (10 to 30 µM) in vitro.
          Catalogue Number346021
          Brand Family Calbiochem®
          SynonymsHexokinase D Activator, Hexokinase IV Activator, 2-Amino-5-(4-methyl-4H-(1,2,4)-triazole-3-yl-sulfanyl)-N-(4-methyl-thiazole-2-yl)benzamide, Compound A
          References
          ReferencesIino, T., et al. 2009. Bioorg. Med. Chem. Lett. 19, 5531.
          Mitsuya, M., et al. 2009. Bioorg. Med. Chem. Lett. 19, 2718.
          Nishimura, T., et al. 2009. Bioorg. Med. Chem. Lett. 19, In press.
          Futamura, M., et al. 2006. J. Biol. Chem. 281, 1357.
          Kamata, K., et al. 2004. Structure 12, 429.
          Product Information
          CAS number603108-44-7
          FormOff-white solid
          Hill FormulaC₁₄H₁₄N₆OS₂
          Chemical formulaC₁₄H₁₄N₆OS₂
          Structure formula ImageStructure formula Image
          Applications
          Biological Information
          Purity≥95% by HPLC
          Physicochemical Information
          Dimensions
          Materials Information
          Toxicological Information
          Safety Information according to GHS
          Safety Information
          S PhraseS: 22-24/25-36

          Do not breathe dust.
          Avoid contact with skin and eyes.
          Wear suitable protective clothing.
          Product Usage Statements
          Storage and Shipping Information
          Ship Code Ambient Temperature Only
          Toxicity Standard Handling
          Storage +2°C to +8°C
          Protect from Light Protect from light
          Do not freeze Ok to freeze
          Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
          Packaging Information
          Packaged under inert gas Packaged under inert gas
          Transport Information
          Supplemental Information
          Specifications

          Documentation

          SDS

          Title

          Safety Data Sheet (SDS) 

          Certificates of Analysis

          TitleLot Number
          346021

          References

          Reference overview
          Iino, T., et al. 2009. Bioorg. Med. Chem. Lett. 19, 5531.
          Mitsuya, M., et al. 2009. Bioorg. Med. Chem. Lett. 19, 2718.
          Nishimura, T., et al. 2009. Bioorg. Med. Chem. Lett. 19, In press.
          Futamura, M., et al. 2006. J. Biol. Chem. 281, 1357.
          Kamata, K., et al. 2004. Structure 12, 429.
          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.

          Revision08-April-2011 RFH
          SynonymsHexokinase D Activator, Hexokinase IV Activator, 2-Amino-5-(4-methyl-4H-(1,2,4)-triazole-3-yl-sulfanyl)-N-(4-methyl-thiazole-2-yl)benzamide, Compound A
          DescriptionA cell-permeable thiazolylamide glucokinase (GK; Hexokinase IV/D) activator that reversibly targets a allosteric site that is only exposed for binding in the glucose-bound GK conformation, but not in the unbound "super-open" GK conformation or the GKRP- (GK Regulatory Protein) bound GK, and effectively stabilizes GK in an active conformation as well as prevents its interaction with and nuclear sequestration by GKRP, while exhibiting little effect against Hexokinase I/II/III. Compound A is shown to activate GK activity in cell-free assays (EC50 = 0.42 and 0.14 µM in the presence of 2.5 mM and 10 mM of glucose, respectively) and effectively induce cellular GK activation and increase glucose metabolism both in in rats (10 to 30 mg/kg, p.o.) in vivo and in rat islets and hepatocytes cultures (10 to 30 µM) in vitro.
          FormOff-white solid
          Intert gas (Yes/No) Packaged under inert gas
          CAS number603108-44-7
          Chemical formulaC₁₄H₁₄N₆OS₂
          Structure formulaStructure formula
          Purity≥95% by HPLC
          SolubilityDMSO (5 mg/ml)
          Storage +2°C to +8°C
          Protect from light
          Do Not Freeze Ok to freeze
          Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
          Toxicity Standard Handling
          ReferencesIino, T., et al. 2009. Bioorg. Med. Chem. Lett. 19, 5531.
          Mitsuya, M., et al. 2009. Bioorg. Med. Chem. Lett. 19, 2718.
          Nishimura, T., et al. 2009. Bioorg. Med. Chem. Lett. 19, In press.
          Futamura, M., et al. 2006. J. Biol. Chem. 281, 1357.
          Kamata, K., et al. 2004. Structure 12, 429.