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530613 | IRAP Inhibitor, HFI-419 - Calbiochem

530613
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical Formula
      C₁₉H₁₈N₂O₅

      Pricing & Availability

      Catalog NumberAvailability Packaging Qty/Pack Price Quantity
      5.30613.0001
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          Glass bottle 10 mg
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          Description
          OverviewThe racemic mixture of an aqueous soluble pyridinyl-4H-benzopyran compound that inhibits insulin-regulated aminopeptidase (IRAP) activity by competing against substrate for IRAP extracellular catalytic site binding (Ki = 0.48 µM against 25 µM Leu-AMC), while displaying little potency against glucose-6-phosphatase, aminopeptidae N, ACE1, leukotriene A4 hydrolase, or ER-associated aminopeptidases 1 & 2. Reported to boost 1 mM dibutyryl cAMP-evoked glucose uptake in cultured rat hippocampal slices (68% higher uptake with 100 nM HFI-419 than dbcAMP alone) in vitro and exhibit in vivo memory-enhancing efficacay in an object recognition test via direct cerebral lateral ventricle administration (0.1 or 1.0 nmol/2 µL/rat). HFI-419 is reported to hydrolyze into the less potent HFI-142 (Ki = 2.0 µM) after i.v. or i.p. injection in rats, although HFI-142 is more stable and likely exhibits better blood-brain permeability.
          Catalogue Number530613
          Brand Family Calbiochem®
          Synonyms(±)-Ethyl-2-acetamido-7-hydroxy-4-(pyridin-3-yl)-4H-chromene-3-carboxylate, HFI419, Insulin-Regulated Aminopeptidase Inhibitor
          References
          ReferencesMountford, S.J., et al. 2014. J. Med. Chem. 57, 1368.
          Albiston, A.L., et al. 2011. Br. J. Pharmacol. 164, 37.
          Albiston, A.L., et al. 2010. Mol. Pharmacol. 78, 600.
          Albiston, A.L., et al. 2008. FASEB J. 22, 4209.
          Product Information
          FormOff-white powder
          Hill FormulaC₁₉H₁₈N₂O₅
          Chemical formulaC₁₉H₁₈N₂O₅
          ReversibleY
          Applications
          Biological Information
          Primary TargetIRAP
          Purity≥97% by HPLC
          Physicochemical Information
          Cell permeableY
          Dimensions
          Materials Information
          Toxicological Information
          Safety Information according to GHS
          Safety Information
          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 3 months at -20°C.
          Packaging Information
          Packaged under inert gas Packaged under inert gas
          Transport Information
          Supplemental Information
          Specifications

          Documentation

          References

          Reference overview
          Mountford, S.J., et al. 2014. J. Med. Chem. 57, 1368.
          Albiston, A.L., et al. 2011. Br. J. Pharmacol. 164, 37.
          Albiston, A.L., et al. 2010. Mol. Pharmacol. 78, 600.
          Albiston, A.L., et al. 2008. FASEB J. 22, 4209.
          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.

          Revision06-June-2014 JSW
          Synonyms(±)-Ethyl-2-acetamido-7-hydroxy-4-(pyridin-3-yl)-4H-chromene-3-carboxylate, HFI419, Insulin-Regulated Aminopeptidase Inhibitor
          DescriptionThe racemic mixture of an aqueous soluble (at least 50 µg/mL or 140 µM at pH 6.5) pyridinyl-4H-benzopyran compound that inhibits insulin-regulated (IRAP) aminopeptidase activity by competing against substrate for IRAP extracellular catalytic site binding (Ki = 0.48 µM; using 25 µM Leu-AMC as substrate) with concomitant interaction with active site zinc via its acetamide, while displaying little potency against glucose-6-phosphatase, aminopeptidase N, ACE1, leukotriene A4 hydrolase, or ER-associated aminopeptidases 1 & 2 (≤13% inhibition at 100 µM). Reported to boost 1 mM dibutyryl cAMP-evoked glucose uptake in cultured rat hippocampal slices (68% higher uptake in 5 min than dbcAMP alone without 100 nM HFI-419) in vitro and exhibit in vivo memory-enhancing efficacay in an object recognition test when administered directly into the cerebral lateral ventricle of rats via a cannula implant (0.1 or 1.0 nmol/2 µL/rat). HFI-419 is reported to hydrolyze into slightly less potent HFI-142 (Ki = 2.0 µM) after i.v. (plasma t1/2 = 11 min; 2 mg/kg) or i.p (plasma t1/2 = 4.6 h; 10 mg/kg) injection in rats, although HFI-142 is more stable and likely exhibits better blood-brain permeability (Blood:Brain HFI-142 ratio = 3.36 and 0.38, respectively, 0.5 and 4 h post single 3 mg HFI-419/kg i.v. injection).
          FormOff-white powder
          Intert gas (Yes/No) Packaged under inert gas
          Chemical formulaC₁₉H₁₈N₂O₅
          Purity≥97% by HPLC
          SolubilityDMSO (100 mg/ml). Use only fresh DMSO for reconstitution.
          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 3 months at -20°C.
          Toxicity Standard Handling
          ReferencesMountford, S.J., et al. 2014. J. Med. Chem. 57, 1368.
          Albiston, A.L., et al. 2011. Br. J. Pharmacol. 164, 37.
          Albiston, A.L., et al. 2010. Mol. Pharmacol. 78, 600.
          Albiston, A.L., et al. 2008. FASEB J. 22, 4209.