An internal standard for the quantification of glyburide
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Unlabeled Version(s)
15009Glyburide (potassium salt)
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Glyburide-d3

Item No. 25740

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-(methoxy-d3)-benzamide
CAS Number
1219803-02-7
Synonyms
  • Glibenclamide-d3
Molecular Formula
C23H25ClD3N3O5S
Formula Weight
497.0
Purity
≥99% deuterated forms (d1-d3)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
SMILES
ClC1=CC(C(NCCC2=CC=C(S(NC(NC3CCCCC3)=O)(=O)=O)C=C2)=O)=C(OC([2H])([2H])[2H])C=C1
InChi Code
InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)/i1D3
InChi Key
ZNNLBTZKUZBEKO-FIBGUPNXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Glyburide-d3 is intended for use as an internal standard for the quantification of glyburide (Item No. 15009) by GC- or LC-MS. Glyburide is a sulfonylurea and an inhibitor of sulfonylurea receptor 1 (SUR1) linked to ATP-sensitive potassium channel Kir6.2 (IC50 = 4.3 nM).1 It binds to microsomes derived from RINm5F pancreatic β-cells (Kd = 0.3 nM) and inhibits 86Rb+ efflux from intact RINm5 cells with a half-maximal inhibition (K0.5) value of 0.06 nM.2 Glyburide (5 mg/kg) reduces blood glucose levels and increases the activity of hepatic glutathione-S-transferase (GST) and glucose-6-phosphate dehydrogenase (G6PDH) in a rat model of diabetes induced by streptozotocin (STZ; Item No. 13104).3 It inhibits ATP-induced increases in caspase-1 activation and IL-1β and IL-18 secretion in a concentration-dependent manner in LPS-primed bone marrow-derived macrophages (BMDMs).4 Glyburide (80 mg/ml) also reduces lesion growth in mice infected with L. mexicana.5 Formulations containing glyburide have been used in the treatment of type 2 diabetes.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Coghlan, M.J., Carroll, W.A., and Gopalakrishnan, M. Recent developments in the biology and medicinal chemistry of potassium channel modulators: Update from a decade of progress. J. Med. Chem. 44(11), 1627-1653 (2001).

    2. Schmid-Antomarchi, H., De Weille, J., Fosset, M., et al. The receptor for antidiabetic sulfonylureas controls the activity of the ATP-modulated K+ channel in insulin-secreting cells. The Journal of Biological Chemisty 262(33), 15840-15844 (1987).

    3. Bugdayci, G., Altan, N., Sancak, B., et al. The effect of the sulfonylurea glyburide on glutathione-S-transferase and glucose-6-phosphate dehydrogenase in streptozotocin-induced diabetic rat liver. Acta. Diabetol. 43(4), 131-134 (2006).

    4. Lamkanfi, M., Mueller, J.L., Vitari, A.C., et al. Glyburide inhibits the Cryopyrin/Nalp3 inflammasome. J. Cell Biol. 187(1), 61-70 (2009).

    5. Serrano-Martín, X., Payares, G., and Mendoza-León, A. Glibenclamide, a blocker of K+ATP channels, shows antileishmanial activity in experimental murine cutaneous leishmaniasis. Antimicrob. Agents Chemother. 50(12), 4214-4216 (2006).