An internal standard for the quantification of gliclazide
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Unlabeled Version(s)
25503Gliclazide
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Gliclazide-d4

Item No. 33610

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[[(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)amino]carbonyl]-4-methyl-benzene-2,3,5,6-d4-sulfonamide
CAS Number
1185039-30-8
Molecular Formula
C15H17D4N3O3S
Formula Weight
327.4
Purity
≥99% deuterated forms (d1-d4)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: soluble
SMILES
CC1=C([2H])C([2H])=C(S(NC(NN2CC3C(CCC3)C2)=O)(=O)=O)C([2H])=C1[2H]
InChi Code
InChI=1S/C15H21N3O3S/c1-11-5-7-14(8-6-11)22(20,21)17-15(19)16-18-9-12-3-2-4-13(12)10-18/h5-8,12-13H,2-4,9-10H2,1H3,(H2,16,17,19)/i5D,6D,7D,8D
InChi Key
BOVGTQGAOIONJV-KDWZCNHSSA-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

    Gliclazide-d4 is intended for use as an internal standard for the quantification of gliclazide (Item No. 25503) by GC- or LC-MS. Gliclazide is a sulfonylurea and an inhibitor of pancreatic β-cell ATP-sensitive potassium (KATP) channels (IC50 = 184 nM for murine β-cells).1,2 It is selective for pancreatic β-cell over cardiac and arterial smooth muscle cell KATP channels (IC50s = 19.5 and 37.9 μM, respectively).1 Gliclazide (5 μM) increases insulin-induced glucose uptake and glucose transporter 4 (GLUT4) translocation to the plasma membrane in a differentiated 3T3L1 adipocyte model of insulin resistance induced by hydrogen peroxide.3 Gliclazide (5 and 10 μg/ml) reduces LDL oxidation by human aortic smooth muscle cells (HASMCs), decreasing TBARS content and 8-isoprostane levels.4 It also decreases oxidized LDL-induced HASMC proliferation and monocyte adhesion when used at concentrations ranging from 1 to 10 μg/ml. Gliclazide (5 mg/kg) reduces serum glucose levels and increases glucose uptake by isolated rat hindquarters in a model of diabetes induced by streptozotocin (STZ; Item No. 13104).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lawrence, C.L., Proks, P., Rodrigo, G.C., et al. Gliclazide produces high-affinity block of KATP channels in mouse isolated pancreatic beta cells but not rat heart or arterial smooth muscle cells. Diabetologia 44(8), 1019-1025 (2001).

    2. Proks, P., Reimann, F., Green, N., et al. Sulfonylurea stimulation of insulin secretion. Diabetes 51(3), S368-S376 (2002).

    3. Shimoyama, T., Yamaguchi, S., Takahashi, K., et al. Gliclazide protects 3T3L1 adipocytes against insulin resistance induced by hydrogen peroxide with restoration of GLUT4 translocation. Metabolism 55(6), 722-730 (2006).

    4. Mamputu, J.C., and Renier, G. Gliclazide decreases vascular smooth muscle cell dysfuntion induced by cell-meditated oxidized low-density lipoprotein. Metabolism 50(6), 688-695 (2001).

    5. Pulido, N., Suarez, A., Casanova, B., et al. Gliclazide treatment of streptozotocin diabetic rats restores GLUT4 protein content and basal glucose uptake in skeletal muscle. Metabolism 46(12 Suppl 1), 10-13 (1997).