An internal standard for the quantification of nateglinide
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Unlabeled Version(s)
23320Nateglinide
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Nateglinide-d5

Item No. 30151

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[[trans-4-(1-methylethyl)cyclohexyl]carbonyl]-D-phenylalanine-2,3,4,5,6-d5
CAS Number
1227666-13-8
Molecular Formula
C19H22D5NO3
Formula Weight
322.5
Purity
≥99% deuterated forms (d1-d5)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: slightly solubleMethanol: slightly soluble
SMILES
CC(C)[C@H]1CC[C@H](C(N[C@H](CC2=C([2H])C([2H])=C([2H])C([2H])=C2[2H])C(O)=O)=O)CC1
InChi Code
InChI=1S/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15-,16-,17-/m1/s1/i3D,4D,5D,6D,7D
InChi Key
OELFLUMRDSZNSF-LYGNPMIWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $262

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Nateglinide-d5 is intended for use as an internal standard for the quantification of nateglinide (Item No. 23320) by GC- or LC-MS. Nateglinide is a hypoglycemic agent.1,2,3 It induces insulin and somatostatin release from perfused rat pancreas when used at concentrations ranging from 0.03 to 3 μM.1 Nateglinide (3 µM) increases intracellular calcium levels in isolated rat pancreatic β cells, an effect that can be inhibited by the L-type calcium channel blocker nitrendipine (Item No. 17549). Nateglinide-induced secretion of insulin and somatostatin and calcium influx is also reversed by the potassium channel activator diazoxide (Item No. 14576). Oral administration of nateglinide (1.6 mg/kg) reduces blood glucose levels by 20% in fasted mice.2 It also decreases blood glucose levels in an oral glucose tolerance test in normal rats, genetically diabetic KK mice, and a rat model of diabetes induced by streptozotocin (STZ; Item No. 13104).3 Formulations containing nateglinide 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. Fujitani, S., Ikenoue, T., Akiyoshi, M., et al. Somatostatin and insulin secretion due to common mechanisms by a new hypoglycemic agent, A-4166, in perfused rat pancreas. Metabolism 45(2), 184-189 (1996).

    2. Shinkai, H., Toi, K., Kumashiro, I., et al. N-acylphenylalanines and related compounds. A new class of oral hypoglycemic agents. J. Med. Chem. 31(11), 2092-2097 (1988).

    3. Sato, Y., Nishikawa, M., Shinkai, H., et al. Possibility of ideal blood glucose control by a new oral hypoglycemic agent, N-[(trans-4-isopropylcyclohexyl)-carbonyl]-D-phenylalanine (A-4166), and its stimulatory effect on insulin secretion in animals. Diabetes Res. Clin. Pract. 12(1), 53-59 (1991).