Nateglinide

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Cat.No. 4231 - Nateglinide | C19H27NO3 | CAS No. 105816-04-4
Description: Kir6 (KATP) blocker; displays high affinity for SUR1/Kir6.2 channels
Alternative Names: A-4166, Senaglinide
Chemical Name: N-[[4-(1-Methylethyl)cyclohexyl]carbonyl]-D-phenylalanine
Datasheet
Citations
Reviews
Literature

Biological Activity

Kir6 (KATP) blocker. Exhibits in vitro tissue selectivity for pancreatic β-cell-type Kir6 channels over cardiovascular Kir6 channels; displays high affinity for SUR1/Kir6.2 channels. Hypoglycemic agent; stimulates insulin secretion from pancreatic β-cells by increasing cytosolic Ca2+ concentration. Also agonist at the orphan receptor MRGPRX4.

Compound Libraries

Nateglinide is also offered as part of the Tocriscreen Plus and Tocriscreen Library of FDA-Approved Compounds. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 317.42
Formula C19H27NO3
Storage Store at RT
CAS Number 105816-04-4
PubChem ID 5311309
InChI Key OELFLUMRDSZNSF-OFLPRAFFSA-N
Smiles O=[C@](N[C@@H](C(O)=O)CC2=CC=CC=C2)[C@H]1CC[C@H]([C@H](C)C)CC1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 31.74 100

Preparing Stock Solutions

The following data is based on the product molecular weight 317.42. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3.15 mL 15.75 mL 31.5 mL
5 mM 0.63 mL 3.15 mL 6.3 mL
10 mM 0.32 mL 1.58 mL 3.15 mL
50 mM 0.06 mL 0.32 mL 0.63 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the products' biological activity.

Shinkai et al (1989) N-(cyclohexylcarbonyl)-D-phenylalanines and related compounds. A new class of hypoglycemic agents. J.Med.Chem. 32 1436 PMID: 2738878

Fujitani et al (1997) The ability of a new hypoglycemic agent, A-4166, compared to sulphonylureas, to increase cytosolic Ca2+ in pancreatic beta-cells under metabolic inhibition. Br.J.Pharmacol. 120 1191 PMID: 9105692

Hu et al (1999) Tissue selectivity of antidiabetic agent nateglinide: study on cardiovascular and β-cell KATP channels. J.Pharmacol.Exp.Ther. 291 1372 PMID: 10565863

Chachin et al (2003) Nateglinide, a D-phenylalanine derivative lacking either a sulfonylurea or benzamido moiety, specifically inhibits pancreatic β-cell-type KATP channels. J.Pharmacol.Exp.Ther. 304 1025 PMID: 12604678

Kroeze et al (2015) PRESTO-Tango as an open-source resource for interrogation of the druggable human GPCRome. Nat.Struct.Mol.Biol. 22 362 PMID: 25895059


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