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Submit ReviewNateglinide
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
Biological Activity for Nateglinide
Nateglinide is a 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 for Nateglinide
Nateglinide is also offered as part of the Tocriscreen FDA-Approved Drugs. Find out more about compound libraries available from Tocris.
Technical Data for Nateglinide
| 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.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Nateglinide
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 31.74 | 100 |
Preparing Stock Solutions for Nateglinide
The following data is based on the product molecular weight 317.42. Batch specific molecular weights may vary from batch to batch due to the degree 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 for Nateglinide
References for Nateglinide
References are publications that support the biological activity of the product.
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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