R9028

Repaglinide

≥98% (HPLC), solid

• Synonym(s): (S)-(+)-2-Ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic acid, Novonorm, Prandin
• Empirical Formula (Hill Notation): C₂₇H₃₆N₂O₄
• CAS Number: 135062-02-1
• Molecular Weight: 452.59
• MDL number: MFCD00906179
• UNSPSC Code: 12352200
• PubChem Substance ID: 24724596
• NACRES: NA.77

Properties

• assay: ≥98% (HPLC)
• form: solid
• color: white
• mp: 129-130.2 °C
• solubility: DMSO: >20 mg/mL
• originator: Novo Nordisk
• storage temp.: 2-8°C
• SMILES string: CCOc1cc(CC(=O)N[C@@H](CC(C)C)c2ccccc2N3CCCCC3)ccc1C(O)=O
• InChI: 1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1
• InChI key: FAEKWTJYAYMJKF-QHCPKHFHSA-N
• Gene Information: human ... ABCC8(6833) , KCNJ1(3758) , KCNJ11(3767)

Description

General description

Repaglinide belongs to the meglitinide class, which differs from the glibenclamide by having a bulky B site group instead of A site.

Application

Repaglinide has been used as a ATP-sensitive potassium channel (KATP) inhibitor in breast cancer cell line MDA-MB-231. It has also been used in the preparation of KATP complex to study its interaction using cryo-EM structural analysis.

Biochem/physiol Actions

Repaglinide (RPG) due to its fast-acting effect prevents hypoglycemia. The K_ATP inhibition by RPG leads to depolarization in pancreatic β cells leading in voltage-gated calcium channel activation triggering insulin release. Repaglinide favors calcein passage and improves the gap junctional intercellular communication (GJIC). Structurally, RPG binds to the ABC transporter sulfonylurea receptor 1 (SUR1) in the transmembrane bundle.

Repaglinide is a potent short-acting insulin secretagogue that acts by closing ATP-sensitive potassium (K_ATP) channels in the plasma membrane of the pancreatic beta cell. It represents a new class of insulin secretagogues, structurally unrelated to sulphonylureas, which were developed for the treatment of type 2 diabetes.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Novo Nordisk. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)