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R9028

Sigma-Aldrich

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:
Molecular Weight:
452.59
MDL number:
PubChem Substance ID:

Quality Level

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

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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.

Packaging

50, 250 mg in glass bottle

Biochem/physiol Actions

Repaglinide (RPG) due to its fast-acting effect prevents hypoglycemia. The KATP 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 (KATP) 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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R9028.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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