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R9028

Repaglinide

Name: Repaglinide
Brand: SIGMA

≥98% (HPLC), solid

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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

PubChem Substance ID:

24724596

Quality Level

100

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)

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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.

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.

Storage Class Code

11 - 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

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Mechanism of pharmacochaperoning in a mammalian KATP channel revealed by cryo-EM

Martin GM, et al.

eLife, 8 (2019)

Zoledronic Acid as a Novel Dual Blocker of KIR6.1/2-SUR2 Subunits of ATP-Sensitive K+ Channels: Role in the Adverse Drug Reactions.

Fatima Maqoud et al.

Pharmaceutics, 13(9) (2021-09-29)

Zoledronic acid (ZOL) is used as a bone-specific antiresorptive drug with antimyeloma effects. Adverse drug reactions (A.D.R.) are associated with ZOL-therapy, whose mechanics are unknown. ZOL is a nitrogen-containing molecule whose structure shows similarities with nucleotides, ligands of ATP-sensitive K+

Subsets of ATP-sensitive potassium channel (KATP) inhibitors increase gap junctional intercellular communication in metastatic cancer cell lines independent of SUR expression.

Thomas M Bodenstine et al.

FEBS letters, 586(1), 27-31 (2011-11-29)

Gap junctional intercellular communication (GJIC) regulates cellular homeostasis by propagating signaling molecules, exchanging cellular metabolites, and coupling electrical signals. In cancer, cells exhibit altered rates of GJIC which may play a role in neoplastic progression. K(ATP) channels help maintain membrane

Discrepancies among consensus documents, guidelines, clinical practice and the legal framework for the treatment of type 2 diabetes mellitus patients.

Carlos del Pozo-Fernández et al.

Nefrologia : publicacion oficial de la Sociedad Espanola Nefrologia, 32(3), 367-373 (2012-05-18)

In this paper we analyse the discrepancies that exist in the widespread prescription of metformin in patients with type 2 diabetes and the lack of guidelines concerning its prescription in the different stages of renal failure. This cross-sectional study includes

Validated stability-indicating spectrofluorimetric method with enhanced sensitivity for determination of repaglinide in tablets.

Rania N El-Shaheny

Journal of fluorescence, 22(6), 1587-1594 (2012-07-04)

A simple and highly sensitive spectrofluorimetric method was developed and validated for determination of the antidiabetic agent repaglinide (RG) in tablets. The proposed method is based on measurement of the native fluorescence of RG in 0.1 M H(2)SO(4)/methanol medium at

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