Repaglinide

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Cat Number

API135062021

CAS Number

135062-02-1

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CAS Number

135062-02-1

EINECS

629-921-1

Storage

Store at room temperature

Synonyms

Prandin; GlucoNorm; Repaglinida; AG-EE 623 ZW; AG-EE 388 ZW; Repaglinidum; enyglid; DTXSID3023552

Molecular Formula

C27H36N2O4

Molecular Weight

452.6

Smiles

CCOC1=C(C=CC(=C1)CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N3CCCCC3)C(=O)O

Appearance

White to off-white powder

Melting Point

129-130.2°C

Boiling Point

672.9±55.0°C (Predicted)

Relative Density

1.137±0.06 (Predicted)

General Description

Repaglinide is a meglitinide derivative with a carbamoylbenzoic acid core and a piperidine ring, structurally distinct from sulfonylureas. Its chemical structure is (S)-2-ethoxy-4-[2-(3-methyl-1-[2-(piperidin-1-yl)phenyl]butylamino)-2-oxoethyl]benzoic acid.

Mechanism of Action

Repaglinide stimulates insulin secretion from the pancreatic beta cells by binding to the ATP-sensitive potassium channels (K-ATP) on the cell membrane, specifically the SUR1 subunit. This binding causes channel closure, membrane depolarization, and calcium influx, triggering the exocytosis of insulin-containing granules. The drug has a rapid onset and short duration of action, mimicking the physiological first-phase insulin release.

Application

Repaglinide is indicated as an adjunct to diet and exercise for the treatment of type 2 diabetes mellitus. It is effective in lowering postprandial glucose levels and is particularly useful in patients with irregular meal schedules. The drug is metabolized by CYP2C8 and CYP3A4 and is generally used in combination with metformin or other agents.

In 60 Chinese patients with newly diagnosed diabetes (HbA1c <10%), repaglinide and metformin similarly improved glycemic parameters and variability over 15 weeks. Repaglinide improved first-phase insulin secretion more markedly. In MIN-6 cells, repaglinide reduced insulin, pericentrin, and F-actin expression at 15 min, with sustained insulin secretion. The PCNT-F-actin pathway mediates repaglinide’s on-demand insulin secretion.

Fig. 1 Intravenous glucose tolerance tests (IVGTTs) 0 to 10 minutes curves and area under curves (AUCs) for the repaglinide group and the metformin group. (Wang LC, et al., 2018)

References

Wang LC, et al. Characteristics of repaglinide and its mechanism of action on insulin secretion in patients with newly diagnosed type-2 diabetes mellitus. Medicine (Baltimore). 2018;97(38):e12476.

In chronic unpredicted mild stress (CUMS)‑induced depression in GK rats, repaglinide pharmacokinetics were significantly altered, with increased plasma cortisol and epinephrine. Liver gene expression profiling identified 49 differentially expressed genes enriched in drug metabolism and steroid hormone pathways. CAR and Ugt1a1 protein expression increased. Dexamethasone and 8‑Br‑cAMP upregulated Ugt1a1, Nr1i2, and PXR in BRL 3A cells. Depression upregulates DMEs via glucocorticoid signaling.

Fig. 2 The network of up-regulated differentially expressed genes in liver tissue of GK rats. (Wei H, et al., 2017)

References

Wei H, et al. Impact of chronic unpredicted mild stress-induced depression on repaglinide fate via glucocorticoid signaling pathway. Oncotarget. 2017;8(27):44351-44365.

Does Repaglinide require protection from light during long-term storage?

Yes, it is photosensitive. UV exposure can cause photodegradation and discoloration. Store in light-resistant containers, preferably amber glass.

What is the recommended storage temperature for Repaglinide?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can soften the powder and accelerate oxidative degradation.

Is Repaglinide stable in tablet formulations with standard excipients?

Yes, when formulated with moisture-protective packaging.

How is the impurity repaglinide N-oxide (an oxidative degradation product) monitored?

This degradation product is quantified using a stability-indicating HPLC method, ensuring it remains within ICH qualification thresholds.