Repaglinide

SIGMA/R9028 - ≥98% (HPLC), solid

Synonym: (S)-(+)-2-Ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic acid; Novonorm; Prandin

CAS Number: 135062-02-1
Empirical Formula (Hill Notation): C₂₇H₃₆N₂O₄
Molecular Weight: 452.59
MDL Number: MFCD00906179
Linear Formula: C₂₇H₃₆N₂O₄
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-R9028-50MG	50 mg	$242.00 1/EA	Add To Favorites
45-R9028-250MG	250 mg	$651.00 1/EA	Add To Favorites

Properties
Descriptions
Safety Info.
Basic Data

assay	≥98% (HPLC)
color	white
form	solid
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
mp	129-130.2 °C
originator	Novo Nordisk
Quality Level	100
SMILES string	CCOc1cc(CC(=O)N[C@@H](CC(C)C)c2ccccc2N3CCCCC3)ccc1C(O)=O
solubility	DMSO: >20 mg/mL
storage temp.	2-8°C

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.
Biochem/physiol Actions:	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.
Biochem/physiol Actions:	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 .
Features and Benefits:	This compound was developed by Novo Nordisk . To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here .
General description:	Repaglinide belongs to the meglitinide class, which differs from the glibenclamide by having a bulky B site group instead of A site.
Packaging:	50, 250 mg in glass bottle

RIDADR	NONH for all modes of transport
WGK Germany	WGK 2
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥98% (HPLC)
mp	129-130.2 °C
Storage Temp.	2-8°C
UNSPSC	12352200

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