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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

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About This Item

Empirical Formula (Hill Notation):
C27H36N2O4
CAS Number:
135062-02-1
Molecular Weight:
452.59
MDL number:
MFCD00906179
UNSPSC Code:
12352200
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 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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Deaths in trials should always be reported.
Jeppe Schroll
BMJ (Clinical research ed.), 347, f4219-f4219 (2013-07-06)
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
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
Carolina Säll et al.
Drug metabolism and disposition: the biological fate of chemicals, 40(7), 1279-1289 (2012-03-28)
Repaglinide is presently recommended by the U.S. Food and Drug Administration as a clinical CYP2C8 probe, yet current in vitro and clinical data are inconsistent concerning the role of this enzyme in repaglinide elimination. The aim of the current study
Severe thrombocytopenia due to repaglinide in a patient with type 2 diabetes.
Hisayuki Katsuyama et al.
Diabetes care, 36(3), e36-e36 (2013-02-23)
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