Repaglinide

Names

[ Name ]:
Repaglinide

[Synonym ]:
(S)-2-Ethoxy-4-(2-((3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)amino)-2-oxoethyl)benzoic acid
(S)-(+)-2-Ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic acid
(S)-2-ethoxy-4-(2-(3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)benzoic acid
Repaglinid
2-Ethoxy-4-[2-[[(1S)-3-Methyl-1-[2-(1-Piperidinyl)Phenyl]Butyl]Amino]-2-Oxoethyl]Benzoic Acid
AG EE-623 ZW
(+)-2-Ethoxy-a-[[(S)-a-isobutyl-o-piperidinobenzyl]carbamoyl]-p-toluic acid
MFCD00906179
2-ethoxy-4-[2-({(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl}amino)-2-oxoethyl]benzoic acid
Prandin,GlucoNorm,NovoNorm
2-Ethoxy-4-[2-({(1S)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl}amino)-2-oxoethyl]benzoic acid
Benzoic acid, 2-ethoxy-4-[2-[[(1S)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]-
(S)-2-Ethoxy-4-[2-[[3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid
Repaglinide
2-ethoxy-4-[2-[[(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acid
2-ethoxy-4-(2-{[(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino}-2-oxoethyl)benzoic acid

Biological Activity

[Description]:

Repaglinide(AG-EE 623ZW) is a carbamoylmethyl benzoic acid (CMBA) derivative, which recently has become available for the treatment of type II diabetes. IC50 value:Target: Repaglinide is very rapidly absorbed (tmax less than 1 hour) with a t1/2 of less than one hour. Furthermore, repaglinide is inactivated in the liver and more than 90 % excreted via the bile. Repaglinide (1 mg/kg p.o.) was effective (P < 0.001) as an insulin-releasing agent in a rat model (low-dose streptozotocin) of type 2 diabetes.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[References]

[1]. Marbury T, Huang WC, Strange P, Lebovitz H et al. Repaglinide versus glyburide: a one-year comparison trial. Diabetes Research and Clinical Practice .1999, 43(3):155-166.

[2]. David R. Owens . Repaglinide-prandial glucose regulator: a new class of oral antidiabetic drugs . Diabetic Medicine 1998,15 : S28-S36.

[3]. J Fuhlendorff, P Rorsman, H Kofod. Stimulation of insulin release by repaglinide and glibenclamide involves both common and distinct processes. Diabetes. 1998. 47 (3): 345-351 .

[4]. R Moses, R Slobodniuk, S Boyages. Effect of repaglinide addition to metformin monotherapy on glycemic control in patients with type 2 diabetes. Diabetes Care . 22 (1 ) : 119-124 .

[5]. Julio Rosenstock, MD, David R. Hassman, DO, Robert D. Madder, DO. Diabetes Care June 2004 vol. 27 no. 6 1265-1270

[6]. Shiling Hu1, Shuya Wang1, Barbara Fanelli1. Pancreatic β-Cell KATP Channel Activity and Membrane-Binding Studies with Nateglinide: A Comparison with Sulfonylureas and Repaglinide . JPET , 2000,293 (2 ): 444-452 .

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
672.9±55.0 °C at 760 mmHg

[ Melting Point ]:
129-130.2 °C

[ Molecular Formula ]:
C₂₇H₃₆N₂O₄

[ Molecular Weight ]:
452.586

[ Flash Point ]:
360.8±31.5 °C

[ Exact Mass ]:
452.267517

[ PSA ]:
78.87000

[ LogP ]:
4.69

[ Vapour Pressure ]:
0.0±2.2 mmHg at 25°C

[ Index of Refraction ]:
1.568

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: 34 mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
000000033825

[ HS Code ]:
2933399090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933399090

[ Summary ]:
2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

[symbol: see text] Nateglinide and [symbol: see text] repaglinide for type 2 diabetes?

Drug Ther. Bull. 41(7) , 52-4, (2003)

[symbol: see text] Nateglinide (Starlix-Novartis) and [symbol: see text] repaglinide (NovoNorm-Novo Nordisk) are two of a new class of orally active antidiabetic drugs, the meglitinides. They have a r...

Drug-drug and food-drug pharmacokinetic interactions with new insulinotropic agents repaglinide and nateglinide.

Clin. Pharmacokinet. 46(2) , 93-108, (2007)

This review describes the current knowledge on drug-drug and food-drug interactions with repaglinide and nateglinide. These two meglitinide derivatives, commonly called glinides, have been developed f...

Analysis of the repaglinide concentration increase produced by gemfibrozil and itraconazole based on the inhibition of the hepatic uptake transporter and metabolic enzymes.

Drug Metab. Dispos. 41(2) , 362-71, (2013)

The plasma concentration of repaglinide is reported to increase greatly when given after repeated oral administration of itraconazole and gemfibrozil. The present study analyzed this interaction based...