108157-52-4

Basic information

• Product Name: Repaglinide
• Synonyms: BenzeneMethanaMine, a-(2-Methylpropyl)-2-(1-piperidinyl)-
• CAS NO: 108157-52-4
• Molecular Formula: C16H26N2
• Molecular Weight: 246.39104
• Mol File: 108157-52-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 179-180℃
• Boiling Point: 672.9°C at 760 mmHg
• Flash Point: 360.8°C
• Appearance: /
• Density: 0.990
• Vapor Pressure: 5E-19mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: Repaglinide(CAS DataBase Reference)
• NIST Chemistry Reference: Repaglinide(108157-52-4)
• EPA Substance Registry System: Repaglinide(108157-52-4)

Safety Data

• Hazardous Substances Data: 108157-52-4(Hazardous Substances Data)

Usage

General Description

Repaglinide is a type of oral anti-diabetic drug that is often used for the treatment of type 2 diabetes. It belongs to the meglitinides class of medicines, which induce insulin secretion from the pancreas, thereby controlling blood sugar levels. The effectiveness of Repaglinide can be negatively impacted by certain types of medications, and its usage may result in side effects including weight gain, low blood sugar, upper respiratory infection, and headaches. It is not recommended for people with diabetic ketoacidosis or type 1 diabetes.

InChI:InChI=1/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

Upstream product

• 394-47-8 2-fluorobenzonitrile 
• 626219-78-1 3-methyl-1-(2-fluorophenyl)butan-1-one 
• 765306-66-9 3-methyl-1-(2-fluorophenyl)butan-1-ol 
• 446-52-6 2-Fluorobenzaldehyde 
• 147770-03-4 3-methyl-1-(2-piperidin-1-yl-phenyl)-butan-1-one 
• 219921-93-4 (R)-3-methyl-1-(2-(1-pieridinyl)phenyl)-butylamine 
• 765306-65-8 3-methyl-1-[2-(1-piperidinyl)phenyl]butoxime 
• 873-32-5 2-Chlorobenzonitrile 
• 72752-52-4 2-(piperidin-1-yl)benzonitrile 
• 110-89-4 piperidine 
• 147769-96-8 3-methyl-1-[2-(piperidin-1-yl)phenyl]butan-1-imine 

Downstream Products

• 108175-51-5 ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate 
• 219921-93-4 (R)-3-methyl-1-(2-(1-pieridinyl)phenyl)-butylamine 
• 147769-93-5 (1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butan-1-amine 
• 1334218-78-8 S-PPA*3,5-DNTA 
• 1334218-75-5 rac-PPA*3,5-DNTA 
• 881002-43-3 4-[1-(3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)aminocarbonylmethyl]phenol 
• 147770-08-9 (R)-(-)-ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate 
• 108157-53-5 (S)-(+)-2-ethoxy-4-[N-[1-(2-piperidino-phenyl)-3-methyl-1-butyl]amino-carbonylmethyl]benzoic acid 
• 147769-98-0 N-acetyl-N-<(S)-3-methyl-1-(2-(1-piperidinyl)phenyl)-1-butyl>-amine 
• 147770-06-7 (S)-(+)-ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate 
• 135062-02-1 (S)-repaglinide 
• 1098066-89-7 (S)-3-methyl-1-(2-piperidino-phenyl)-1-butylamine di-p-toluoyl-D-tartaric acid salt 

Related news

A floating-type dosage form of Repaglinide (cas 108157-52-4) in polycarbonate microspheres08/31/2019

ObjectiveTo prepare a floating type dosage form for the anti-diabetic drug repaglinide using polycarbonate (PC) microspheres capable of floating in the gastro-intestinal fluid to improve the biological half life and bioavailability of the drug.detailed

Development of Repaglinide (cas 108157-52-4) microspheres using novel acetylated starches of bitter and Chinese yams as polymers08/30/2019

Tropical starches from Dioscorea dumetorum (bitter) and Dioscorea oppositifolia (Chinese) yams were acetylated with acetic anhydride in pyridine medium and utilized as polymers for the delivery of repaglinide in microsphere formulations in comparison to ethyl cellulose. Acetylated starches of bi...detailed

Conformational flexibility and packing plausibility of Repaglinide (cas 108157-52-4) polymorphs08/25/2019

The present manuscript highlights the structural insight into the repaglinide polymorphs. The experimental screening for the possible crystal forms were carried out using various solvents, which generated three forms. The crystal structure of Form II and III was determined using PXRD pattern whe...detailed

Identification of Repaglinide (cas 108157-52-4) as a therapeutic drug for glioblastoma multiforme08/24/2019

Glioblastoma multiforme (GBM) is a highly aggressive brain tumor with a median survival time of only 14 months after treatment. It is urgent to find new therapeutic drugs that increase survival time of GBM patients. To achieve this goal, we screened differentially expressed genes between long-te...detailed

Endocrine pharmacologyCharacteristics of Repaglinide (cas 108157-52-4) effects on insulin secretion08/23/2019

The dynamics of insulin secretion stimulated by repaglinide, a glinide, and the combinatorial effects of repaglinide and incretin were investigated. At 4.4 mM glucose, repaglinide induced insulin secretion with a gradually increasing first phase, showing different dynamics from that induced by g...detailed

ArticleThe Structural Basis for the Binding of Repaglinide (cas 108157-52-4) to the Pancreatic KATP Channel08/22/2019

SummaryRepaglinide (RPG) is a short-acting insulin secretagogue widely prescribed for the treatment of type 2 diabetes. It boosts insulin secretion by inhibiting the pancreatic ATP-sensitive potassium channel (KATP). However, the mechanisms by which RPG binds to the KATP channel are poorly under...detailed

Relevant articles and documents

An improved process for repaglinide via an efficient and one pot process of (1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butan-1-amine - A useful intermediate

The development of a large-scale synthesis for (1S)-3-methyl-1-(2- piperidin-1-ylphenyl)butan-1-amine (S-(+)-1), a key intermediate of repaglinide (2), is described. The process conditions for S-(+)-1 involving nucleophilic substitution, Grignard reaction, reduction and resolution were optimized and telescoped. The racemization of the undesired enantiomer R-(-)-1 offers a distinctive advantage in terms of cost and overall yield over the existing process. This communication also describes the control of a DCU byproduct obtained during the condensation of S-(+)-1 with phenyl acetic acid derivative 3 in the synthesis of 2. Schweizerische Chemische Gesellschaft.

Preparation of 3-methyl-1 - [2 - (1-piperidinyl) phenyl] ding Yaan and the method of use of the product of

The invention discloses a method for preparing 3-methyl-1-(2-(1-piperidyl) phenyl) butyl imine and the application of the 3-methyl-1-(2-(1-piperidyl) phenyl) butyl imine. The yield of the 3-methyl-1-(2-(1-piperidyl) phenyl) butyl imine is 30 to 35 percent; the purity of the 3-methyl-1-(2-(1-piperidyl) phenyl) butyl imine is 99.0 to 99.5 percent (detected by an HPLC (high performance liquid chromatography) method); the 3-methyl-1-(2-(1-piperidyl) phenyl) butyl imine can be used as a standard substance for detecting impurities during the preparation of repaglinide amine, and can also be used for preparing high-purity repaglinide amine after subjected to catalytic hydrogenation or preparing 3-methyl-1-(2-(1-piperidyl) butanone after subjected to acidolysis; and the prepared 3-methyl-1-(2-(1-piperidyl) butanone can be used as raw material for synthesizing repaglinide amine or 3-methyl-1-(2-(1-piperidyl) phenyl) butyl imine, so as to be recycled, and raw material waste is avoided. The method is applicable to the synthesis of repaglinide amine.

Process for the preparation of substantially optically pure Repaglinide and precursors thereof

The invention relates to a process for preparing substantially optically pure Repaglinide and pharmaceutically acceptable salts, solvates and esters thereof, as well as precursors therefore.