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Repaglinide

Repaglinide Structure
CAS No.
135062-02-1
Chemical Name:
Repaglinide
Synonyms
PRANDIN;Repaglinide API;EP5.2;CS-1998;NOVONORM;AG-EE-623;ag-ee388zw;Repaglinid;Rapaglinide;Rebaglinide
CBNumber:
CB4140539
Molecular Formula:
C27H36N2O4
Molecular Weight:
452.59
MOL File:
135062-02-1.mol
MSDS File:
SDS
Modify Date:
2024/4/12 23:00:59

Repaglinide Properties

Melting point 129-130.2 °C
alpha D20 +6.97° (c = 0.975 in methanol); D20 +7.45° (c = 1.06 in methanol)
Boiling point 672.9±55.0 °C(Predicted)
Density 1.137±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: 34 mg/mL
form solid
pka 4.19±0.10(Predicted)
color white
Water Solubility 89.99mg/L(25 ºC)
Merck 14,8136
InChIKey FAEKWTJYAYMJKF-QHCPKHFHSA-N
SMILES C(O)(=O)C1=CC=C(CC(N[C@H](C2=CC=CC=C2N2CCCCC2)CC(C)C)=O)C=C1OCC
CAS DataBase Reference 135062-02-1(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07,GHS08
Signal word  Warning
Hazard statements  H302-H361-H362
Precautionary statements  P501-P263-P260-P270-P202-P201-P264-P280-P308+P313-P301+P312+P330-P405
WGK Germany  2
RTECS  000000033825
HS Code  2933399090
Toxicity LD50 orally in rats: >1 g/kg (Grell)

Repaglinide price More Price(5)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) R9028 Repaglinide ≥98% (HPLC), solid 135062-02-1 50MG ₹19365.93 2022-06-14 Buy
Sigma-Aldrich(India) R9028 Repaglinide ≥98% (HPLC), solid 135062-02-1 250MG ₹83417.45 2022-06-14 Buy
Sigma-Aldrich(India) PHR3408 Repaglinide pharmaceutical secondary standard, certified reference material 135062-02-1 400MG ₹20643.28 2022-06-14 Buy
TCI Chemicals (India) R0179 Repaglinide 135062-02-1 200MG ₹8900 2022-05-26 Buy
TCI Chemicals (India) R0179 Repaglinide 135062-02-1 1G ₹16300 2022-05-26 Buy
Product number Packaging Price Buy
R9028 50MG ₹19365.93 Buy
R9028 250MG ₹83417.45 Buy
PHR3408 400MG ₹20643.28 Buy
R0179 200MG ₹8900 Buy
R0179 1G ₹16300 Buy

Repaglinide Chemical Properties,Uses,Production

Description

Repaglinide was marketed in the US as an orally active hypoglycemic agent in patients with a type Ⅱ diabetes mellitus, to lower blood glucose in synergistic combination with metformin, when hyperglycemia cannot be controlled by diet, exercise or metformin alone. Chiral (S)-repaglinide can be synthesized in several ways, each involving a stereoselective reduction of an imine or enamine group. Repaglinide is a nonsulfonylurea belonging to the meglitinide family, with an insulin-releasing effect mediated by pancreatic betacells, by closing the ATP-sensitive K+ channels that, in turn, increases the cytosolic concentration of Ca++. In several animal models, repaglinide was more efficient than glibenclamide as a dose-dependant promoter of insulin release, but its mechanism of action is probably slightly different. Repaglinide has a rapid onset of action, a short duration of action and a reduced risk of hypoglycemia compared to glyburide.

Chemical Properties

White to Off-White Solid

Uses

The R-enantiomer showed only weak hypoglycemic activity. Repaglinide impurity

General Description

Repaglinide is 2-ethoxy-4-[2-[[(1S)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid(Prandin); approvals for generics are pending. Combinationsare available with metformin in the United States(Prandimet), and the drug may also be coprescribed with oneof the thiazolidinediones (typically pioglitazone or rosiglitazone;see previous discussion). To establish the most clinicallyvaluable dose, the patient is titrated while monitoringblood glucose levels and hemoglobin glycosylation (HbA1c)as an index of longer-term overall control.

Biological Activity

K ATP channel blocker that binds with high affinity for SUR1 when co-expressed with Kir6.2 (K d = 0.42 nM). Antidiabetic glucose regulator with hypoglycaemic effect in vivo .

Clinical Use

Repaglinide is a nonsulfonylurea insulin secretagogue that was introduced in the United States in 1998 for type 2 diabetes.

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Repaglinide Spectrum

AG-EE-623 ZW (S)-2-Ethoxy-4-[2-[[3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid Repaglinide,(S)-(+)-2-Ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic acid, Novonorm, Prandin Repaglinide (200 mg)G0D2760.999mg/mg(ai) Repaglinide (200 mg) (S)-2-Ethoxy-4-[2-[[[(1S)-3-Methyl-1-[2-(1-piperidinyl)phenyl]butyl]aMino]-2-oxoethyl]benzoic Acid Repaglinide(AG-EE 623ZW) Rebaglinide 2-ethoxy-4-({[(1S)-3-Methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbaMoyl}Methyl)benzoic acid Rapaglinide Repaglinde Solution, 100ppm AG-EE-623 2-ETHOXY-4-[2-[(1S)-3-METHYL-1-[2-(1-PIPERIDINYL)BUTYL]AMINO]-2-OXOETHYL]-BENZOIC ACID REPAGLINIDE (S)-2-ETHOXY-4-(2-(3-METHYL-1-(2-(PIPERIDIN-1-YL)PHENYL)BUTYLAMINO)-2-OXOETHYL)BENZOIC ACID (S)-(+)-2-ETHOXY-4-[N-[1-(2-PIPERIDINOPHENYL)-3-METHYL-1-BUTYL]AMINOCARBONYLMETHYL]BENZOIC ACID NOVONORM (S)-(+)-2-Ethoxy-4-[[[N-[1-(2-piperidinophenyl)-3-methylbutyl]amino]carbonyl]methyl]benzoic acid Benzoic acid, 2-ethoxy-4-(2-((3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)- 2-oxoethyl)-, (S)- 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-oxo-ethyl]benzoic acid 2-ethoxy-4-[2-keto-2-[[(1S)-3-methyl-1-(2-piperidinophenyl)butyl]amino]ethyl]benzoic acid ag-ee388zw Prandin, 2-Ethoxy-4-[2-[[(1S)-3-methyl-1-[2-(1-piperidinyl)butyl]amino]-2-oxoethyl]-benzoic Acid, AG-EE-623, Novonorm, S(+)-2-Ethoxy-4-(2-oxo-2-((alpha-isobutyl-2-piperidinobenzyl)amino)ethyl)benzoesure 2-Ethoxy-4-[2-[[(1R)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic Acid AG-EE 624ZW 4-Carboxy-3-ethoxybenzeneacetic Acid 2-Ethoxy-4-[2-[[[(1S)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic Acid Novonorm, Prandin, (S)-(+)-2-Ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic acid 2-ethoxy-4-[2-[[3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acid EP5.2 CS-1998 (S)-2-Ethoxy-4-[2-[[3-methyl-1-[2-(1-piperidyl)phenyl]butyl]amino]-2-oxoethyl]benzoic Acid Repaglinide CRS Repaglinide> Repaglinide for system suitability CRS Benzoic acid, 2-ethoxy-4-[2-[[(1S)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]- Repaglinide USP/EP/BP RepaglinideQ: What is Repaglinide Q: What is the CAS Number of Repaglinide Q: What is the storage condition of Repaglinide Q: What are the applications of Repaglinide Repaglinide (1600813) Repaglinide,(S)-(+)-2-Ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic acid, Novon Repaglinide API PRANDIN Benzenemethanol,α-(aminomethyl)-8-bromo- methyl 3-[4-cyano-4-[phenyl(propanoyl)amino]piperidin-1-yl]propanoate Repaglinid Repaglinde Reference Standard 135062-02-1 35062-02-1 135062-02-6 C27H36N2O4 Pharmaceutical raw material DTIC-DOME API Aromatics Heterocycles Amino Acids 13C, 2H, 15N