REPAGLINIDE, (-)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H36N2O4
Molecular Weight	452.5857
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC1=C(C=CC(CC(=O)N[C@H](CC(C)C)C2=C(C=CC=C2)N3CCCCC3)=C1)C(O)=O

InChI

InChIKey=FAEKWTJYAYMJKF-HSZRJFAPSA-N

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-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C27H36N2O4
Molecular Weight	452.5857
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9283692 | https://www.ncbi.nlm.nih.gov/pubmed/22618022

R-enantiomer, AG-EE 624 ZW, is more than 100 fold less active than S-enantiomer as hypoglycaemic compound. It is critical to test and control the content of R(–) isomer in repaglinide to assure the quality of tablet. Repaglinide is an oral medication used for blood sugar control in type 2 diabetes mellitus.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Highly potent and stereoselective effects of the benzoic acid derivative AZ-DF 265 on pancreatic beta-cells.	1988 Jan	3280060
Control of insulin secretion by sulfonylureas, meglitinide and diazoxide in relation to their binding to the sulfonylurea receptor in pancreatic islets.	1989 Apr 15	2650685
Hypoglycaemic effects of the novel antidiabetic agent repaglinide in rats and dogs.	1997 Aug	9283692
Repaglinide, a novel, short-acting hypoglycemic agent for type 2 diabetes mellitus.	1998 Nov-Dec	9855316

Patents

Sample Use Guides

In Vivo Use Guide

Rat, Oral: 0.1, 0.3 and 1.0 mg/kg Rat, Intravenous: 0.1, 1 mg/kg

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:26:03 UTC 2023` Edited by `admin` on `Sat Dec 16 09:26:03 UTC 2023`
Record UNII	85M30X62FM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

REPAGLINIDE, (-)-

Common Name

English

BENZOIC ACID, 2-ETHOXY-4-(2-(((1R)-3-METHYL-1-(2-(1-PIPERIDINYL)PHENYL)BUTYL)AMINO)-2-OXOETHYL)-

Systematic Name

English

2-ETHOXY-4-(2-(((1R)-3-METHYL-1-(2-(PIPERIDIN-1-YL)PHENYL)BUTYL)AMINO)-2-OXOETHYL)BENZOIC ACID

Systematic Name

English

AG-EE 624ZW

Code

English

REPAGLINIDE RELATED COMPOUND E

Common Name

English

REPAGLINIDE RELATED COMPOUND E [USP-RS]

Common Name

English

REPAGLINIDE IMPURITY E [EP IMPURITY]

Common Name

English

REPAGLINIDE RELATED COMPOUND E [USP IMPURITY]

Common Name

English

AG-EE-624ZW

Code

English

Code System Code Type Description

PUBCHEM

10479034