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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 of REPAGLINIDE, (-)-

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

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

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

Sample Use Guides

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 GMT 2023
Edited
by admin
on Sat Dec 16 09:26:03 GMT 2023
Record UNII
85M30X62FM
Record Status Validated (UNII)
Record Version
  • Download
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
USP-RS  
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
Created by admin on Sat Dec 16 09:26:03 GMT 2023 , Edited by admin on Sat Dec 16 09:26:03 GMT 2023
PRIMARY
FDA UNII
85M30X62FM
Created by admin on Sat Dec 16 09:26:03 GMT 2023 , Edited by admin on Sat Dec 16 09:26:03 GMT 2023
PRIMARY
RS_ITEM_NUM
1600868
Created by admin on Sat Dec 16 09:26:03 GMT 2023 , Edited by admin on Sat Dec 16 09:26:03 GMT 2023
PRIMARY
CAS
147852-26-4
Created by admin on Sat Dec 16 09:26:03 GMT 2023 , Edited by admin on Sat Dec 16 09:26:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID70163818
Created by admin on Sat Dec 16 09:26:03 GMT 2023 , Edited by admin on Sat Dec 16 09:26:03 GMT 2023
PRIMARY
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP