CP-316819

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H22ClN3O4
Molecular Weight	415.87
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CON(C)C(=O)[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)C2=CC3=C(N2)C=CC(Cl)=C3

InChI

InChIKey=WEQLRDLTRCEUHG-PKOBYXMFSA-N

InChI=1S/C21H22ClN3O4/c1-25(29-2)21(28)19(26)17(10-13-6-4-3-5-7-13)24-20(27)18-12-14-11-15(22)8-9-16(14)23-18/h3-9,11-12,17,19,23,26H,10H2,1-2H3,(H,24,27)/t17-,19+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17251391
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/16046314

CP 316819 is the selective glycogen phosphorylase inhibitor. CP 316819 has been extensively evaluated as antihyperglycemic agents for type 2 diabetes because of its potential to limit hepatic production of glucose from glycogen without inducing hypoglycemia. Under low glucose conditions, CP 316819 facilitates glycogen utilization in the brain, prevents neuronal cell death and maintains brain electrical currents.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscle glycogen phosphorylase 1 Target ID: CHEMBL3526 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16046314	Inhibitor 8297		100.0 nM [IC50]
Liver glycogen phosphorylase 3 Target ID: CHEMBL2568 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17870073	Inhibitor 8297		57.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17251391 https://www.ncbi.nlm.nih.gov/pubmed/16046314 https://www.ncbi.nlm.nih.gov/pubmed/17870073	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Glycogen phosphorylase inhibition in type 2 diabetes therapy: a systematic evaluation of metabolic and functional effects in rat skeletal muscle.	2005 Aug	16046314
Astrocyte glycogen sustains neuronal activity during hypoglycemia: studies with the glycogen phosphorylase inhibitor CP-316,819 ([R-R,S]-5-chloro-N-[2-hydroxy-3-(methoxymethylamino)-3-oxo-1-(phenylmethyl)propyl]-1H-indole-2-carboxamide).	2007 Apr	17251391

Patents

Sample Use Guides

In Vivo Use Guide

Initial dose - 150 mg/kg (5 ml/kg), with subsequent injections of 50 mg/kg (5 ml/kg) 12 and 16 h later

Route of Administration: Intraperitoneal

In Vitro Use Guide

CP-316819 treatment reduced AMP-mediated activation of glycogen phosphorylase in muscle obtained after 10 min of submaximal intensity contraction compared with control (112.5 [control] vs. 88.0 [CP-316819] mmol*kg-1 dry muscle*min-1, P < 0.001).

Name

Type

Language

CP-316819

Code

English

GPI-819

Code

English

1H-INDOLE-2-CARBOXAMIDE, 5-CHLORO-N-(2-HYDROXY-3-(METHOXYMETHYLAMINO)-3-OXO-1-(PHENYLMETHYL)PROPYL)-, (R-(R*,S*))-

Systematic Name

English

1H-INDOLE-2-CARBOXAMIDE, 5-CHLORO-N-((1S,2R)-2-HYDROXY-3-(METHOXYMETHYLAMINO)-3-OXO-1-(PHENYLMETHYL)PROPYL)-

Systematic Name

English

CP316819

Code

English

GPI819

Code

English

5-CHLORO-N-((2S,3R)-3-HYDROXY-4-(METHOXY(METHYL)AMINO)-4-OXO-1-PHENYLBUTAN-2-YL)-1H-INDOLE-2-CARBOXAMIDE

Systematic Name

English

Code System Code Type Description

FDA UNII

WN4ZZX5ECD