Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H22ClN3O3 |
| Molecular Weight | 399.871 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)C(=O)[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)C2=CC3=C(N2)C=CC(Cl)=C3
InChI
InChIKey=HINJNZFCMLSBCI-PKOBYXMFSA-N
InChI=1S/C21H22ClN3O3/c1-25(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
| Molecular Formula | C21H22ClN3O3 |
| Molecular Weight | 399.871 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/2943673
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/2943673
CP-91149 is a selective glycogen phosphorylase (GP) inhibitor in the presence of glucose, 5- to 10-fold less potent in the absence of glucose. It may be useful in the treatment of type 2 diabetes. In vivo, oral injection of CP-91149 to diabetic ob/ob mice at 25–50 mg/kg led in rapid (3 h) glucose lowering by 100–120 mg/dl without producing hypoglycemia. In addition, upon treatment with CP-91149, A549 non-small cell lung carcinoma (NSCLC) cells accumulated glycogen with associated growth retardation. Treated normal skin fibroblasts also accumulated glycogen with G1-cell cycle arrest that was associated with inhibition of cyclin E-CDK2 activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Discovery of a human liver glycogen phosphorylase inhibitor that lowers blood glucose in vivo. | 1998 Feb 17 |
|
| Hepatic glycogen synthesis is highly sensitive to phosphorylase activity: evidence from metabolic control analysis. | 2001 Jun 29 |
|
| Inhibition of glycogen phosphorylase (GP) by CP-91,149 induces growth inhibition correlating with brain GP expression. | 2003 Sep 12 |
|
| Regulation of glycogen metabolism in cultured human muscles by the glycogen phosphorylase inhibitor CP-91149. | 2004 Mar 15 |
Patents
Sample Use Guides
diabetic ob/ob mice: oral administration of CP-91149 to at 25-50 mg/kg resulted in rapid (3 h) glucose lowering by 100-120 mg/dl (P < 0.001) without producing hypoglycemia. Further, CP-91149 treatment did not lower glucose levels in normoglycemic, nondiabetic mice.
Route of Administration:
Oral
It was analyzed the effect of 10 uM CP-91149 on non-engineered or glycogen phosphorylase (GP)-overexpressing cultured human muscle cells. CP-91149 treatment decreased muscle GP activity by (1) converting the phosphorylated AMP-independent a form into the dephosphorylated AMP-dependent b form and (2) inhibiting GP a activity and AMP-mediated GP b activation. Treatment with CP-91149 impairs muscle glycogen breakdown, but enhances its recovery.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:18:39 GMT 2023
by
admin
on
Sat Dec 16 08:18:39 GMT 2023
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| Record UNII |
O8EV00W45A
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID70171897
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