| Identification | Back Directory | [Name]
CP 91149 | [CAS]
186392-40-5 | [Synonyms]
CS-231
CP 91149
CP 91149 USP/EP/BP
5-chloro-N-((2S,3R)-4-(dimethylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-1H-indole-2-carboxamide
5-Chloro-N-[(1S,2R)-3-(diMethylaMino)-2-hydroxy-3-oxo-1-(phenylMethyl)propyl]-1H-indole-2-carboxaMide
[R-(R*,S*)]-5-Chloro-N-[3-(diMethylaMino)-2-hydroxy-3-oxo-
1-(phenylMethyl)propyl]-1H-indole-2-carboxaMide | [Molecular Formula]
C21H21ClN3O3 | [MDL Number]
MFCD00954145 | [MOL File]
186392-40-5.mol | [Molecular Weight]
398.863 |
| Chemical Properties | Back Directory | [Melting point ]
190-192°C | [storage temp. ]
2-8°C | [solubility ]
DMSO: >20mg/mL | [form ]
powder | [color ]
white to off-white | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [Description]
CP 91,149 is an inhibitor of human liver glycogen phosphorylase a (LGPa), muscle glycogen phosphorylase a (MGPa), and MGPb (IC50s = 0.13, 0.2, and 0.3 μM, respectively, in the presence of glucose). CP 91,149 is 5- to 10-fold less potent in the absence of glucose. In vitro, it inhibits glucagon-stimulated glycogenolysis in primary human hepatocytes (IC50 = 2.1 μM) and increases glycogen synthesis in rat hepatocytes at a concentration of 2.5 μM in the presence of 5 mM glucose. CP 91,149 inhibits brain GP (IC50 = 0.5 μM) and, at a concentration of 30 μM, inhibits glycogen accumulation and proliferation of A549 non-small cell lung carcinoma (NSCLC) cells that express endogenous brain GP. In vivo, CP 91,149 (25 mg/kg, p.o.) lowers the plasma glucose level in diabetic ob/ob mice within 3 hours of administration without producing hypoglycemia, but has no effect on normoglycemic, non-diabetic mice. | [Chemical Properties]
White Solid | [Uses]
Inhibition of glycogen phosphorylase (GP) by CP-91,149 induces growth inhibition correlating with brain GP expression. Antitumor agent.
| [Biochem/physiol Actions]
CP-91149 is a selective glycogen phosphorylase inhibitor. | [in vitro]
cp-91149 treatment suppressed glycogenolysis stimulated by glucagon in in primary human hepatocytes and isolated rat hepatocytes with ic50 value of 2.1 μm and 10–100 μm, respectively 1. inhibition of phosphorylase a by cp-91149 resulted in activation of glycogen synthase and translocation of the protein from a soluble to a particulate fraction, which mimicked the insulin- stimulated glycogen synthesis 2. | [in vivo]
treatment of cp-91149 on diabetic ob/ob mice at a dosage of 25–50 mg/kg was shown to lead to a rapid glucose lowering but did not change glucose levels in normoglycemic, nondiabetic mice 1. | [target]
GP | [storage]
Store at -20°C | [References]
1. martin wh, hoover dj, armento sj, et al. discovery of a human liver glycogen phosphorylase inhibitor that lowers blood glucose in vivo. proceedings of the national academy of sciences of the united states of america. 1998;95(4):1776-1781.2. aiston s, coghlan mp, agius l. inactivation of phosphorylase is a major component of the mechanism by which insulin stimulates hepatic glycogen synthesis. european journal of biochemistry / febs. 2003;270(13):2773-2781. |
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