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Merck
CN

PZ0189

CP-316819

≥98% (HPLC)

Synonym(s):

5-Chloro-N-[(1S,2R)-2-hydroxy-3-(methoxymethylamino)-3-oxo-1-(phenylmethyl)propyl]-1H-indole-2-carboxamide; GPi 819

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About This Item

Empirical Formula (Hill Notation):
C21H22ClN3O4
CAS Number:
186392-43-8
Molecular Weight:
415.87
UNSPSC Code:
12352200
PubChem Substance ID:
329823763
NACRES:
NA.77

Key Documents

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SMILES string

CON(C)C(=O)[C@H](O)[C@H](Cc1ccccc1)NC(=O)c2cc3cc(Cl)ccc3[nH]2

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

InChI key

WEQLRDLTRCEUHG-PKOBYXMFSA-N

assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

Quality Level

100

Application

CP-316819 has been used as a positive control to study the inhibitory activity against glycogen phosphorylase in vitro.

Biochem/physiol Actions

CP-316819 belongs to the family of indole-2-carboxamide series of phosphorylase inhibitors. It has an ability to regulate interaction of glycogen targeting subunit (GL) 16mer peptide with phosphorylase a.
CP-316819 is a glycogen phosphorylase inhibitor
CP-316819 is a potent glycogen phosphorylase inhibitor. (IC50 = 40 nM against human liver GPα.) Under low glucose conditions, CP-316819 facilitates glycogen utilization in the brain, prevents neuronal cell death and maintains brain electrical currents.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000338163
0000338163
0000301924
0000301925
0000301925

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Synthesis and Antidiabetic Activity of Thiazolo [2, 3-f] Purine Derivatives and Their Analogs
Spasov AA, et al.
Pharmaceutical Chemistry Journal, 51(7), 533-539 (2017)
The hepatic PP1 glycogen-targeting subunit interaction with phosphorylase a can be blocked by C-terminal tyrosine deletion or an indole drug
Kelsall LR, et al.
Febs Letters, 581(24), 4749-4753 (2007)

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