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PZ0189

Sigma-Aldrich

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:
Molecular Weight:
415.87
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

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

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 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.

Legal Information

Sold for research purposes under agreement from Pfizer Inc.

pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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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)
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)

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