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PZ0189

Sigma-Aldrich

CP-316819

≥98% (HPLC)

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Synonym(s):
5-Chloro-N-[(1S,2R)-2-hydroxy-3-(methoxymethylamino)-3-oxo-1-(phenylmethyl)propyl]-1H-indole-2-carboxamide; GPi 819
Empirical Formula (Hill Notation):
C21H22ClN3O4
CAS Number:
186392-43-8
Molecular Weight:
415.87
UNSPSC Code:
12352200
PubChem Substance ID:
329823763
NACRES:
NA.77

Quality Level

100

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
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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