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Merck
CN

PZ0319

PF-06409577

≥98% (HPLC)

Synonym(s):

6-Chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C19H16ClNO3
CAS Number:
1467057-23-3
Molecular Weight:
341.79
UNSPSC Code:
12352200
PubChem Substance ID:
329823837
NACRES:
NA.77

Key Documents

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SMILES string

ClC1=C(C2=CC=C(C3(O)CCC3)C=C2)C=C4C(NC=C4C(O)=O)=C1

InChI

1S/C19H16ClNO3/c20-16-9-17-14(15(10-21-17)18(22)23)8-13(16)11-2-4-12(5-3-11)19(24)6-1-7-19/h2-5,8-10,21,24H,1,6-7H2,(H,22,23)

InChI key

FHQXLWCFSUSXBF-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

room temp

Quality Level

100

General description

PF-06409577 is a 6-chloro-indole derivative obtained from 5-bromo-6-chloro-indole.

Application

PF-06409577 has been used to determine its potential as a therapeutic agent for diabetic nephropathy.

Biochem/physiol Actions

PF-06409577 is a potent and selective activator of 5′ adenosine monophosphate-activated protein kinase (AMPK).
PF-06409577 potently activates a1β1γ1 AMPK (5′ adenosine monophosphate-activated protein kinase) isoform, and prevents its dephosphorylation. It is similarly potent for β1 containing isoforms, but shows significantly lower potency for β2-containing isoforms of AMPK. Patch-clamp assays show that this compound does not inhibit hERG (human ether-a-go-go gene). It interacts with the allosteric drug and metabolite site (ADaM) of AMPK.
PF-06409577 preserves retinal pigment epithelium cells from UV radiation by activating AMPK (AMP-activated protein kinase) signaling. This orally bioavailable and possesses pharmacokinetic properties. PF-06409577 blocks de novo lipid and cholesterol synthesis pathways that shows a decrease in hepatic lipids and mRNA expression of markers of hepatic fibrosis.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000231700
0000231701
0000231701
0000231700
0000105166

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Activation of Liver AMPK with PF-06409577 Corrects NAFLD and Lowers Cholesterol in Rodent and Primate Preclinical Models.
Esquejo RM, et al.
EBioMedicine, 31, 122-132 (2018)
PF-06409577 activates AMPK signaling to protect retinal pigment epithelium cells from UV radiation.
Li X F, et al.
Biochemical and Biophysical Research Communications, 501(1), 293-299 (2018)
Discovery and Preclinical Characterization of 6-Chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylic Acid (PF-06409577), a Direct Activator of Adenosine Monophosphate-activated Protein Kinase (AMPK), for the Potential Treatment of Diabetic Nephropathy.
Cameron KO et al
Journal of Medicinal Chemistry, 59(17), 8068-8081 (2016)
Nereida Jiménez de Oya et al.
Antimicrobial agents and chemotherapy, 62(7) (2018-05-02)
Mosquito-borne flaviviruses are a group of RNA viruses that constitute global threats for human and animal health. Replication of these pathogens is strictly dependent on cellular lipid metabolism. We have evaluated the effect of the pharmacological activation of AMP-activated protein

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