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:
Molecular Weight:
341.79
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Quality Level
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 20 mg/mL, clear
storage temp.
room temp
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
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 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.
PF-06409577 is a potent and selective activator of 5′ adenosine monophosphate-activated protein kinase (AMPK).
signalword
Warning
hcodes
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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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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| PZ0319-25MG | 04061833220948 |
| PZ0319-5MG | 04061833220955 |