Basic information
- CAS
1467057-23-3- Standard SMILES
O=C(O)c1c[nH]c2cc(Cl)c(-c3ccc(C4(O)CCC4)cc3)cc12- InChIKey
FHQXLWCFSUSXBF-UHFFFAOYSA-N- Molecular formula
- C19H16ClNO3
- Average molar mass
- 341.8 g/mol
- Monoisotopic mass
- 341.08187105
Overview
PF-06409577 is a chloroindole that is 6-chloro-1H-indole substituted by carboxy and 4-(1-hydroxycyclobutyl)phenyl groups at positions 3 and 5, respectively. It is a potent and selective allosteric activator of AMPK and a potential treatment for diabetic nephropathy. It has a role as an antiatherosclerotic agent, an antineoplastic agent, a nephroprotective agent and an EC 2.7.11.31 {[hydroxymethylglutaryl-CoA reductase (NADPH)] kinase} activator. It is a member of cyclobutanes, a member of benzenes, a tertiary alcohol, an indolecarboxylic acid and a chloroindole.
Names & identifiers
- Preferred name
- PF-06409577
- IUPAC
- 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylic acid
- English name
- 6-chloro-5-(4-(1-hydroxycyclobutyl)phenyl)-1H-indole-3-carboxylicacid
- Molecular formula
- C19H16ClNO3
- Molecular weight
- 341.79
Names & synonyms
1467057-23-3PF-064095776-Chloro-5-(4-(1-hydroxycyclobutyl)phenyl)-1H-indole-3-carboxylic acid6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylic acidA89WAM8FBHRefChem:202572110-458-4PF 064095771H-Indole-3-carboxylic acid, 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-MFCD29917835EX-A2599s8335
Show more names
CS-2760EOS-61684PF 6409577PF-06409577 ，S8335PF-06409577 >=98% (HPLC)PF-06409577, 10 mM in DMSO6-chloro-5-(4-(1-hydroxycyclobutyl)phenyl)-1H-indole-3-carboxylicacid
AKOS030211017CCG-267937CS-8071PF-6409577PF064095776-Chloranyl-5-[4-(1-Oxidanylcyclobutyl)phenyl]-1~{h}-Indole-3-Carboxylic AcidUS9394285, 1Q27456575
Database identifiers
- CAS
1467057-23-3
Properties
Computed structural properties
- XLogP
- 3.6
- Topological polar surface area
- 73.3 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 487
Physicochemical properties
- Boiling point
- 610.9 · 610.9±55.0 °C(Predicted)
- Density
- 1.468 · 1.468±0.06 g/cm3(Predicted)
- storage temp.
- room temp
- solubility
- DMSO: soluble
- form
- powder
- pka
- 3.6 · 3.60±0.30(Predicted)
- color
- white to beige
- InChI
- 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)
- InChIKey
- FHQXLWCFSUSXBF-UHFFFAOYSA-N
- SMILES
- N1C2=C(C=C(C3=CC=C(C4(O)CCC4)C=C3)C(Cl)=C2)C(C(O)=O)=C1
- FDA UNII
- 89 WAM8FBH · A89WAM8FBH
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P305+P351+P338
Chemistry & industry
Applications
DescriptionPF-06409577 is an activator of AMP-activated protein kinase (AMPK) heterotrimers (Kd = 9 nM for α1β1γ1). In vitro, it selectively activates β1-containing AMPK isoforms (EC50s = 2.18-7.03 nM) over β2-containing isoforms (EC50s = ≥10 μM). PF-06409577 has an EC50 value of 7 nM in an activation/protection TR-FRET assay using α1β1γ1 AMPK. In vivo, PF-06409577 (≥10 mg/kg) increases phosphorylation of AMPK in rat kidney. It decreases urinary albumin levels in a ZSF1 obese rat model of diabetes, metabolic syndrome, and renal disease when administered at a dose of 100 mg/kg.
UsesPF-06409577 has been used to determine its potential as a therapeutic agent for diabetic nephropathy.
General DescriptionPF-06409577 is a 6-chloro-indole derivative obtained from 5-bromo-6-chloro-indole.
Upstream & downstream products
Upstream raw materials
Related reactions
2 records
Compound notes
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