FK-614

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H23Cl2N3O3S
Molecular Weight	468.397
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCS(=O)(=O)NC(=O)C1=CC2=C(C=C1)N=C(C)N2CC3=CC=C(Cl)C=C3Cl

InChI

InChIKey=UYGZODVVDUIDDQ-UHFFFAOYSA-N

InChI=1S/C21H23Cl2N3O3S/c1-3-4-5-10-30(28,29)25-21(27)15-7-9-19-20(11-15)26(14(2)24-19)13-16-6-8-17(22)12-18(16)23/h6-9,11-12H,3-5,10,13H2,1-2H3,(H,25,27)

HIDE SMILES / InChI

Molecular Formula	C21H23Cl2N3O3S
Molecular Weight	468.397
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/67496142 | https://www.businesswire.com/news/home/20100628005490/en/Aestus-Therapeutics-Astellas-Pharma-Sign-License-Deal | https://www.ncbi.nlm.nih.gov/pubmed/16682454

FK-614, a benzimidazole derivative without a thiazolidinedione structure, is a selective peroxisome proliferator-activated receptor gamma agonist. It is a diabetes drug candidate that found implication in pain, including post-herpetic neuralgia.

Originator

Approval Year

PubMed

Title	Date	PubMed
FK614, a novel peroxisome proliferator-activated receptor gamma modulator, induces differential transactivation through a unique ligand-specific interaction with transcriptional coactivators.	2005 Dec	16314690
FK-614, a selective peroxisome proliferator-activated receptor gamma agonist, improves peripheral glucose utilization while decreasing hepatic insulin extraction in alloxan-induced diabetic dogs.	2005 Sep	16125538
Ameliorating effect of FK614, a novel nonthiazolidinedione peroxisome proliferator-activated receptor gamma agonist, on insulin resistance in Zucker fatty rat.	2005 Sep 5	16039648
A selective peroxisome proliferator-activated receptor gamma modulator with distinct fat cell regulation properties.	2006 Aug	16682454
Unique properties of coactivator recruitment caused by differential binding of FK614, an anti-diabetic agent, to peroxisome proliferator-activated receptor gamma.	2006 Mar	16508139

Patents

Sample Use Guides

In Vitro Use Guide

FK-614, rosiglitazone, and pioglitazone competed for specific binding of [3H]rosiglitazone to peroxisome proliferator-activated receptor gamma (PPARgamma) with Ki values of 11 nM, 47 nM, and 1.3 microM, respectively. K614 induced interaction of PPARgamma with nuclear receptor coactivator CBP but of lower magnitude than rosiglitazone and pioglitazone. The estimated Kd values of FK614-, rosiglitazone-, and pioglitazone-PPARgamma complex to CBP peptide were 1.8, 0.64, and 0.72 microM, respectively, indicating FK-614/PPARgamma complex exhibits a lower affinity for CBP peptide compared to other agonist-PPARgamma complexes.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:38:50 UTC 2023` Edited by `admin` on `Fri Dec 15 15:38:50 UTC 2023`
Record UNII	V5Q32BZX79
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FK-614

Common Name

English

FK614

Code

English

1-(2,4-DICHLOROBENZYL)-2-METHYL-6-(1-PENTANESULFONYLCARBAMOYL)BENZIMIDAZOLE

Systematic Name

English

3-(2,4-DICHLOROBENZYL)-2-METHYL-N-(PENTYLSULFONYL)-3H-BENZIMIDAZOLE-5-CARBOXAMIDE

Systematic Name

English

Code System Code Type Description

FDA UNII

V5Q32BZX79