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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 of FK-614

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
FK614, a novel peroxisome proliferator-activated receptor gamma modulator, induces differential transactivation through a unique ligand-specific interaction with transcriptional coactivators.
2005 Dec
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
Ameliorating effect of FK614, a novel nonthiazolidinedione peroxisome proliferator-activated receptor gamma agonist, on insulin resistance in Zucker fatty rat.
2005 Sep 5
A selective peroxisome proliferator-activated receptor gamma modulator with distinct fat cell regulation properties.
2006 Aug
Unique properties of coactivator recruitment caused by differential binding of FK614, an anti-diabetic agent, to peroxisome proliferator-activated receptor gamma.
2006 Mar
Patents

Patents

Sample Use Guides

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 GMT 2023
Edited
by admin
on Fri Dec 15 15:38:50 GMT 2023
Record UNII
V5Q32BZX79
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Fri Dec 15 15:38:50 GMT 2023 , Edited by admin on Fri Dec 15 15:38:50 GMT 2023
PRIMARY
PUBCHEM
9869229
Created by admin on Fri Dec 15 15:38:50 GMT 2023 , Edited by admin on Fri Dec 15 15:38:50 GMT 2023
PRIMARY
DRUG BANK
DB12557
Created by admin on Fri Dec 15 15:38:50 GMT 2023 , Edited by admin on Fri Dec 15 15:38:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID60940978
Created by admin on Fri Dec 15 15:38:50 GMT 2023 , Edited by admin on Fri Dec 15 15:38:50 GMT 2023
PRIMARY
CAS
193012-35-0
Created by admin on Fri Dec 15 15:38:50 GMT 2023 , Edited by admin on Fri Dec 15 15:38:50 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY