U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

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
Record UNII
V5Q32BZX79
Record Status Validated (UNII)
Record Version