| Stereochemistry | ACHIRAL |
| Molecular Formula | C25H24F2N2O3 |
| Molecular Weight | 438.4665 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)OC(=O)C1=CN(CC(C)(C)C2=C1NC3=C2C=CC=C3)C(=O)C4=CC=C(F)C(F)=C4
InChI
InChIKey=INASOKQDNHHMRE-UHFFFAOYSA-N
InChI=1S/C25H24F2N2O3/c1-14(2)32-24(31)17-12-29(23(30)15-9-10-18(26)19(27)11-15)13-25(3,4)21-16-7-5-6-8-20(16)28-22(17)21/h5-12,14,28H,13H2,1-4H3
Turofexorate Isopropyl (XL335) is a potent, selective, and orally bioavailable FXR agonist. Binds to the ligand-binding domain (LBD) of human FXR. Turofexorate Isopropyl resides in a predominately hydrophobic pocket with only a few polar atoms making contact with WAY-362450. Turofexorate Isopropyl promotes transcription of the human BSEP, human SHP, and mouse IBABP genes utilizing reporter constructs with EC50 of 17, 230, and 33 nM, respectively in promoter assays. Turofexorate Isopropyl had been in phase I clinical trials for the treatment of hyperlipidemia. This compound was originally discovered by Exelixis Pharmaceuticals, then licensed to Wyeth (now a wholly-owned subsidiary of Pfizer). However, the studies were discontinued.
Originator
Approval Year
Sourcing
PubMed
Sample Use Guides
Turofexorate Isopropyl (WAY-362450) at concentration of 1 μM significantly induces mRNAs encoding for BSEP, SHP, and IBABP in human cell cultures to 13-, 2-, and 20-fold, respectively. Turofexorate Isopropyl at concentration of 1 uM suppresses interleukin-6-induced CRP expression in human Hep3B hepatoma cells, and the inhibitory effect is attenuated when knockdown of FXR by short interfering RNA.
ACTIVE MOIETY
