cilofexor   Click here for help

GtoPdb Ligand ID: 10644

Synonyms: example 13/9 [US10485795B2] | GS-9674 | GS9674
PDB Ligand
Compound class: Synthetic organic
Comment: Cilofexor (GS-9674) is a nonsteroidal farnesoid X receptor (FXR) agonist. It was originally identified by Phenex Pharmaceuticals [1] and is being developed by Gilead Pharmaceuticals for hepatic anti-steatotic activity, and potential to treat nonalcoholic fatty liver disease (NAFLD) and/or nonalcoholic steatohepatitis (NASH). Successful treatment of these liver conditions will most likely be achieved using combinations of antilipemic, anti-inflammatory and anti-fibrotic agents.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 108.92
Molecular weight 585.06
XLogP 6.49
No. Lipinski's rules broken 1
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Canonical SMILES OC(=O)c1ccnc(c1)N1CC(C1)(O)c1ccc(cc1Cl)OCc1c(onc1c1c(Cl)cccc1Cl)C1CC1
Isomeric SMILES OC(=O)c1ccnc(c1)N1CC(C1)(O)c1ccc(cc1Cl)OCc1c(onc1c1c(Cl)cccc1Cl)C1CC1
InChI InChI=1S/C28H22Cl3N3O5/c29-20-2-1-3-21(30)24(20)25-18(26(39-33-25)15-4-5-15)12-38-17-6-7-19(22(31)11-17)28(37)13-34(14-28)23-10-16(27(35)36)8-9-32-23/h1-3,6-11,15,37H,4-5,12-14H2,(H,35,36)
1. Kinzel O, Steeneck C, Kremoser C. (2013)
Novel fxr (nr1h4) binding and activity modulating compounds.
Patent number: WO2013007387. Assignee: Phenex Pharmaceuticals. Priority date: 13/07/2011. Publication date: 17/01/2013.
2. Kinzel O, Steeneck C, Kremoser C. (2019)
FXR (NR1H4) binding and activity modulating compounds.
Patent number: US10485795B2. Assignee: Gilead Sciences Inc. Priority date: 13/07/2011. Publication date: 26/11/2019.
3. Trauner M, Gulamhusein A, Hameed B, Caldwell S, Shiffman ML, Landis C, Eksteen B, Agarwal K, Muir A, Rushbrook S et al.. (2019)
The Nonsteroidal Farnesoid X Receptor Agonist Cilofexor (GS-9674) Improves Markers of Cholestasis and Liver Injury in Patients With Primary Sclerosing Cholangitis.
Hepatology, 70 (3): 788-801. [PMID:30661255]