obeticholic acid

Ligand id: 3435

Name: obeticholic acid

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 77.76
Molecular weight 420.32
XLogP 7.04
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

No information available.
Summary of Clinical Use
In March 2014 the EMA granted orphan designation for obeticholic acid for the treatment of primary sclerosing cholangitis. Also in 2014, the US FDA granted Fast Track designation to obeticholic acid (OCA) for the treatment of primary biliary cirrhosis. The Fast Track programme is intended to expedite the development, review and potential approval of drugs which treat serious conditions and fill an unmet medical need. In May 2016, the US FDA granted full marketing authorisation for obeticholic acid to be used for the treatment of primary biliary cholangitis.
Mechanism Of Action and Pharmacodynamic Effects
Obeticholic acid is a farnesoid X receptor (FXR) agonist which has anticholestatic activity in an in vivo rat model of cholestasis [3]. FXR is a nuclear receptor for bile acids [2] and is important for the regulation of expression of target genes involved in bile acid and cholesterol homeostasis. Ligand activation of FXR has two noteworthy effects; repression of the production of bile acid biosynthetic enzymes and enhanced expression of proteins involved in bile acid transport. These effects account for the compound's anticholestatic activity [1].