chenodeoxycholic acid   Click here for help

GtoPdb Ligand ID: 608

Abbreviated name: CDCA
Synonyms: Chenix® | chenodeoxycholate | Chenodiol® | Leadiant® (formerly Chenodeoxycholic acid sigma-tau)
Approved drug PDB Ligand
chenodeoxycholic acid is an approved drug (FDA (1983), EMA (2017))
Comment: Farnesoid X receptor (bile acid receptor FXR) agonist
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 77.76
Molecular weight 392.29
XLogP 6.18
No. Lipinski's rules broken 1
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Isomeric SMILES O[C@@H]1CC[C@]2([C@@H](C1)C[C@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)O)C)C)O)C
InChI InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1
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Summary of Clinical Use Click here for help
Used to treat certain types of gall stones in patients where surgery is not an option. Chenodeoxycholic acid Leadiant® is EMA approved as a replacement therapy for patients with cerebrotendinous xanthomatosis, a disease in which genetic abnormalities in the gene for the liver enzyme sterol 27 hydroxylase (CYP27A1) mean that inadequate amounts of the primary bile acid chenodeoxycholic acid are produced.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
May directly influence synthesis and transport of bile acids via interaction with the bile acid receptor, FXR (farnesoid X receptor). The net effect of chenodeoxycholic acid is to reduce cholesterol and cholic acid synthesis in the liver thus reducing the biliary load of stone forming compounds.