trifarotene   Click here for help

GtoPdb Ligand ID: 9962

Synonyms: Aklief® | CD5789 | compound 15b [PMID: 29706423]
Approved drug PDB Ligand Immunopharmacology Ligand
trifarotene is an approved drug (FDA (2019))
Compound class: Synthetic organic
Comment: Trifarotene (CD5789) is a RARγ-selective agonist that was developed as a topical anti-acne therapeutic [1-2,4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 70
Molecular weight 459.24
XLogP 7.16
No. Lipinski's rules broken 1
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Canonical SMILES OCCOc1ccc(cc1c1ccc(c(c1)C(C)(C)C)N1CCCC1)c1ccc(cc1)C(=O)O
Isomeric SMILES OCCOc1ccc(cc1c1ccc(c(c1)C(C)(C)C)N1CCCC1)c1ccc(cc1)C(=O)O
InChI InChI=1S/C29H33NO4/c1-29(2,3)25-19-23(10-12-26(25)30-14-4-5-15-30)24-18-22(11-13-27(24)34-17-16-31)20-6-8-21(9-7-20)28(32)33/h6-13,18-19,31H,4-5,14-17H2,1-3H3,(H,32,33)
Bioactivity Comments
The high metabolic instability of trifarotene (CD5789) suggests that it will exhibit limited systemic exposure when used as a topical agent.
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Retinoic acid receptor-γ Primary target of this compound Hs Agonist Agonist 8.1 pEC50 - 4
pEC50 8.1 (EC50 7.7x10-9 M) [4]
Description: Ligand-induced activation in a cellular reporter assay utlising the RARγ receptor ligand-binding domain.
Retinoic acid receptor-β Hs Agonist Agonist 6.9 pEC50 - 4
pEC50 6.9 (EC50 1.25x10-7 M) [4]
Description: In a reported assay measuring activation mediated by agonist binding to the RARβ ligand-binding domain.
Retinoic acid receptor-α Hs Agonist Agonist 6.3 pEC50 - 4
pEC50 6.3 (EC50 5x10-7 M) [4]
Description: In a reported assay measuring activation mediated by agonist binding to the RARα ligand-binding domain.