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)
1. Aubert J, Piwnica D, Bertino B, Blanchet-Réthoré S, Carlavan I, Déret S, Dreno B, Gamboa B, Jomard A, Luzy AP et al.. (2018)
Nonclinical and human pharmacology of the potent and selective topical retinoic acid receptor-γ agonist trifarotene.
Br J Dermatol, 179 (2): 442-456. [PMID:29974453]
2. Balak DMW. (2018)
Topical trifarotene: a new retinoid.
Br J Dermatol, 179 (2): 231-232. [PMID:30141539]
3. Blume-Peytavi U, Fowler J, Kemény L, Draelos Z, Cook-Bolden F, Dirschka T, Eichenfield L, Graeber M, Ahmad F, Alió Saenz A et al.. (2020)
Long-term safety and efficacy of trifarotene 50 μg/g cream, a first-in-class RAR-γ selective topical retinoid, in patients with moderate facial and truncal acne.
J Eur Acad Dermatol Venereol, 34 (1): 166-173. [PMID:31306527]
4. Thoreau E, Arlabosse JM, Bouix-Peter C, Chambon S, Chantalat L, Daver S, Dumais L, Duvert G, Feret A, Ouvry G et al.. (2018)
Structure-based design of Trifarotene (CD5789), a potent and selective RARγ agonist for the treatment of acne.
Bioorg Med Chem Lett, 28 (10): 1736-1741. [PMID:29706423]