adapalene   

GtoPdb Ligand ID: 5429

Synonyms: Differin®
adapalene is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Adapalene is a third-generation topical anti-acne retinoid.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 46.53
Molecular weight 412.2
XLogP 8.57
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES COc1ccc(cc1C12CC3CC(C2)CC(C1)C3)c1ccc2c(c1)ccc(c2)C(=O)O
Isomeric SMILES COc1ccc(cc1C12CC3CC(C2)CC(C1)C3)c1ccc2c(c1)ccc(c2)C(=O)O
InChI InChI=1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30)
InChI Key LZCDAPDGXCYOEH-UHFFFAOYSA-N
Bioactivity Comments
Adapalene is selective for the β and γ RARs over the α isoform [1].
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Retinoic acid receptor-β Hs Agonist Agonist 7.5 pKi - 1
pKi 7.5 (Ki 3.4x10-8 M) [1]
Description: Binding affinity to RARβ using [3H]CD 367 as radioligand.
Retinoic acid receptor-γ Hs Agonist Agonist 6.9 pKi - 1
pKi 6.9 (Ki 1.3x10-7 M) [1]
Description: Binding affinity to RARγ using [3H]CD 367 as radioligand.
Retinoic acid receptor-α Hs Agonist Agonist 6.0 pKi - 1
pKi 6.0 (Ki 1.1x10-6 M) [1]
Description: Binding affinity to RARα using [3H]CD 367 as radioligand.
Ligand mentioned in the following text fields