adapalene   Click here for help

GtoPdb Ligand ID: 5429

Synonyms: Differin®
Approved drug
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
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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
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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)
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Summary of Clinical Use Click here for help
Adapalene is a retinoid, applied topically to treat acne.
As of July 2016, a 0.1% adapalene gel has FDA approval as the first retinoid available for over-the-counter sales.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Activation of nuclear retinoic acid receptors (RARβ and γ) is believed to reduce the pore blockage that causes acne lesions. This effect is achieved through normalisation of the differentiation of follicular cells in the epithelium, which may be aberrant in the pathogenesis of acne.