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.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: adapalene

2D Structure
Click here for structure editor
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
No information available.
Summary of Clinical Use
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
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.