Adapalene is a third-generation topical retinoid primarily used for the treatment of mild to moderate acne. It is also used off-label for conditions like keratosis pilaris. Adapalene is known for its efficacy comparable to other retinoids but with a superior safety profile, causing less irritation. The molecule is chemically stable, allowing it to be used in combination with benzoyl peroxide without concerns of photodegradation.
Adapalene functions by binding to nuclear retinoic acid receptors, specifically RAR-beta and RAR-gamma, which modulate gene transcription and affect keratinocyte proliferation and differentiation. This leads to a reduction in microcomedone formation, decreased pore clogging, and increased exfoliation. Additionally, adapalene exhibits anti-inflammatory properties by suppressing the inflammatory response triggered by Cutibacterium acnes and inhibiting lipoxygenase activity.
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| Other Names | Differin |
|---|---|
| IUPAC Name | 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid |
| CAS | 106685-40-9 |
| Molecular Weight | 412.5 |
| Molecular Formula | C28H28O3 |
| SMILES | COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)O)C45CC6CC(C4)CC(C6)C5 |