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KI1048Adapalene25 mg$154
Adapalene50 mg$272

Chemical Characteristic

Product NameAdapalene
SynonymsDifferin
CAS No.106685-40-9
Molecular Weight 412.52
FormulaC28H28O3
Chemical Name6-[3-(1-Adamantyl)-4-methoxy-phenyl]naphthalene-2-carboxylic acid
Smilesc1c(ccc2cc(ccc12)c1cc(c(cc1)OC)C12CC3CC(CC(C1)C3)C2)C(=O)O
Chemical Structure

Biological activities

Adapalene is a third-generation topical retinoid. Adapalene is primarily used in the treatment of mild-moderate acne and is also used (off-label) to treat keratosis pilaris as well as other skin conditions.[1] Adapalene has higher affinity for RARβ and RARγ than for RARα. The AC50 values for the transactivation potential of adapalene against RARα, RARβ and RARγ is 22, 2.3 and 9.3 nM, respectively. The Kd values of adapalene for human RAR subtypes RARα, RARβ and RARγ is 1100, 34 and 130 nM, respectively. In vitro, adapalene inhibits the proliferation of HeLa cells with an IC50 of 16 nM and inhibits the differentiation of F9 cells with an AC50 of 40 nM. Adapalene also induces differentiation of mouse embryonal carcinoma cells and inhibits keratinocyte transglutaminase in vitro. Adapalene is able to modify epidermal morphogenesis and keratinocyte differentiation in a reconstructed skin model. In rhino mouse model of comedolysis in vivo, topical adapalene reduces number of epidermal comedones and increases epidermal thickness.[2]

Protocols

In vitro: Adapalene is dissolved in DMSO.[2]

References

[1] Rolewski SL, et al. Clinical review: topical retinoids. Dermatol Nurs. 2003, 15(5): 447-450, 459-465.
[2] Shroot B, et al. Pharmacology and chemistry of adapalene. J Am Acad Dermatol. 1997, 36(6 Pt 2): S96-103.

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