Isolation and characterisation of impurities in adapalene.
ABSTRACT Three impurities of structure 2-4 were isolated and characterised during the optimisation of a synthetic procedure to adapalene. Impurity 1 was a by-product of the Friedel-Crafts reaction of adamantanol with 4-bromoanisole. Impurities 3 and 4 were due to side reactions of the final Negishi coupling.
Article: Spotlight on adapalene.[show abstract] [hide abstract]
ABSTRACT: In the field of dermatology, topical retinoids represent a mainstay in acne treatment. Adapalene is a naphthoic acid derivative showing some pharmacological activities similar to the regular retinoids. The drug is used singly or in combination for treating acne and a few other miscellaneous skin disorders. To critically review the pharmacokinetic, pharmacologic aspects and clinical benefits and adverse effects associated with topical adapalene. A systematic literature review was conducted primarily based on PubMed citations. Adapalene shares some biological activities in common with retinoic acid. However, it exhibits distinct physicochemical and binding properties for selective retinoic acid receptors. In acne, adapalene is expected to reduce comedogenesis, expel mature comedones and exert some anti-inflammatory effects. The drug is effective as monotherapy in mild comedonal acne and in combination with benzoyl peroxide for mild-to-moderate inflammatory acne. The safety profile of adapalene is good. Indeed, only discrete to moderate adverse events including erytheme, xerosis, itching and stinging may develop during the early treatment phase. Clinical experience has established that adapalene represents a valuable addition to the other current treatments for acne.Expert Opinion on Drug Metabolism & Toxicology 12/2009; 5(12):1565-75. · 2.94 Impact Factor