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Formulation, in Vitro Release and Transdermal Diffusion of Selected Retinoids

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Formulation, in Vitro Release and Transdermal Diffusion of Selected Retinoids Formulation, in vitro release and transdermal diffusion of selected retinoids Arina Krüger (B.Pharm.) Dissertation submitted in the partial fulfilment of the requirements for the degree Magister Scientiae in Pharmaceutics at the Potchefstroom Campus of the North-West University Supervisor: Prof. J. du Plessis Co-supervisor: Dr. J. Viljoen Assistant-supervisor: Dr. M.M. Malan November 2010 This dissertation is presented in the so-called article format, which includes introductory chapters, a full length article for publication in a pharmaceutical journal and appendices containing relevant experimental data. The article contained in this dissertation is to be published in the International Journal of Pharmaceutics of which the complete guide for authors is included in appendix F. Abstract Acne is a multifactorial skin disease affecting about 80 % of people aged 11 to 30. Several systemic and topical treatments are used to treat existing lesions, prevent scarring and suppress the development of new lesions. Topical therapy is often used as first line treatment for acne, due to the location of the target organ, the pilosebaceous unit, in the skin. Retinoids are widely used as oral or topical treatment for this disease, with tretinoin and adapalene being two of the most used topical retinoids. The transdermal route offers several challenges to drug delivery, e.g. the excellent resistance of the stratum corneum to diffusion, as well as variable skin properties such as site, age, race and disease. Some additional difficulties are associated with the dermatological delivery of tretinoin and adapalene, which include suboptimal water solubility of the retinoids, isomerisation of tretinoin in the skin, mild to severe skin irritation, as well as oxidation and photo-isomerisation of tretinoin, even before crossing the stratum corneum. Researchers constantly strive to improve dermatological retinoid formulations in order to combat low dermal flux, skin irritation and instability. The release kinetics of tretinoin varies greatly according to the way in which it is incorporated into the formulation and according to the type of formulation used. Little research has been conducted regarding improved formulations for adapalene. Pheroid™ technology is a patented delivery system employed in this study in order to improve the dermal delivery of retinoids. Tretinoin and adapalene were separately incorporated into castor oil, vitamin F and Pheroid™ creams. The creams were evaluated in terms of their in vitro retinoid release, in vitro transdermal diffusion and stability. Castor oil and Pheroid™ creams were superior in terms of release and dermal delivery of adapalene. Tretinoin was best released and delivered to the dermis by castor oil cream. The castor oil creams were the most stable formulations, whereas the Pheroid™ creams were the most unstable. In terms of release, dermal diffusion and stability, castor oil cream proved to be the most suitable cream for both tretinoin and adapalene. Keywords: Tretinoin, Adapalene, Dermal delivery, Pheroid™, Castor oil, Vitamin F, Stability i Opsomming Aknee is ’n velsiekte met veelvoudige oorsake wat ongeveer 80 % van persone tussen die ouderdom van 11 en 30 affekteer. Verskeie sistemiese en topikale behandelings word gebruik om bestaande letsels te behandel, littekens te voorkom en die ontwikkeling van nuwe letsels te onderdruk. Topikale behandeling word dikwels as eerste linie gebruik om aknee te behandel weens die ligging van die teikenorgaan, die trigotalg-eenheid, in die vel. Retinoïede word algemeen as orale of topikale behandeling vir hierdie siekte gebruik. Tretinoïen en adapaleen is twee van die mees gebruikte topikale retinoïede. Die transdermale weg stel verskeie uitdagings vir die aflewering van geneesmiddels, bv. die uitstekende weerstand wat die stratum corneum teen diffusie bied, asook veranderlike eienskappe van die vel soos plek, ouderdom, ras en siektetoestand. Bykomende probleme word met dermatologiese aflewering van tretinoïen en adapaleen in verband gebring en sluit die volgende in: onvoldoende wateroplosbaarheid van die retinoïede, isomerisasie van tretinoïen in die vel, matige tot erge velirritasie, en oksidering en foto-isomerisasie van tretinoïen, selfs voor dit die stratum corneum oorsteek. Navorsers poog gedurig om dermatologiese retinoïed-formulerings te verbeter om sodoende lae dermale fluksie, velirritasie en onstabiliteit te bekamp. Die kinetika van vrystelling van tretinoïen wissel baie na gelang van die manier waarin dit in die formulering geïnkorporeer is, asook van die tipe formulering wat gebruik is. Min navorsing aangaande verbeterde formulerings vir adapaleen is al uitgevoer. Pheroid™-tegnologie is ’n gepatenteerde afleweringsisteem wat in hierdie studie gebruik is om die dermale aflewering van retinoïede te verbeter. Tretinoïen en adapaleen is afsonderlik in kasterolie-, vitamien F- en Pheroid™-rome geïnkorporeer. Die rome is geëvalueer in terme van hul in vitro retinoïedvrystelling en transdermale diffusie, asook stabiliteit. Die kasterolie- en Pheroid™-rome was beduidend beter in terme van vrystelling en dermale aflewering van adapaleen. Tretinoïen is die beste vrygestel en in die dermis afgelewer deur kasterolieroom. Die kasterolierome was die mees stabiele formulerings, terwyl die Pheroid™- rome die onstabielste was. In terme van vrystelling, dermale diffusie en stabiliteit was kasterolieroom die geskikste room vir beide tretinoïn en adapaleen. Sleutelwoorde: Tretinoïen, Adapaleen, Dermale aflewering, Pheroid™, Kasterolie, Vitamien F, Stabiliteit ii Acknowledgements From Him and through Him and for Him are all things. To Him be the glory forever! (Rom. 11:36) Soli Deo Gloria! I wish to express my gratitude to the following people: • My parents, for giving me the opportunity to further my education. Thank you for your unceasing love and support and for helping me to stay focused. • My grandparents, brothers and sisters-in-law, for their interest in my study and for their motivation and support. • My friends and colleagues, for their friendship and encouragement. • My supervisor, Prof. Jeanetta du Plessis, for her skilled advice, guidance and help during the course of this study. • Drs. Joe Viljoen and Maides Malan, for their time and helpful suggestions. • Prof. Jan du Preez, for his assistance with the development of the HPLC methods and for general good advice regarding my study. • Dr. Minja Gerber, for her help, guidance and advice throughout the study. • Ms. Hester de Beer, for assisting with the administrative part of this study. • Liezl-Marie Nieuwoudt, for her assistance with the formulation of the Pheroid™ creams. • Prof. Jan du Plessis, for the statistical analysis of the data. • Karen Krüger, for proofreading this work. • The National Research Foundation (NRF) and the Unit for Drug Research and Development, North-West University, for financial support. iii Table of contents Abstract ......................................................................................................................................... i Opsomming ................................................................................................................................. ii Acknowledgements ....................................................................................................................iii List of figures .............................................................................................................................vii List of tables ............................................................................................................................. viii Chapter 1: Introduction and problem statement ..................................................................... 1 Chapter 2: Dermal delivery of retinoids for the treatment of acne ........................................ 5 2.1 Introduction ..................................................................................................................... 5 2.2 The skin .......................................................................................................................... 5 2.3 The pilosebaceous unit .................................................................................................. 6 2.4 Acne ............................................................................................................................... 8 2.4.1 Pathophysiology .................................................................................................... 8 2.4.2 Treatments .......................................................................................................... 10 2.4.2.1 Topical treatments ........................................................................................ 12 2.4.2.2 Systemic treatments ..................................................................................... 13 2.4.2.3 Adjunctive drug treatments .......................................................................... 14 2.4.2.4 Non-drug treatments .................................................................................... 14 2.4.3 Patient education ................................................................................................ 14 2.5 Retinoids ...................................................................................................................... 15 2.5.1 Background ......................................................................................................... 15 2.5.2 In vivo functions .................................................................................................
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