Prodrugs for transdermal drug delivery – trends and challenges

References

• Clas SD, Sanchez RI, Nofsinger R. Chemistry-enabled drug delivery (prodrugs): recent progress and challenges. Drug Discov Today 2014;19:79–87.
   PubMed Web of Science ®Google Scholar
• Liu KS, Hsieh PW, Aljuffali IA, et al. Impact of ester promoieties on transdermal delivery of ketorolac. J Pharm Sci 2014;103:974–86.
   PubMed Web of Science ®Google Scholar
• Ackaert OW, De Graan J, Capancioni R, et al. The in vitro and in vivo evaluation of new synthesized prodrugs of 5-OH-DPAT for iontophoretic delivery. J Control Release 2010;144:296–305.
   PubMed Web of Science ®Google Scholar
• Huttunen KM, Raunio H, Rautio J. Prodrugs – from serendipity to rational design. Pharmacol Rev 2011;63:750–71.
   PubMed Web of Science ®Google Scholar
• N'Da DD. Prodrug strategies for enhancing the percutaneous absorption of drugs. Molecules 2014;19:20780–807.
   PubMed Web of Science ®Google Scholar
• Sloan KB, Wasdo SC, Rautio J. Design for optimized topical delivery: prodrugs and a paradigm change. Pharm Res 2006;23:2729–47.
   PubMed Web of Science ®Google Scholar
• Stella VJ. Prodrugs: some thoughts and current issues. J Pharm Sci 2010;99:4755–65.
   PubMed Web of Science ®Google Scholar
• Sloan KB, Devarajan-Ketha H, Wasdo SC. Dermal and transdermal delivery: prodrugs. Ther Deliv 2011;2:83–105.
   PubMedGoogle Scholar
• Thomas JD, Majumdar S, Sloan KB. Soft alkyl ether prodrugs of a model phenolic drug: the effect of incorporation of ethyleneoxy groups on transdermal delivery. Molecules 2009;14:4231–45.
   PubMed Web of Science ®Google Scholar
• Ita K. Transdermal delivery of drugs with microneedles: strategies and outcomes. J Drug Deliv Sci Technol 2015;29:16–23.
   Web of Science ®Google Scholar
• Ita KB. Transdermal drug delivery: progress and challenges. J Drug Deliv Sci Technol 2014;24:245–50.
   Web of Science ®Google Scholar
• Ita KB, Popova IE. Influence of sonophoresis and chemical penetration enhancers on percutaneous transport of penbutolol sulfate. Pharm Dev Technol 2015. [Epub ahead of print]. DOI: 10.3109/10837450.2015.1086373.
   Web of Science ®Google Scholar
• Ita K. Transdermal delivery of drugs with microneedles – potential and challenges. Pharmaceutics 2015;7:90–105.
   PubMed Web of Science ®Google Scholar
• Vaddi HK, Banks SL, Chen J, et al. Human skin permeation of 3-O-alkyl carbamate prodrugs of naltrexone. J Pharm Sci 2009;98:2611–25.
   PubMed Web of Science ®Google Scholar
• Devarajan-Ketha H, Sloan KB. N,N'-dialkylaminoalkylcarbonyl (DAAC) prodrugs and aminoalkylcarbonyl (AAC) prodrugs of 4-hydroxyacetanilide and naltrexone with improved skin permeation properties. Bioorg Med Chem Lett 2011;21:4078–82.
   PubMed Web of Science ®Google Scholar
• Eldridge JA, Milewski M, Stinchcomb AL, Crooks PA. Synthesis and in vitro stability of amino acid prodrugs of 6-β-naltrexol for microneedle-enhanced transdermal delivery. Bioorg Med Chem Lett 2014;24:5212–15.
   PubMed Web of Science ®Google Scholar
• Florvall L, Fagervall I, Larsson L-G, Ross SB. Prodrugs of neuron-selective monoamine oxidase inhibitors: amino acid derivatives of 1-(4-aminophenyl)-2-aminopropanes. Eur J Med Chem 1999;34:137–51.
   Web of Science ®Google Scholar
• Ackaert OW, De Graan J, Shi S, et al. The pharmacokinetics and pharmacological effect of (S)-5-OH-DPAT following controlled delivery with transdermal iontophoresis. J Pharm Sci 2011;100:2996–3009.
   PubMed Web of Science ®Google Scholar
• Monene LM, Goosen C, Breytenbach JC, et al. Percutaneous absorption of cyclizine and its alkyl analogues. Eur J Pharm Sci 2005;24:239–44.
   PubMed Web of Science ®Google Scholar
• Imoto H, Zhou Z, Stinchcomb AL, Flynn GL. Transdermal prodrug concepts: permeation of buprenorphine and its alkyl esters through hairless mouse skin and influence of vehicles. Biol Pharm Bull 1996;19:263–7.
   PubMed Web of Science ®Google Scholar
• Gerber M, Breytenbach JC, du Plessis J. Transdermal penetration of zalcitabine, lamivudine and synthesised N-acyl lamivudine esters. Int J Pharm 2008;351:186–93.
   PubMed Web of Science ®Google Scholar
• Bijaya G, Kaushal D, Sonal D, Pallavi K. Synthesis and evaluation of esmolol prodrugs for transdermal delivery. Drug Deliv 2010;17:532–40.
   PubMed Web of Science ®Google Scholar
• Moss GP, Gullick DR, Cox PA, et al. Design, synthesis and characterization of captopril prodrugs for enhanced percutaneous absorption. J Pharm Pharmacol 2006;58:167–77.
   PubMed Web of Science ®Google Scholar
• Legoabe LJ, Breytenbach JC, N'Da DD, Breytenbach JW. Transdermal penetration of cytarabine and its 5'-O alkyl ester derivatives. Med Chem 2010;6:108–13.
   PubMed Web of Science ®Google Scholar
• Borkar N, Li B, Holm R, et al. Lipophilic prodrugs of apomorphine I: preparation, characterisation, and in vitro enzymatic hydrolysis in biorelevant media. Eur J Pharm Biopharm 2015;89:216–23.
   PubMed Web of Science ®Google Scholar
• Liu KS, Sung KC, Al-Suwayeh SA, et al. Enhancement of transdermal apomorphine delivery with a diester prodrug strategy. Eur J Pharm Biopharm 2011;78:422–31.
   PubMed Web of Science ®Google Scholar
• Hadgraft J. Skin deep. Eur J Pharm Biopharm 2004;58:291–9.
   PubMed Web of Science ®Google Scholar
• Swart H, Breytenbach JC, Hadgraft J, du Plessis J. Synthesis and transdermal penetration of NSAID glycoside esters. Int J Pharm 2005;301:71–9.
   PubMed Web of Science ®Google Scholar
• Ghosh I, Michniak-Kohn B. Influence of critical parameters of nanosuspension formulation on the permeability of a poorly soluble drug through the skin – a case study. AAPS PharmSciTech 2013;14:1108–17.
   PubMed Web of Science ®Google Scholar
• Majumdar S, Mueller-Spaeth M, Sloan KB. Prodrugs of theophylline incorporating ethyleneoxy groups in the promoiety: synthesis, characterization, and transdermal delivery. AAPS PharmSciTech 2012;13:853–62.
   PubMed Web of Science ®Google Scholar
• Kim BY, Doh HJ, Le TN, et al. Ketorolac amide prodrugs for transdermal delivery: stability and in vitro rat skin permeation studies. Int J Pharm 2005;293:193–202.
   PubMed Web of Science ®Google Scholar
• Yerramreddy TR, Milewski M, Penthala NR, et al. Novel 3-O-pegylated carboxylate and 3-O-pegylated carbamate prodrugs of naltrexone for microneedle-enhanced transdermal delivery. Bioorg Med Chem Lett 2010;20:3280–3.
   PubMed Web of Science ®Google Scholar
• Puglia C, Filosa R, Peduto A, et al. Evaluation of alternative strategies to optimize ketorolac transdermal delivery. AAPS PharmSciTech 2006;7:64.
   PubMed Web of Science ®Google Scholar
• Neumanova Z, Cerveny L, Ceckova M, Staud F. Role of ABCB1, ABCG2, ABCC2 and ABCC5 transporters in placental passage of zidovudine. Biopharm Drug Dispos 2016;37:28–38.
   PubMed Web of Science ®Google Scholar
• Barbi Mda S, Carvalho FC, Kiill CP, et al. Preparation and characterization of chitosan nanoparticles for zidovudine nasal delivery. J Nanosci Nanotechnol 2015;15:865–74.
   PubMed Web of Science ®Google Scholar
• N'Da D,D, Breytenbach JC. Synthesis of methoxypoly(ethylene glycol) carbonate prodrugs of zidovudine and penetration through human skin in vitro. J Pharm Pharmacol 2009;61:721–31.
   PubMed Web of Science ®Google Scholar
• Milewski M, Yerramreddy TR, Ghosh P, et al. In vitro permeation of a pegylated naltrexone prodrug across microneedle-treated skin. J Control Release 2010;146:37–44.
   PubMed Web of Science ®Google Scholar
• Hayton WL, Chen T. Correction of perfusate concentration for sample removal. J Pharm Sci 1982;71:820–1.
   Google Scholar
• Gannu R, Palem CR, Yamsani SK, et al. Enhanced bioavailability of buspirone from reservoir-based transdermal therapeutic system, optimization of formulation employing Box–Behnken statistical design. AAPS PharmSciTech 2010;11:976–85.
   PubMed Web of Science ®Google Scholar
• Hoang MT, Ita KB, Bair DA. Solid microneedles for transdermal delivery of amantadine hydrochloride and pramipexole dihydrochloride. Pharmaceutics 2015;7:379–96.
   PubMed Web of Science ®Google Scholar
• Ita K. Transdermal iontophoretic drug delivery: advances and challenges. J Drug Target 2015. [Epub ahead of print]. DOI: 10.3109/1061186X.2015.1090442.
   PubMed Web of Science ®Google Scholar
• Paudel KS, Nalluri BN, Hammell DC, et al. Transdermal delivery of naltrexone and its active metabolite 6-beta-naltrexol in human skin in vitro and guinea pigs in vivo. J Pharm Sci 2005;94:1965–75.
   PubMed Web of Science ®Google Scholar
• Thiollet M, Funck-Brentano C, Grange JD, et al. The pharmacokinetics of perindopril in patients with liver cirrhosis. Br J Clin Pharmacol 1992;33:326–8.
   PubMed Web of Science ®Google Scholar
• Sennesael J, Ali A, Sweny P, et al. The pharmacokinetics of perindopril and its effects on serum angiotensin converting enzyme activity in hypertensive patients with chronic renal failure. Br J Clin Pharmacol 1992;33:93–9.
   PubMed Web of Science ®Google Scholar