Effect of O-acylmenthol and salt formation on the skin permeation of diclofenac acid

References

• Menassé R, Hedwall PR, Kraetz J, Pericin C, Riesterer L, Sallmann A, (1978). Pharmacological properties of diclofenac sodium and its metabolites. Scand J Rheumatol, 22(Suppl.):5–16.
   Google Scholar
• Fini A, Fazio G, Rapaport I. (1993). Diclofenac/N-(2-hydroxyethyl) pyrrolidine: A new salt for an old drug. Drugs Exp Clin Res, XIX:81–8.
   Google Scholar
• Hadgraft J. (1999). Passive enhancement strategies in topical and transdermal drug delivery. Int J Pharm, 184:1–6.
   PubMed Web of Science ®Google Scholar
• Zhao L, Fang L, Xu Y, Liu S, He Z, Zhao Y. (2008). Effect of O-acylmenthol on transdermal delivery of drugs with different lipophilicity. Int J Pharm, 352:92–103.
   PubMed Web of Science ®Google Scholar
• Zhao L, Fang L, Xu Y, Zhao Y, He Z. (2008). Transdermal delivery of penetrants with differing lipophilicities using O-acylmenthol derivatives as penetration enhancers. Eur J Pharm Biopharm, 69:199–213.
   PubMed Web of Science ®Google Scholar
• Montagna W. (1955). Histology and cytochemistry of human skin: IX. The distribution of non-specific esterases. J Biophys Biochem Cyol, 1:13–6.
   PubMedGoogle Scholar
• Hrabálek A, Dolež;al P, Vávrová K, Zbytovská J, Holas T, Klimentová J, (2006). Synthesis and enhancing effect of transkarbam 12 on the transdermal delivery of theophylline, clotrimazole, flobufen, and griseofulvin. Pharm Res, 23:912–9.
   PubMed Web of Science ®Google Scholar
• Vávrová K, Hrabálek A, Doležal P, Holas T, Klimentová J. (2005). Biodegradable derivatives of tranexamic acid as transdermal permeation enhancers. J Control Release, 104:41–9.
   PubMed Web of Science ®Google Scholar
• Castellari C, Ottani S. (1996). Diclofenac salts IV. Tris(2-hysroxyethyl)-ammonium-2-(2,6-dichlorophenylamino)-phenylacetate. Acta Crystallogr C, 52:2619–22.
   Web of Science ®Google Scholar
• Castellari C. (1995). Anti-inflammatory drugs. II. Salt of 2-(2,6-dichlorophenylamino)phenylacetic acid with diethanolamine. Acta Crystallogr C, 51:2612–15.
   Web of Science ®Google Scholar
• Castellari C, Sabatino P. (1994). Anti-inflammatory drugs: 1-(2-hydroxyethyl) pyrrolidinium salt of diclofenac. Acta Crystallogr C, 50:1723–26.
   PubMed Web of Science ®Google Scholar
• Megwa SA, Cross SE, Benson HA, Roberts MS. (2000). Ion-pair formation as a strategy to enhance topical delivery of salicylic acid. J Pharm Pharmacol, 52:919–28.
   PubMed Web of Science ®Google Scholar
• Nash RA, Mehta DB, Matias JR, Orentreich N. (1992). The possibility of lidocaine ion pair absorption through excised hair-less mouse skin. Skin Pharmacol, 5:160–70.
   PubMedGoogle Scholar
• Fini A, Fazio G, Gonzalez-Rodriguez M, Cavallari C, Passerini N, Rodriguez L. (1999). Formation of ion-pairs in aqueous solutions of diclofenac salts. Int J Pharm, 187:163–73.
   PubMed Web of Science ®Google Scholar
• Kamal MM, Iimura N, Nabekura T, Kitagawa S. (2006). Enhanced skin permeation of salicylate by ion-pair formation in non-aqueous vehicle and further enhancement by ethanol and l-menthol. Chem Pharm Bull, 54:481–4.
   PubMed Web of Science ®Google Scholar
• Kamal MM, Iimura N, Nabekura T, Kitagawa S. (2007). Enhanced skin permeation of diclofenac by ion-pair formation and further enhancement by microemulsion. Chem Pharm Bull, 55:368–71.
   PubMed Web of Science ®Google Scholar
• Megwa SA, Cross SE, Whitehouse MW, Benson HA, Roberts MS. (2000). Effect of ion pairing with alkylamines on the in-vitro dermal penetration and local tissue disposition of salicylates. J Pharm Pharmacol, 52:929–40.
   PubMed Web of Science ®Google Scholar
• Minghetti P, Cilurzo F, Casiraghi A, Montanari L, Fini A. (2007). Ex vivo study of transdermal permeation of four diclofenac salts from different vehicles. J Pharm Sci, 96:814–23.
   PubMed Web of Science ®Google Scholar
• Narishetty STK, Panchagnula R. (2004). Transdermal delivery of zidovudine: Effect of terpenes and their mechanism of action. J Control Release, 95:367–79.
   PubMed Web of Science ®Google Scholar
• Fang L, Kobayashi Y, Numajiri S, Kobayashi D, Sugibayashi K, Morimoto Y. (2002). The enhancing effect of a triethanolamine-ethanol-isopropyl myristate mixed system on the skin permeation of acidic drugs. Biol Pharm Bull, 25:1339–44.
   PubMed Web of Science ®Google Scholar
• Niazy EM. (1996). Differences in penetration-enhancing effect of azone through excised rabbit, rat, hairless mouse, guinea pig and human skins. Int J Pharm, 130:225–30.
   Web of Science ®Google Scholar
• Scheuplein RJ. (1978). Site variations in diffusion and permeability. In: Jarret A, ed. The physiology and pathophysiology of skin. New York: Academic Press, 1693–730.
   Google Scholar
• Cavallari C, Rodriguez L, Albertini B, Passerini N, Rosetti F, Fini A. (2005). Thermal and fractal analysis of diclofenac/gelucire 50/13 microparticles obtained by ultrasound-assisted atomization. J Pharm Sci, 94:1124–34.
   PubMed Web of Science ®Google Scholar
• Fini A, Fazio G, Benetti L, Ghedini V. (2007). Diclofenac salts. IV. Thermal analysis of some diclofenac salts with alkyl and alkylhydroxy amines. Thermochim Acta, 464:65–74.
   Web of Science ®Google Scholar
• Fini A, Garuti M, Fazio G, Alvarez-Fuentes J, Holgado MA. (2001). Diclofenac salts. I. Fractal and thermal analysis of sodium and potassium diclofenac salts. J Pharm Sci, 90:2049–57.
   PubMed Web of Science ®Google Scholar
• O'Connor KM, Corrigan OI. (2001). Comparison of the physicochemical properties of the N-(2-hydroxyethyl) pyrrolidine, diethylamine and sodium salt forms of diclofenac. Int J Pharm, 222:281–93.
   PubMed Web of Science ®Google Scholar
• Lee PJ, Ahmad N, Langer R, Mitragotri S, Shastri VP. (2006). Evaluation of chemical enhancers in the transdermal delivery of lidocaine. Int J Pharm, 308:33–9.
   PubMed Web of Science ®Google Scholar
• Leichtnam ML, Rolland H, Wüthrich P, Guy RH. (2006). Identification of penetration enhancers for testosterone transdermal delivery from spray formulations. J Control Release, 113:57–62.
   PubMed Web of Science ®Google Scholar
• Singh BN, Singh RB, Singh J. (2005). Effects of ionization and penetration enhancers on the transdermal delivery of 5-fluorouracil through excised human stratum corneum. Int J Pharm, 298:98–107.
   PubMed Web of Science ®Google Scholar
• Aungst BJ, Rogers NJ, Shefter E. (1986). Enhancement of naloxone penetration through human skin in vitro using fatty acids, fatty alcohols, surfactants, sulfoxides and amides. Int J Pharm, 33:225–34.
   Web of Science ®Google Scholar
• Vávrová K, Lorencová L, Klimentová J, Novotný J, Holý A, Hrabálek A. (2008). Transdermal and dermal delivery of adefovir: Effects of pH and permeation enhancers. Eur J Pharm Biopharm, 69:597–604.
   PubMed Web of Science ®Google Scholar
• Levin J, Maibach HI. (2008). Human skin buffering capacity: An overview. Skin Res Technol, 14:121–6.
   PubMed Web of Science ®Google Scholar
• Hori M, Satoh S, Maibach HI, Guy RH. (1991). Enhancement of propranolol hydrochloride and diazepam skin absorption in vitro: Effect of enhancer lipophilicity. J Pharm Sci, 80:32–5.
   PubMed Web of Science ®Google Scholar
• Suhonen TM, Bouwstra JA, Urtti AJ. (1999). Chemical enhancement of percutaneous absorption in relation to stratum corneum structural alterations. J Control Release, 59:149–61.
   PubMed Web of Science ®Google Scholar
• Roberts MS, Cross SE, Pellett MA. (2002) Skin transport in dermatological and transdermal fourmulations. In: Walters KA, ed. Dermatological and transdermal formulations. New York: Marcel Dekker, 89–185.
   Google Scholar
• Plessis JD, Pugh WJ, Judefeind A, Hadgraft J. (2002). Physico-chemical determinants of dermal drug delivery: Effects of the number and substitution pattern of polar groups. Eur J Pharm Sci, 16:107–12.
   PubMed Web of Science ®Google Scholar
• Wertz PW. (1992). Epidermal lipids. Semin Dermatol, 11:106–13.
   PubMedGoogle Scholar
• Pugh WJ, Roberts MS, Hadgraft J. (1996). Epidermal permeability-penetrant structure relationships. 3. The effect of hydrogen-bonding interactions and molecular-size on diffusion across the stratum-corneum. Int J Pharm, 138:149–65.
   Web of Science ®Google Scholar
• Plessis JD, Pugh WJ, Judefeind A, Hadgraft J. (2001). The effect of hydrogen bonding on diffusion across model membranes: Consideration of the number of H-bonding groups. Eur J Pharm Sci, 13:135–41.
   PubMed Web of Science ®Google Scholar
• Izumoto T, Aioi A, Uenoyama S, Kuriyama S. (1992). Relationship between the transference of a drug from a transdermal patch and the physicochemical properties. Chem Pharm Bull, 40:456–8.
   PubMed Web of Science ®Google Scholar
• Kaplun-Frischoff Y, Touitou E. (1997). Testosterone skin permeation enhancement by menthol through the formation of a eutectic with drug and interaction with skin lipids. J Pharm Sci, 86:1349–99.
   Google Scholar
• Stott W, Williams AC, Barry BW. (1997). Transdermal delivery from eutectic systems: Enhanced permeation of a model drug, ibuprofen. J Control Release, 50:297–308.
   Web of Science ®Google Scholar
• Monene LM, Goosen C, Breytenbach JC, Hadgraft J. (2005). Percutaneous absorption of cyclizine and its alkyl analogues. Eur J Pharm Sci, 24:239–44.
   PubMed Web of Science ®Google Scholar