A review on terpenes as skin penetration enhancers in transdermal drug delivery

Journal of Essential Oil Research

Volumn 21, Issue 5, 2009, Pages 423-428

  Lim, Perry Fung Chye ^a   Liu, Xiang Yang ^a   Chan, Sui Yung ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Penetration enhancers; Skin penetration; Terpenes; Transdermal drug delivery

Indexed keywords

ANALYTICAL TECHNIQUES; CHEMICAL PENETRATION ENHANCER; CONVENTIONAL APPROACH; DELIVERY MODES; DRUG PERMEATION; HYDROPHILIC AND HYDROPHOBIC; LIPID EXTRACTION; MOLECULAR SIZE; MONOTERPENES; NON-INVASIVE; PENETRATION ENHANCERS; SKIN PENETRATION; SKIN STRUCTURE; TERPENES; THERAPEUTIC AGENTS; TRANSDERMAL DRUG DELIVERY;

CONTROLLED DRUG DELIVERY; ESSENTIAL OILS; LIPIDS; NEEDLES; OLEFINS; PHASE SEPARATION;

SKIN;

EID: 70349682587     PISSN: 10412905     EISSN: None     Source Type: Journal    
DOI: 10.1080/10412905.2009.9700208     Document Type: Article

References (56)

1. P. Gupta and S. Garg, Recent advances in semisolid dosage forms for dermatological application. Pharm. Technol., 26, 144-161 (2002).
2. T.D. Downing, Lipid and protein structures in the permeability barrier of mammalian epidermis. J. Lipid Res., 33, 301-313 (1992).
3. G.P Moss, J.C. Dearden, H. Patel and M.T.D. Cronin, Quantitative structure-permeability relationships (QSPRs) for percutaneous absorption. Toxicol. In Vitro., 16, 299-317 (2002).
4. J. Hadgraft and M.E. Lane, Skin permeation: the years of enlightenment. Int. J. Pharm., 305, 2-12 (2005).
5. T.M. Suhonen, J.A. Bouwstra and A. Urtti, Chemical enhancement of percutaneous absorption in relation to stratum corneum structural alterations. J. Control. Rel., 59, 149-161 (1999).
6. J.A. Bouwstra, F.E.R. Dubblelaar, G.S. Gooris and M. Ponec, The lipid organization in the skin barrier. Acta Derm Venereol., Supp 208, 23-30 (2000).
7. M.W.D. Jager, G.S. Gooris, I.P. Dolbnya, M. Ponec and J.A. Bouwstra, Modeling the stratum corneum lipid organisation with synthetic lipid mixtures: the importance of synthetic ceramide composition. Biochim. Biophys. Acta. 1684, 132-140 (2004).
8. P.W. Wertz, Lipids and barrier function of the skin. Acta Derm Venereol., Supp 208, 7-11 (2000).
9. B.W. Barry, Breaching the skin’s barrier to drugs. Nat. Biotechnol., 22, 165-167 (2004).
10. M.K. Nemanic and P.M. Elias, In situ precipitation: a novel technique for visualization of permeability pathways in mammalian stratum corneum. J. Histochem. Cytochem., 28, 573-578 (1980).
11. F. Yamashita and M. Hashida, Mechanistic and empirical modeling of skin permeation of drugs. Adv. Drug Deliv. Rev., 55, 1185-1199 (2003).
12. R.B. Walker and E.W. Smith, The role of percutaneous penetration enhancers. Adv. Drug Deliv. Rev., 18, 295-301 (1996).
13. I. Lavon and J. Kost, Ultrasound and transdermal drug delivery. Drug Discov. Today, 9, 670-676 (2004).
14. G. Merino, Y.N. Kalia and R.H. Guy, Ultrasound-enhanced transdermal transport. J. Pharm. Sci., 92, 1125-1137 (2003).
15. P.G. Green, Lontophoretic delivery of peptide drugs. J. Control. Rel., 41, 33-8 (1996).
16. A. Naik, Y.N. Kalia and R.H. Guy, Transdermal drug delivery: overcoming the skin’s barrier function. Pharm. Sci. Technol. Today, 3, 318-326 (2000).
17. M. Hashida and F. Yamashita, Terpenes as penetration enhancers. In: Percutaneous Penetration Enhancers. Edits., E.W. Smith and H.I. Maibach, pp. 309-321, CRC Press, Florida (1995).
18. B.W. Barry, Lipid-protein-partitioning theory of skin penetration enhancement. J. Control. Rel., 15, 237-248 (1991).
19. A.C. Williams and B.W. Barry, Penetration enhancers. Adv. Drug Deliv. Rev., 56, 603-618 (2004).
20. D.A. Godwin and B.B. Michniak, Influence of drug iipophilicity on terpenes as transdermal penetration enhancers. Drug Dev. Ind. Pharm., 25, 905-915 (1999).
21. P.F.C. Lim, X.Y. Liu, L. Kang, P.C.L. Ho, Y.W. Chan and S.Y. Chan, Limonene GP1/PG organogel as a vehicle in the transdermal delivery of haloperidol. Int. J. Pharm., 311, 157-164 (2006).
22. M. Almirall, J. Montana, E. Escribano, R. Obach and J.D. Berrozpe, Effect of d-limonene, a-pinene and cineole on in vitro transdermal human skin penetration of chloropromazine and haloperidol. Drug Res., 46, 676-680 (1996).
23. P.A. Cornwell and B.W. Barry, Sesquiterpene components of volatile oils as skin penetration enhancers for the hydrophilic permeant 5-fluorouracil. J. Pharm. Pharmacol., 46, 261-269 (1994).
24. M.A. Yamane, A.C. Williams and B.W. Barry, Effects of terpenes and oleic acid as skin penetration enhancers towards 5-fluorouracil as assessed with time; permeation, partitioning and differential scanning calorimetry. Int. J. Pharm., 116, 237-251 (1995).
25. Y.S.R. Krishnaiah, P. Bhaskar and V. Satyanarayana, Formulation and evaluation of limonene-based membrane-moderated transdermal therapeutic system of nimodipine. Drug Deliv., 11, 1-9 (2004).
26. J.R. Kunta, V.R. Goskonda, H.O. Brotherton, M.A. Khan and I.K. Reddy, Effect of menthol and related terpenes on the percutaneous absorption of propranolol across excised hairless mouse skin. J. Pharm. Sci., 86, 1369-1373 (1997).
27. T.T. Kararli, C.F. Kirchhoff and S.C. Penzotti, Enhancement of transdermal transport of azidothymidine (AZT) with novel terpene and terpene-like enhancers: in vivo-in vitro correlations. J. Control. Rel., 34, 43-51 (1995).
28. Y.S.R. Krishnaiah, V. Satyanarayana and P. Bhaskar, Influence of menthol and pressure-sensitive adhesives on the in vivo performance of membranemoderated transdermal therapeutic system of nicardipine hydrochloride in human volunteers. Eur. J. Pharm. Biopharm., 55, 329-337 (2003).
29. A. Nokhodchi, K. Sharabiani, M.R. Rashidi and T. Ghafourian, The effect of terpene concentrations on skin penetration of diclofenac sodium. Int. J. Pharm., 335, 97-105 (2007).
30. R.J. Babu and J.K. Pandit, Effect of penetration enhancers on the transdermal delivery of bupranolol through rat skin. Drug Deliv., 12, 165-169 (2005).
31. A.F. Font, C.B. Fernandez, V. Merino, V. Rodilla and A.L. Castellano, Effect of chemical enhancers on the in vitro percutaneous absorption of sumatriptan succinate. Eur. J. Pharm. Biopharm., 61, 50-55 (2005).
32. L. Kang, X.Y. Liu, P.D. Sawant, P.C. Ho, Y.W. Chan and S.Y. Chan, SMGA gels for the skin permeation of haloperidol. J. Control. Rel., 106, 88-98 (2005).
33. H.K. Vaddi, P.C. Ho, Y.W. Chan and S.Y. Chan, Terpenes in ethanol: haloperidol permeation and partition through human skin and stratum corneum changes. J. Control. Rel., 81, 121-133 (2002).
34. K. Zhao and J. Singh, Mechanism(s) of in vitro percutaneous absorption enhancement of tamoxifen by enhancers. J. Pharm. Sci., 89, 771-780 (2000).
35. P.A. Cornwell and B.W. Barry, The routes of penetration of ions and 5-fluorouracil across human skin and the mechanisms of action of terpene skin penetration enhancers. Int. J. Pharm., 94, 189-194 (1993).
36. C. Amnuaikit, I. Ikeuchi, K. Ogawara, K. Higaki and T. Kimura, Skin permeation of propranolol from polymeric film containing terpene enhancers for transdermal use. Int. J. Pharm., 289, 167-178 (2005).
37. S.T.K. Narishetty and R. Panchagnula, Transdermal delivery ofzidovudine: effect of terpenes and their mechanism of action. J. Control. Rel., 95, 367-379 (2004).
38. H. Ueda, R. Isshiki, M. Ogihara, K. Sugibayashi and Y. Morimoto, Combined effect of ultrasound and chemical enhancers on the skin permeation of aminopyrine. Int. J. Pharm., 143, 37-45 (1996).
39. S.K. Rastogi and J. Singh, Effect of chemical penetration enhancers and iontophoresis on the in vitro percutaneous absorption enhancement of insulin through porcine epidermis. Pharm. Dev. Tech., 1, 97-104 (2005).
40. S. Engstrom, K. Ekelund, J. Engblom, L. Eriksson, E. Sparr and H. Wennerstrom, The skin barrier from a lipid perspective. Acta Derm Venereol., Supp 208, 31-35 (2000).
41. M.Y. Wang, Y.Y. Yang and P.W.S. Heng, Skin permeation of physostigmine from fatty acids-based formulations: evaluating the choice of solvent. Int. J. Pharm., 290, 25-36 (2005).
42. M.Y. Wang, Y.Y. Yang and P.W.S. Heng, Role of solvent in interactions between fatty acids-based formulations and lipids in porcine stratum corneum. J. Control. Rel., 94, 207-216 (2004).
43. K. Knutson, R.O. Potts, D.B. Guzek, G.M. Golden, J.E. McKie, W.J. Lambert, W.I. Higuchi, Macro- and molecular physical-chemical considerations in understanding drug transport in the stratum corneum. J. Control. Rel., 2, 67-87 (1985).
44. A.K. Jain, N.S. Thomas and R. Panchagnula, Transdermal drug delivery of imipramine hydrochloride. I. Effect of terpenes. J. Control. Rel., 79, 93-101 (2002).
45. B. Ongpipattanakul, R.R. Burnette, R.O. Potts and M.L. Francoeur, Evidence that oleic acid exists in a separate phase with stratum corneum lipids. Pharm. Res., 8, 350-354 (1991).
46. H.R. Moghimi, A.C. Williams and B.W. Barry, A lamellar matrix model for stratum corneum intercellular lipids. V. Effects of terpene penetration enhancers on the structure and thermal behaviour of the matrix. Int. J. Pharm., 146, 41-54 (1997).
47. R. Panchagnula, H. Desu, A. Jain and S. Khandavilli, Feasibility studies of dermal delivery of paclitaxel with binary combinations of ethanol and isopropyl mysristate: role of solubility, partitioning and lipid bilayer perturbation. Il Farmaco., 60, 894-899 (2005).
48. H.K. Vaddi, P.C. Ho and S.Y. Chan, Terpenes in propylene glycol as skin-penetration enhancers: permeation and partition of haloperidol, fourier transform infrared spectroscopy and differential scanning calorimetry. J. Pharm. Sci., 91, 1639-1651 (2002).
49. Y.S.R. Krishnaiah, V. Satyanarayana and P. Bhaskar, Effect of limonene on the in vitro permeation of nicardipine hydrochloride across the excised rat abdominal skin. Pharmazie, 57, 842-847 (2002).
50. H.K. Vaddi, P.C. Ho, Y.W. Chan and S.Y. Chan, Oxide terpenes as human skin penetration enhancers of haloperidol from ethanol and propylene glycol and their modes of action on stratum corneum. Biol. Pharm. Bull., 26, 220-228 (2003).
51. 8-THC development. J. Pharm. Sci., 93, 1154-1164 (2004).
52. R. Panchagnula, R. Bokalial, P. Sharma and S. Khandavilli, Transdermal delivery of naloxone: skin permeation, pharmacokinetic, irritancy and stability studies. Int. J. Pharm., 293, 213-223 (2005).
53. Y.S.R. Krishnaiah, S.M. Al-Saidan, D.V. Chandrasekhar and V. Satyanarayana, Bioavailability of nerodilol-based transdermal therapeutic system of nicorandilin human volunteers. J. Control. Rel., 106, 111-122 (2005).
54. Handbook of Physical Properties of Organic Chemicals. Edits., P.H. Howard and W.M. Meylan, CRC Press, Florida (1997).
55. DrugBank. http://redpoll.pharmacy.ualberta.ca/drugbank/index.html. Accessed on Dec 13, 2007.
56. Syracuse Research Corporation. http://www.syrres.com/esc/est_ kowdemo.htm. Accessed on Dec 13, 2007.