759
Views
77
CrossRef citations to date
0
Altmetric
Reviews

Chemical penetration enhancers: a patent review

, , , , , & show all
Pages 969-988 | Published online: 24 Jun 2009

Bibliography

  • Leonard RB, Matthias MT, Charles FB. Dermal penetration enhancer and drug delivery systems involving same. JP2007326867; 2007
  • Timothy MM, Nina WF, Katgryn KT, et al. Transdermal delivery rate control using amorphous pharmaceutical compositions. US2005175680; 2005
  • Amar L, Geena M. Transdermal pharmaceutical spray formulations comprising a vp/va copolymer and a non-aquous vehicle. US2007219171; 2007
  • Carlos S, Scott KF, Robert GJ. Non-steroidal antiinflammatory drug formulations for topical application to the skin. CA2299288; 1999
  • Schaefer H, Redelmeier TE. Structure and dynamics of the skin barrier. In: Schaefer H, Redelmeier TE, editors, Skin Barrier. Karger,Tokyo, Japan; 1996. p. 1-33
  • Asbill CS, Michniak BB. Percutaneous penetration enhancers: local versus transdermal activity. PSTT 2000;3:36-41
  • Kanikkannan N, Kandimalla K, Lamba SS, Singh M. Structure activity relationship of chemical penetration enhancers in transdermal drug delivery. Curr Med Chem 2000;7:593-608
  • Norberto RCD, Arnaud G, Celine B. Pharmaceutical compositions of nicotine and methods of use thereof. WO2008012071; 2008
  • Anant PK. A transdermal topical composition and its uses. CA2602018; 2006
  • Buyuktimkin N, Buyuktimkin S, Rytting JH. Chemical means of transdermal drug permeation enhancement. In: Ghosh TK, Pfister WR, Yum SI, editors, Transdermal and Topical Drug Delivery Systems, Interpharm Press, IL, 1997. p. 357-475
  • Barry BW. Dermatological formulations: percutaneous absorption, Marcel Dekker, New York; 1983
  • Shah VP. Skin penetration enhancers: scientific perspective. In: Hsieh DS, editor, Drug Permeation and Enhancement Marcel Dekker, New York, USA; 1994. p. 19-23
  • Smith EW, Maibach HI. Percutaneous penetration enhancers: the fundamentals. Chapter 1.1. In: Smith EW, Maibach HI, editors, Percutaneous Penetration Enhancers. CRC Press, Boca Raton; 1995. p. 1-4
  • Chattaraj SC, Walker RB. Chapter 2. In: Smith EW, Maibach HI, editors, Percutaneous Penetration Enhancers. CRC Press, Boca Raton1; 1995. p. 5-20
  • Alexander H, Pavel D, Oldrich FM, et al. Omega-amino acid derivatives, processes of their preparation and their use. US6187938; 2001
  • Goodman M, Barry BW. Lipid– protein partitioning theory (LPP) theory of skin enhancer activity: finite dose technique. Int J Pharm 1989;57:29-40
  • Chensheng L. Composition and methods for transdermal delivery of acid-labile drugs. MX9705070; 1998
  • Golden GM, McKie JE, Potts RO. Role of stratum corneum lipid fluidity in transdermal drug flux. J Pharm Sci l987;76:25-8
  • Angela AN, Samir R, Vesna A. Formulations and methods for enhancing the transdermal penetration of a drug. US2007065494; 2007
  • Chi SC, Park ES, Kim H. Effect of penetration enhancers on flurbiprofen permeation through rat skin. Int J Pharm 1995;126:267-74
  • Schroeder IZ, Franke P, Schaefer UF, Lehr CM. Delivery of ethinylestradiol from film forming polymeric solutions across human epidermis in vitro and in vivo in pigs. J Control Release 2007;118:196-203
  • Gao S, Singh J. Effect of oleic acid:ethanol and oleic acid:propylene glycol on the in vitro percutaneous absorption of 5-fluorouracil and tamoxifen and the macroscopic barrier property of porcine epidermis. Int J Pharm 1998;165:45-55
  • Cotte M, Dumas P, Besnard M, et al. Synchrotron FT-IR microscopic study of chemical enhancers in transdermal drug delivery: example of fatty acids. J Control Release 2004;97:269-81
  • Tanojo H, Boelsma E, Junginger HE, et al. In vivo human skin barrier modulation by topical application of fatty acids. Skin Pharm Appl Skin Phys 1998;11:87-97
  • Paraskevas D, Dimitrios R, Theodora G. Pharmaceutical composition for the systemic delivery of ketotifen through the skin. GR1004995; 2005
  • Chaim A, Oren C, Rami BO, et al. Pharmaceutical composition and method for transdermal drug delivery. US2005020552; 2005
  • Danyi Q, Ana R, Angela A. Norethindrone sustained release formulations and methods associated therewith. WO2005060540; 2005
  • Robert DE. Method for treating erectile dysfunction and increasing libido in men. CA2420895; 2002
  • Uday J, Charles ED, Srinivasan V. Drug delivery compositions for improved stability of steroids. MX9800545; 1998
  • Woong CJ, Deog SJ, Min PC. Transdermal composition of an antivomiting agent. WO2004054552; 2004
  • Carla GN, Matthias MT, Charles FB, Leonard RB. Topical cosmetic compositions for transdermal delivery. NZ537359; 2006
  • Srinivasan V, David F, Sonal P. Fatty acid esters of lactic acid salts as permeation enhancers. WO9818417; 1998
  • Franz-Josef B. Transdermal device for the delivery of alfuzosin. WO9630020; 1996
  • Thomas HD, Lothar D. Transdermal system per admin. of galanthamine – esp. for treatment of Alzheimer's disease and alcohol addiction. DE4301783; 1994
  • Nicholas B, Thorsteinn L. Percutaneous penetration enhancer of oleic acid and 2-ethyl-1,3-hexanediol. US4983396; 1991
  • Nicholas B, Thorsteinn L. Percutaneous penetration enhancer of oleic acid and 2-ethyl-1,3-hexanediol. US4885174; 1989
  • Lee FM, Owen PR. Transdermal flux enhancing pharmaceutical compositions containing 15-75% ethanol and penetration enhancer. NZ222346; 1990
  • Nicholas B, Thorsteinn L. Transdermal delivery system. CA1280974; 1991
  • Bruce A, Robert DC. Trandermal delivery of opioids. US4626539; 1986
  • Funke AP, Schiller R, Motzkus HW, et al. Transdermal delivery of highly lipophilic drugs: in vitro fluxes of antiestrogens, permeation enhancers, and solvents from liquid formulations. Pharm Res 2002;19:661-68
  • Sinha VR, Kaur MP. Permeation enhancers for transdermal drug delivery. Drug Dev Ind Pharm 2000;26(11):1131-40
  • Okabe H, Obata Y, Takayama K, Nagai T. Percutaneous absorption enhancing effect and skin irritation of monocyclic monoterpenes. Drug Des Deliv 1990;6:229-38
  • Williams AC, Barry BW. Terpenes and the lipid protein partitioning theory of skin penetration enhancement. Pharm Res 1991;8:17-24
  • Lim PF, Liu XY, Kang L, et al. Physicochemical effects of terpenes on organogel for transdermal drug delivery. Int J Pharm 2008;358:102-7
  • Font AF, Fernandez CB, Merino V, et al. Effect of chemical enhancers on the in vitro percutaneous absorption of sumatriptan succinate. Eur J Pharm Biopharm 2005;61:50-5
  • Amnuaikit C, Ikeuchi I, Ogawara K, et al. Skin permeation of propranolol from polymeric film containing terpene enhancers for transdermal use. Int J Pharm 2005;289:167-78
  • Ogiso T, Iwaki M, Paku T. Effect of various enhancers on transdermal penetration of indomethacin and urea, and relationship between penetration parameters and enhancement factors. J Pharm Sci 1995;84:482-88
  • Rizwan M, Aqil M, Ahad A, et al. Transdermal delivery of valsartan: I. Effect of various terpenes. Drug Dev Ind Pharm 2008;34:618-26
  • Sukhon L, Chin-Ming C, James C, Orest O. Transdermal drug delivery system. WO2008058220; 2008
  • Jain R, Aqil M, Ahad A, et al. Basil oil is a promising skin penetration enhancer for transdermal delivery of labetolol hydrochloride. Drug Dev Ind Pharm 2008;34(4):384-89
  • Norberto CDR, Arnaud G, Celine B, et al. Permeation enhancer comprising genus curcuma or germacrone for transdermal and topical administration of active agents. WO2005105059; 2005
  • Norberto CDR, Arnaud G, Celine B, et al. Permeation enhancer comprising genus Curcuma or germacrone for transdermal and topical administration of active agents. US2005244522; 2005
  • Lu MF, Hui H. Transdermal drug delivery composition. WO9008553; 1999
  • Deog SJ, Min PC, Kwon CY, et al. Transdermal drug delivery system for anti-inflammatory analgesic agent comprising diclofenac diethylammonium salt, and the manufacturing method thereof. US6723337; 2004
  • Andega S, Kanikkannan N, Singh M. Comparison of the effect of fatty alcohols on the permeation of melatonin between porcine and human skin. J Control Release 2001;77:17-25
  • Kanikkannan N, Singh M. Skin permeation enhancement effect and skin irritation of saturated fatty alcohols. Int J Pharm 2002;248:219-28
  • David KP, Juan MA. Compositions and methods for delivery of amino-functional drugs. US2007212410; 2007
  • David KP, Juan MA. Compositions and methods for delivery of amino-functional drugs. WO2007100757; 2007
  • Benjamin KK. Nitroglycerin transdermal delivery system. EP0224981; 1987
  • Santoyo S, Arellano A, Ygartua P, Martin C. Penetration enhancer effects on the in–vitro percutaneous absorption of piroxicam through rat skin. Int J Pharm 1995;117:219-24
  • Bhatt PP, Rytting JH, Topp EM. Influence of azone and lauryl alcohol on the transport of acetaminophen and ibuprofen through shed snake skin. Int J Pharm 1991;72:219-26
  • Turunen TM, Buyuktimkin S, Buyuktimkin N, et al. Enhancer delivery of 5-fluorouracil through shed snake skin by two transdermal penetration enhancers. Int J Pharm 1993;92:89-95
  • Itoh T, Wasinger L, Turunen TM, Rytting JH. Effects of transdermal penetration enhancers on the permeability of shed snake skin. Pharm Res 1992;9:1168-72
  • Barry BW, Southwell D, Woodford R. Optimization of bioavailability of topical steroids: penetration enhancers under occlusion. J Invest Dermatol 1984;82:49-52
  • Priborsky J, Takayama K, Nagai T, et al. Comparison of penetration-enhancing ability of laurocapram, N-methyl-2-pyrrolidone and dodecyl-L-pyroglutamate. Pharm Weekbl Sci 1988;10(5):189-92
  • Akhter SA, Barry BW. Absorption through human skin of ibuprofen and flurbuprofen: effect of dose variation, deposited drug films, occlusion and the penetration enhancer N-methyl-2-pyrrolidone. J Pharm Pharmacol 1985;37:27-37
  • Kim DD, Chien YW. Transdermal delivery of zalcitabine (DDC): in vitro skin permeation study. AIDS 1995;9:1331-36
  • Kim DD, Chien YW. Transdermal delivery of dideoxynucleosidetype anti-HIV drugs. 2. The effect of vehicle and enhancer on skin permeation. J Pharm Sci 1996;85:214-19
  • Sharad GK, Edward RM, Dale SG. Transdermal nitroglycerin patch with penetration enhancers. US5262165; 1993
  • Sharad GK, Edward RM, Dale SG. Transdermal nitroglycerin patch with penetration enhancers. EP0417496; 1991
  • Babu RJ, Dhanasekaran M, Vaithiyalingam SR, et al. Cardiovascular effects of transdermally delivered bupranolol in rabbits: effect of chemical penetration enhancers. Life Sci 2008;82:273-8
  • Williams AC, Barry BW. Penetration enhancers. Adv Drug Deliv Rev 2004;56:603-18
  • Barry BW. Mode of action of penetration enhancers in human skin. J Control Release 1987;6:85-97
  • Anigbogu ANC, Williams AC, Barry BW, Edwards HGM. Fourier transform Raman spectroscopy of interactions between the penetration enhancer dimethylsulphoxide and human stratum corneum. Int J Pharm 1995;125:265-82
  • Smith EW, Maibach HI. In: Smith EW, Maibach HI, editors, Percutaneous Penetration Enhancers, CRC Press, New York; 1995. p. 1-4
  • Embery G, Dugrad PH. The isolation of DMSO soluble components from human epidermis preparations: a possible mechanism of action of dimethylsulfoxidc in affecting percutaneous migration phenomena. J Invest Dermatol 1971;57:308-31
  • Carpentieri-Rodrigues LN, Zanluchi JM, Hinke I. Percutaneous absorption enhancers: mechanisms and potential. Brazil Arch Bio Tech 2007;50:949-61
  • Clancy MJ, Corish J, Corrigan OI. A comparison of (the effects of electrical current and penetration enhancers on the properties of human skin using spectroscopic (FTIR) and calorimetric (DSC) methods. Int J Pharm 1994;105:47-56
  • Xu GQ, Xi NZ, Chen GS, et al. Effect of enhancers on cutaneous permeation of piroxicam in vitro. Chung Kuo Yao Li Hsueh Pao 1991;12(3):235-38
  • David RM, George DR. Topical preparation and method for transdermal delivery and localization of therapeutic agents. WO2005120407; 2005
  • Doron F, Joseph S, Haim A. Topical and transdermal delivery system utilizing submicron oil spheres. WO9318752; 1993
  • Doron F, Joseph S, Haim A. Topical and transdermal delivery system utilizing submicron oil spheres. US6113921; 2000
  • Cornwell PA, Barry BW. The effects of a series of homologous terpene alcohols on the lipid structure of human stratum corneum as assessed by differential scanning calorimetry. In: Scott RC, Guy RH, Hadgraft J, Bodd HEC, editors, Prediction of Percutaneous Absorption. Vol. 2. IBC Technical Services. London; 1992. p. 394-400
  • Parikh DK, Ghosh TK. Feasibility of transdermal delivery of fluoxetine. AAPS PharmSciTech 2005;6(2):E114-49
  • Tenjarla SN, Holbrook JH, Pvranajoti P, et al. Evaluating the irritation potential of skin penetration enhancers in the hairless guinea pig. Cutan Ocul Toxicol 1995;14:299-307
  • Goodman M, Barry BW. Action of penetration enhancers on human skin as assessed by the permeation of model drugs 5-fluorouracil and estradiol. J Invest Dermatol 1988;91:323-27
  • Owen PR, Lee FM. Transdermal flux enhancing compositions. EP0331382; 1989
  • Michael FL, Russell PO. Transdermal flux enhancing compositions to treat hypertension, diabetes and angina pectoris. US5391548; 1995
  • Ruland A, Kreuter J. Influence of various penetration enhancers on the in vitro permeation of amino acids across hairless mouse skin. Int J Pharm 1992;85:7-17
  • Gevork M, James PV. Penetration enhancers for transdermal delivery of systemic agents. US4886783; 1989
  • Igor G, Matthias MT, Frances WN, et al. Method and system for rapid transdermal administration. MXPA06006041; 2007
  • Vithal RJ. Penetration enhancers for transdermal drug delivery of systemic agents. US4562075; 1985
  • Vithal RJ. Improved penetration enhancers for transdermal drug delivery of systemic agents. EP0095169; 1983
  • Vithal RJ. Penetration enhancers for transdermal drug delivery of systemic agents. US4405616; 1983
  • Gevork M, James VP, Eric LN. Penetration enhancers for transdermal delivery of systemic agents. US5270346; 1993
  • Stoughton RB. Azone (l-dodecylazacycloheptan-2-one) enhances percutaneous penetration. In: Farber EM, editor, Psoriasis, Grune and Stratton. Orlando, FL; 1982. p. 346-98
  • Turkoglu M, Sakr A. Evaulation of irritation potential of surfactant mixtures. Int J Cos Sci 2001;21:371-82
  • Ribaud C, Garson J, Doucet J, Leveque J. Organization of stratum corneum lipids in relation to permeability: Influence of sodium lauryl sulphate and preheating. Pharm Res IL 1994;11(10):1414-18
  • Samir M, Pankaj KS, Amit JK. Penetration enhancer combinations for transdermal delivery. US2007269379; 2007
  • Kimu BK. Article for percutaneous medication of estradiol. JP2003607; 1990
  • Kim CK, Kim JJ, Chi SC, Shim CK. Effect of fatty acids and urea on the penetration of ketoprofen through rat skin. Int J Pharm 1993;99:109-18
  • Chaim A, Oren C, Rami BO, et al. Pharmaceutical composition and method for transdermal drug delivery. US2005042268; 2005
  • Naohisa K, Ken-Ichi NG, Junji K, et al. Pharmaceutical composition for topical delivery of meloxicam comprising an amine or amine as penetration enhancer. WO2004026313; 2004
  • George EKF. Topical application of muscarinic analgesic drugs such as neostigmine. US6011022; 2000
  • George EKF. Topical application of muscarinic analgesic drugs such as neostigmine. WO0135927; 2001
  • George EK. Topical application of muscarinic analgesic drugs such as neostigmine. TW265027B; 2006
  • George EKF. Topical application of opioid analgesic drugs such as morphine. US6143278; 2000
  • Okumura M, Nakamori Y, Sugibayashi K, Morimoto Y. Enhanced skin permeation of papaverine by a medium chain glyceride. Drug Des Deliv 1991;7:147-57
  • Ben-Shabat S, Baruch N, Sintov AC. Conjugates of unsaturated fatty acids with propylene glycol as potentially less-irritant skin penetration enhancers. Drug Dev Ind Pharm 2007;33:1169-75
  • Ju KJ, Hyun BW, Chul LY, Gyu CY. Medicinal patches for percutaneous administration. WO9619976; 1996
  • Danyi Q, Ninad D, Srinivasan V, Charles ED. Triacetin as a transdermal penetration enhancer. MX9707868; 1997
  • Dong-son M, Kee-an U, Yong-soo K, et al. Transdermal delivery matrix for piroxicam. US5916587; 1999
  • Mura P, Faucci MT, Bramanti G, Corti P. Evaluation of transcutol as a clonazepam transdermal permeation enhancer from hydrophilic gel formulations. Eur J Pharm Sci 2000;9(4):365-72
  • Gene J, Norberto CD, Arnaud G. Pharmaceutical compositions of ropinirole and methods of use thereof. WO2008005240; 2008
  • Montague SC, Biljana T, Louis SD. Transdermal drug delivery systems. US2005287195; 2005
  • Chaim A, Oren C, Rami BO, et al. Pharmaceutical composition and method for transdermal drug delivery. US2005025833; 2005
  • David F, Charles ED, Srinivasan V, Lawrence NR. Transdermal drug delivery systems containing quaternary ammonium salts and methods of using the same. US2003091620; 2003
  • James YL. Topical compositions for prostaglandin E1. MXPA01011560; 2002
  • Nadir B, James YL, Servet B. Topical compositions for prostaglandin E1 delivery. CA2442479; 2000
  • Gevork M, James PV. Penetration enhancers for transdermal delivery of systemic agents. US5118676; 1992
  • James PV. Penetration enhances for transdermal delivery of systemic agents. US5118692; 1992
  • Nina W, Tony DP, Monique R, et al. Method and composition for transdermal drug delivery. CA2610708; 2006
  • Chin KH, Jeong YH. Hydrogel composition for transdermal drug delivery. NZ522532; 2005
  • Seung BJ, Ung CJ, Han LH. Pharmaceutical composition for treatment of erectile dysfunction and device for transdermal administration of formulation. KR100287626B; 2001
  • Chien YW, Xu H, Chiang CC, Hung YC. Transdermal controlled administration of indomethacin: I. Enhancement of skin permeability. Pharm Res 1988;5:103-6
  • Porzio S, Caselli G, Pellegrini L, et al. Efficacy of a new topical gel-spray formulation of ketoprofen lysine salt in the rat: percutaneous permeation in vitro and in vivo and pharmacological activity. Pharmacol Res 1998;37:41-7
  • Friend D, Catz P, Heller J, et al. Transdermal delivery of levonorgestrel I. Alkanols as permeation enhancers. J Control Release 1988;7:243-50
  • Pershing LK, Lambert LD, Knutson K. Mechanism of ethanol-enhanced estradiol permeation across human skin in vivo. Pharm Res 1990;7:170-75
  • Friend D, Catz P, Hellcr J, et al. Simple alkyl esters as skin permeation enhancers. J Control Release l989;9:33-41
  • Sato K, Sugibayashi K, Morimoto Y. Effect and mode of action of aliphatic esters on in vitro skin permeation of nicorandil. Int J Pharm 1988;43:31-40
  • Hori M, Satoh S, Maibach HI, Guy RH. Enhancement of propranolol hydrochloride and diazepam skin absorption in vitro: effect of enhancer lipophilicity. J Pharm Sci 1991;80:32-35
  • Melendres JL, Nangia A, Sedik A, et al. Nonane enhances propranolol hydrochloride penetration in human skin. Int J Pharm 1993;92:243-48
  • Rizwan M, Azeem A, Aqil A, et al. Enhanced transdermal drug delivery techniques: an extensive review of patents. Rec Patents Drug Deliv Form 2009;3: (Article in press)
  • Aqil M, Ahad A, Sultana Y, Ali A. Status of terpenes as skin penetration enhancers. Drug Discov Today 2007;12:1061-67

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.