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Volumn 23, Issue 1, 2006, Pages 67-87

Design of fatty acid conjugates for dermal delivery and topical therapeutics

Author keywords

Penetration enhancer; Polyunsaturated fatty acids; Prodrugs; Skin permeability; Topical drugs; Transdermal drug delivery

Indexed keywords

ACICLOVIR; ADIPIC ACID; ALKANONE; CARBOXYLIC ACID; DECANOIC ACID; DICARBOXYLIC ACID; DICLOFENAC; DOPAMINE; FATTY ACID; INDOMETACIN; ISOPRENALINE; KETOPROFEN; LAURIC ACID; LEVODOPA; LIDOCAINE; LINOLEIC ACID; MYRISTIC ACID ISOPROPYL ESTER; NALTREXONE; NAPROXEN; NONSTEROID ANTIINFLAMMATORY AGENT; OCTANOIC ACID; OLEIC ACID; POLYUNSATURATED FATTY ACID; PRODRUG; PROPYLENE GLYCOL; SATURATED FATTY ACID; SEBACIC ACID; SUCCINIC ACID; UNINDEXED DRUG; UNSATURATED FATTY ACID;

EID: 33745056744     PISSN: 07434863     EISSN: None     Source Type: Journal    
DOI: 10.1615/CritRevTherDrugCarrierSyst.v23.i1.20     Document Type: Review
Times cited : (3)

References (79)
  • 1
    • 0344299548 scopus 로고
    • Penetration of low-molecular-weight alcohols into skin. I. Effect of concentration of alcohol and type of vehicle
    • Blank, IH. penetration of low-molecular-weight alcohols into skin. I. Effect of concentration of alcohol and type of vehicle. J Invest Dermatol. 1964;43:415-20.
    • (1964) J Invest Dermatol , vol.43 , pp. 415-420
    • Blank, I.H.1
  • 2
    • 1242271295 scopus 로고    scopus 로고
    • New microemulsion vehicle facilitates percutaneous penetration in vitro and cutaneous drug bioavailability in vivo
    • Sintov, AC, Shapiro, L. New microemulsion vehicle facilitates percutaneous penetration in vitro and cutaneous drug bioavailability in vivo. J Control Release. 2004;95:173-83.
    • (2004) J Control Release , vol.95 , pp. 173-183
    • Sintov, A.C.1    Shapiro, L.2
  • 3
    • 0034954840 scopus 로고    scopus 로고
    • Influence of a microemulsion vehicle on cutaneous bioequivalence of a lipophilic model drug assessed by microdialysis and pharmacodynamics
    • Kreilgaard, M, Kemme, MJB, Burggraaf, J, Schoemaker, RC, Cohen, AF. Influence of a microemulsion vehicle on cutaneous bioequivalence of a lipophilic model drug assessed by microdialysis and pharmacodynamics. Pharm Res. 2001;18:593-99.
    • (2001) Pharm Res , vol.18 , pp. 593-599
    • Kreilgaard, M.1    Kemme, M.J.B.2    Burggraaf, J.3    Schoemaker, R.C.4    Cohen, A.F.5
  • 4
    • 0042338753 scopus 로고    scopus 로고
    • Percutaneous lidocaine administration via a new iontophoresis system in children: Tolerability and absence of systemic bioavailability
    • Kearns, GL, Heacook, J, Daly, SJ, Singh, H, Alander, SW, Qu, S. Percutaneous lidocaine administration via a new iontophoresis system in children: tolerability and absence of systemic bioavailability. Pediatrics. 2003;112:578-82.
    • (2003) Pediatrics , vol.112 , pp. 578-582
    • Kearns, G.L.1    Heacook, J.2    Daly, S.J.3    Singh, H.4    Alander, S.W.5    Qu, S.6
  • 5
    • 0000888229 scopus 로고
    • A new deficiency disease produced by the rigid exclusion of fat from the diet
    • Burr, GO, Burr, MM. A new deficiency disease produced by the rigid exclusion of fat from the diet. J Biol Chem. 1929;82:345-67.
    • (1929) J Biol Chem , vol.82 , pp. 345-367
    • Burr, G.O.1    Burr, M.M.2
  • 6
    • 0001553916 scopus 로고
    • On the nature and role of the fatty acids essential in nutrition
    • Burr, GO, Burr ,MM. On the nature and role of the fatty acids essential in nutrition. J Biol Chem. 1930;86:587-621.
    • (1930) J Biol Chem , vol.86 , pp. 587-621
    • Burr, G.O.1    Burr, M.M.2
  • 7
    • 70449246507 scopus 로고
    • Essential fatty acids in infants nutrition III. Clinical manifestations of linoleic acid deficiency
    • Hansen, AE, Haggard, ME, Boelesche, AN, Adam, D, Wiese, HF. Essential fatty acids in infants nutrition III. Clinical manifestations of linoleic acid deficiency. J Nutr. 1958;66:565-76.
    • (1958) J Nutr , vol.66 , pp. 565-576
    • Hansen, A.E.1    Haggard, M.E.2    Boelesche, A.N.3    Adam, D.4    Wiese, H.F.5
  • 8
    • 0018188561 scopus 로고
    • Linoleic acid effects on epidermal DNA synthesis and cutaneous prostaglandin levels in essential fatty acid deficiency
    • Lowe, NJ, DeQuoy, PR. Linoleic acid effects on epidermal DNA synthesis and cutaneous prostaglandin levels in essential fatty acid deficiency. J Invest Dermatol. 1978;70:200-03.
    • (1978) J Invest Dermatol , vol.70 , pp. 200-203
    • Lowe, N.J.1    DeQuoy, P.R.2
  • 9
    • 0024362187 scopus 로고
    • Essential fatty acids in clinical dermatology
    • Horrobin, DF. Essential fatty acids in clinical dermatology. J Am Acad Dermatol. 1989;20:1045-53.
    • (1989) J Am Acad Dermatol , vol.20 , pp. 1045-1053
    • Horrobin, D.F.1
  • 10
    • 0026315157 scopus 로고
    • Essential fatty acids and the skin
    • Wright, S. Essential fatty acids and the skin. Br J Dermatol. 1991;125:503-15.
    • (1991) Br J Dermatol , vol.125 , pp. 503-515
    • Wright, S.1
  • 13
  • 14
    • 0642276230 scopus 로고    scopus 로고
    • Molecular models of the intercellular lipid lamellae from epidermal stratum corneum
    • Hill, JR, Wertz, PW. Molecular models of the intercellular lipid lamellae from epidermal stratum corneum. Biochim Biophys Acta. 2003;1616:121-26.
    • (2003) Biochim Biophys Acta , vol.1616 , pp. 121-126
    • Hill, J.R.1    Wertz, P.W.2
  • 15
    • 0023784154 scopus 로고
    • Oxidative metabolism of dihomo-γ-linolenic acid by guinea pig epidermis: Evidence of generation of anti-inflammatory products
    • Miller, CC, McCreedy, CA, Jones, AD, Ziboh, VA. Oxidative metabolism of dihomo-γ-linolenic acid by guinea pig epidermis: evidence of generation of anti-inflammatory products. Prostaglandins. 1988;35:917-39.
    • (1988) Prostaglandins , vol.35 , pp. 917-939
    • Miller, C.C.1    McCreedy, C.A.2    Jones, A.D.3    Ziboh, V.A.4
  • 16
    • 0037666141 scopus 로고    scopus 로고
    • Biological significance of essential fatty acids/prostanoids/ lipoxygenase-derived monohydroxy fatty acids in the skin
    • Ziboh, VA, Cho, Y, Mani, I, Xi, S. Biological significance of essential fatty acids/prostanoids/lipoxygenase-derived monohydroxy fatty acids in the skin. Arch Pharm Res. 2002;25:747-58.
    • (2002) Arch Pharm Res , vol.25 , pp. 747-758
    • Ziboh, V.A.1    Cho, Y.2    Mani, I.3    Xi, S.4
  • 17
    • 0036790051 scopus 로고    scopus 로고
    • γ-Linolenic acid in borage oil reverses epidermal hyperproliferation in guinea pigs
    • Chung, S, Kong, S, Seong, K, Cho, Y. γ-Linolenic acid in borage oil reverses epidermal hyperproliferation in guinea pigs. J Nutr. 2002;132:3090-97.
    • (2002) J Nutr , vol.132 , pp. 3090-3097
    • Chung, S.1    Kong, S.2    Seong, K.3    Cho, Y.4
  • 18
    • 0023001444 scopus 로고
    • Enhancement of naloxone penetration through human skin in vitro using fatty acids, fatty alcohols, surfactants, sulfoxides and amides
    • Aungst, BJ, Rogers, NJ, Shefter, E. Enhancement of naloxone penetration through human skin in vitro using fatty acids, fatty alcohols, surfactants, sulfoxides and amides. Int J Pharmaceut. 1986;33:225-34.
    • (1986) Int J Pharmaceut , vol.33 , pp. 225-234
    • Aungst, B.J.1    Rogers, N.J.2    Shefter, E.3
  • 19
    • 0000804856 scopus 로고
    • Penetration enhancers and their use in transdermal therapeutic systems
    • Hadgraft, J, Guy, RH, editors. New York: Marcel Dekker
    • Walters, KA. Penetration enhancers and their use in transdermal therapeutic systems. In: Hadgraft, J, Guy, RH, editors. Transdermal drug delivery, developmental issues and research initiatives. New York: Marcel Dekker; 1989. p 197-246.
    • (1989) Transdermal Drug Delivery, Developmental Issues and Research Initiatives , pp. 197-246
    • Walters, K.A.1
  • 21
    • 0001936460 scopus 로고    scopus 로고
    • Chemical means of transdermal drug permeation enhancement
    • Ghosh, TK, Pfister, WR, Yum SI, editors. Buffalo Grove, IL: Interpharm
    • 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. Buffalo Grove, IL: Interpharm; 1997. p. 357-475.
    • (1997) Transdermal and Topical Drug Delivery Systems , pp. 357-475
    • Buyuktimkin, N.1    Buyuktimkin, S.2    Rytting, J.H.3
  • 22
    • 0032883241 scopus 로고    scopus 로고
    • Transdermal penetration enhancers: Application, limitation, and potential
    • Finnin, BC, Morgan, TM. Transdermal penetration enhancers: application, limitation, and potential. J Pharm Sci. 1999;88:955-58.
    • (1999) J Pharm Sci , vol.88 , pp. 955-958
    • Finnin, B.C.1    Morgan, T.M.2
  • 23
    • 33745042088 scopus 로고    scopus 로고
    • Chemical penetration enhancement: Possibilities and problems
    • Roberts, MS, Walters, KA, editors. New York: Marcel Dekker
    • Williams, AC, Barry, BW. Chemical penetration enhancement: possibilities and problems. In: Roberts, MS, Walters, KA, editors. Dermal absorption and toxicity assessment. New York: Marcel Dekker; 1998.
    • (1998) Dermal Absorption and Toxicity Assessment
    • Williams, A.C.1    Barry, B.W.2
  • 24
    • 0024639484 scopus 로고
    • Structure/effect studies of fatty acid isomers as skin penetration enhancers and skin irritants
    • Aungst, BJ. Structure/effect studies of fatty acid isomers as skin penetration enhancers and skin irritants. Pharm Res. 1989;6:244-47.
    • (1989) Pharm Res , vol.6 , pp. 244-247
    • Aungst, B.J.1
  • 25
    • 0025118816 scopus 로고
    • Contributions of drug solubilization, partitioning, barrier disruption, and solvent permeation to the enhancement of skin permeation of various compounds with fatty acids and amines
    • Aungst, BJ, Blake, JA, Hussain, MA. Contributions of drug solubilization, partitioning, barrier disruption, and solvent permeation to the enhancement of skin permeation of various compounds with fatty acids and amines. Pharm Res. 1990;7:712-18.
    • (1990) Pharm Res , vol.7 , pp. 712-718
    • Aungst, B.J.1    Blake, J.A.2    Hussain, M.A.3
  • 26
    • 0033840314 scopus 로고    scopus 로고
    • Effect of skin pretreatment with fatty acids on percutaneous absorption and skin retention of piroxicam after its topical application
    • Santoyo, S, Ygartua, P. Effect of skin pretreatment with fatty acids on percutaneous absorption and skin retention of piroxicam after its topical application. Euro J Pharm Biopharm. 2000;50:245-50.
    • (2000) Euro J Pharm Biopharm , vol.50 , pp. 245-250
    • Santoyo, S.1    Ygartua, P.2
  • 28
    • 0032773028 scopus 로고    scopus 로고
    • Effect of fatty acids on the permeation of melatonin across rat and pig skin in-vitro and on the transepidermal water loss in rats in-vivo
    • Kandimalla, K, Kanikkannan, N, Andega, S, Singh, M. Effect of fatty acids on the permeation of melatonin across rat and pig skin in-vitro and on the transepidermal water loss in rats in-vivo. J Pharm Pharmacol. 1999;51:783-90.
    • (1999) J Pharm Pharmacol , vol.51 , pp. 783-790
    • Kandimalla, K.1    Kanikkannan, N.2    Andega, S.3    Singh, M.4
  • 29
    • 0025905320 scopus 로고
    • Evidence that oleic acid exists in a separate phase within stratum corneum lipids
    • Ongpipattanakul, B, Burnette, RR, Potts, RO, Fracoeur, ML. Evidence that oleic acid exists in a separate phase within stratum corneum lipids. Pharm Res. 1991;8:350-54.
    • (1991) Pharm Res , vol.8 , pp. 350-354
    • Ongpipattanakul, B.1    Burnette, R.R.2    Potts, R.O.3    Fracoeur, M.L.4
  • 30
    • 0029585859 scopus 로고
    • Mechanism of oleic acid-induced skin penetration enhancement in vivo in humans
    • Naik, A, Pechtold, LARM, Potts, RO, Guy, RH. Mechanism of oleic acid-induced skin penetration enhancement in vivo in humans. J Control Rel. 1995;37:299-306.
    • (1995) J Control Rel , vol.37 , pp. 299-306
    • Naik, A.1    Pechtold, L.A.R.M.2    Potts, R.O.3    Guy, R.H.4
  • 32
    • 0031805551 scopus 로고    scopus 로고
    • Fatty acid extract from cod-liver oil: Activity against herpes simplex virus and enhancement of transdermal delivery of acyclovir in-vitro
    • Loftsson, T, Thormar, H, Olafsson, JH, Gunnarsdóttir, TM, Hjaltason, B, Gudmundsson, G. Fatty acid extract from cod-liver oil: activity against herpes simplex virus and enhancement of transdermal delivery of acyclovir in-vitro. Pharm Pharmacol Commun. 1998;4:287-91.
    • (1998) Pharm Pharmacol Commun , vol.4 , pp. 287-291
    • Loftsson, T.1    Thormar, H.2    Olafsson, J.H.3    Gunnarsdóttir, T.M.4    Hjaltason, B.5    Gudmundsson, G.6
  • 33
    • 0023597397 scopus 로고
    • Mode of action of penetration enhancers in human skin
    • Barry, BW. Mode of action of penetration enhancers in human skin. J Control Rel. 1987;6:85-97.
    • (1987) J Control Rel , vol.6 , pp. 85-97
    • Barry, B.W.1
  • 34
    • 0023216223 scopus 로고
    • Mechanism of enhancement of percutaneous absorption of molsidomine by oleic acid
    • Yamada, M, Uda, Y, Tanigawara, Y. Mechanism of enhancement of percutaneous absorption of molsidomine by oleic acid. Chem Pharm Bull. 1987;35:3399-3406.
    • (1987) Chem Pharm Bull , vol.35 , pp. 3399-3406
    • Yamada, M.1    Uda, Y.2    Tanigawara, Y.3
  • 35
    • 0032935073 scopus 로고    scopus 로고
    • Influence of propylene glycol and isopropyl myristate on the in vitro percutaneous penetration of diclofenac sodium from carbopol gels
    • Arellano, A, Santoyo, S, Martín, C, Ygartua, P. Influence of propylene glycol and isopropyl myristate on the in vitro percutaneous penetration of diclofenac sodium from carbopol gels. Eur J Pharm Sci. 1999;7:129-35.
    • (1999) Eur J Pharm Sci , vol.7 , pp. 129-135
    • Arellano, A.1    Santoyo, S.2    Martín, C.3    Ygartua, P.4
  • 36
    • 0034891361 scopus 로고    scopus 로고
    • Combined effect of oleic acid and propylene glycol on the percutaneous penetration of tenoxicam and its retention in the skin
    • Larrucca, E, Arellano, A, Santoyo, S, Ygartua, P. Combined effect of oleic acid and propylene glycol on the percutaneous penetration of tenoxicam and its retention in the skin. Eur J Pharm Biopharm. 2001;52:113-19.
    • (2001) Eur J Pharm Biopharm , vol.52 , pp. 113-119
    • Larrucca, E.1    Arellano, A.2    Santoyo, S.3    Ygartua, P.4
  • 37
    • 0032509907 scopus 로고    scopus 로고
    • Enhanced transdermal delivery of AZT (zidovudine) using iontophoresis and penetration enhancer
    • Oh, SY, Jeong, SY, Park, TG, Lee, JH. Enhanced transdermal delivery of AZT (zidovudine) using iontophoresis and penetration enhancer. J Control Rel. 1998;51:161-68.
    • (1998) J Control Rel , vol.51 , pp. 161-168
    • Oh, S.Y.1    Jeong, S.Y.2    Park, T.G.3    Lee, J.H.4
  • 38
    • 0025264806 scopus 로고
    • Percutaneous penetration of acyclovir through excised hairless mouse and rat skin: Effect of vehicle and percutaneous penetration enhancer
    • Okamoto, H, Muta, K, Hashida, M, Sezaki, H. Percutaneous penetration of acyclovir through excised hairless mouse and rat skin: effect of vehicle and percutaneous penetration enhancer. Pharm Res. 1990;7:64-68.
    • (1990) Pharm Res , vol.7 , pp. 64-68
    • Okamoto, H.1    Muta, K.2    Hashida, M.3    Sezaki, H.4
  • 39
    • 0028873448 scopus 로고
    • Influence of propylene glycol as cosolvent on mechanisms of drug transport from hydrogels
    • Bendas, B, Schmalfuss, U, Neubert, R. Influence of propylene glycol as cosolvent on mechanisms of drug transport from hydrogels. Int J Pharmaceut. 1995;116:19-30.
    • (1995) Int J Pharmaceut , vol.116 , pp. 19-30
    • Bendas, B.1    Schmalfuss, U.2    Neubert, R.3
  • 41
    • 0033065970 scopus 로고    scopus 로고
    • Influence of pharmaceutical gel vehicles containing oleic/sodium oleate combinations on hairless mouse skin, a histological evaluation
    • Sintov, A, Ze'evi, A, Uzan, R, Nyska, A. Influence of pharmaceutical gel vehicles containing oleic/sodium oleate combinations on hairless mouse skin, a histological evaluation. Eur J Pharm Biopharm. 1999;47:299-303.
    • (1999) Eur J Pharm Biopharm , vol.47 , pp. 299-303
    • Sintov, A.1    Ze'evi, A.2    Uzan, R.3    Nyska, A.4
  • 42
    • 0037161329 scopus 로고    scopus 로고
    • Oleic acid, a skin penetration enhancer, affects Langerhans cells and corneocytes
    • Touitou, E, Godin, B, Karl, Y, Bujanover, S, Becker, Y. Oleic acid, a skin penetration enhancer, affects Langerhans cells and corneocytes. J Control Rel. 2002;80:1-7.
    • (2002) J Control Rel , vol.80 , pp. 1-7
    • Touitou, E.1    Godin, B.2    Karl, Y.3    Bujanover, S.4    Becker, Y.5
  • 44
    • 0035850210 scopus 로고    scopus 로고
    • Characterization of the influence of polyol fatty acid esters on the permeation of diclofenac through rat skin
    • Takahashi, K, Sakano, H, Yoshida, M, Numata, N, Mizuno, N. Characterization of the influence of polyol fatty acid esters on the permeation of diclofenac through rat skin. J Control Release. 2001;73:351-58.
    • (2001) J Control Release , vol.73 , pp. 351-358
    • Takahashi, K.1    Sakano, H.2    Yoshida, M.3    Numata, N.4    Mizuno, N.5
  • 45
    • 0024375494 scopus 로고
    • Effect of several enhancers on the skin permeation of water-soluble drugs
    • Okumura, M, Sugibayashi, K, Morimoto, Y. Effect of several enhancers on the skin permeation of water-soluble drugs. Chem Pharm Bull. 1989;37:1375-78.
    • (1989) Chem Pharm Bull , vol.37 , pp. 1375-1378
    • Okumura, M.1    Sugibayashi, K.2    Morimoto, Y.3
  • 46
    • 0036445563 scopus 로고    scopus 로고
    • Effect of fatty acid diesters on permeation of anti-inflammatory drugs through rat skin
    • Takahashi, K, Sakano, H, Numata, N, Kuroda, S, Mizuno, N. Effect of fatty acid diesters on permeation of anti-inflammatory drugs through rat skin. Drug Dev Ind Pharm. 2002;28:1285-94.
    • (2002) Drug Dev Ind Pharm , vol.28 , pp. 1285-1294
    • Takahashi, K.1    Sakano, H.2    Numata, N.3    Kuroda, S.4    Mizuno, N.5
  • 47
    • 0000270186 scopus 로고
    • Drug metabolism
    • Wolff ME, Editor. 5th ed. New York: Wiley-Interscience
    • Testa, B. Drug metabolism. In: Wolff ME, Editor. Burger's Medicinal Chemistry and Drug discovery. Vol. 1, 5th ed. New York: Wiley-Interscience; 1995. p. 129-80.
    • (1995) Burger's Medicinal Chemistry and Drug Discovery , vol.1 , pp. 129-180
    • Testa, B.1
  • 48
    • 0002323166 scopus 로고    scopus 로고
    • Designing prodrugs and bioprecursors. I. Carrier prodrugs
    • Wermuth, CG, editor. Academic
    • Wermuth, CG, Gaignault, JC, Marchandeau, C. Designing prodrugs and bioprecursors. I. Carrier prodrugs. In: Wermuth, CG, editor. The practice of medicinal chemistry, Academic; 1996. p. 671-96,.
    • (1996) The Practice of Medicinal Chemistry , pp. 671-696
    • Wermuth, C.G.1    Gaignault, J.C.2    Marchandeau, C.3
  • 49
    • 0027436644 scopus 로고
    • Naproxen. 1-Alkylazacycloalkan-2-one esters as dermal prodrugs: In vitro evaluation
    • Bonina, FP, Montenegro, L, Guerrera, F. Naproxen. 1-alkylazacycloalkan-2- one esters as dermal prodrugs: in vitro evaluation. Int J Pharm. 1993;100:99-105.
    • (1993) Int J Pharm , vol.100 , pp. 99-105
    • Bonina, F.P.1    Montenegro, L.2    Guerrera, F.3
  • 50
    • 0037221753 scopus 로고    scopus 로고
    • Ketoprofen. 1-Alkylazacycloalkan-2-one esters as dermal prodrugs: In vivo and in vitro evaluations
    • Bonina, F, Santagati, NA, Puglia, C. Ketoprofen. 1-alkylazacycloalkan-2- one esters as dermal prodrugs: in vivo and in vitro evaluations, Drug Dev Ind Pharm. 2003;29:181-90.
    • (2003) Drug Dev Ind Pharm , vol.29 , pp. 181-190
    • Bonina, F.1    Santagati, N.A.2    Puglia, C.3
  • 51
    • 0031743198 scopus 로고    scopus 로고
    • In vitro evaluation of acyloxyalkyl esters as dermal prodrugs of ketoprofen and naproxen
    • Rautio, J, Taipale, H, Gynther, J, Vepsalainen, J, Nevalainen, T, Jarvinen, T. In vitro evaluation of acyloxyalkyl esters as dermal prodrugs of ketoprofen and naproxen. J Pharm Sci. 1998;87:1622-28.
    • (1998) J Pharm Sci , vol.87 , pp. 1622-1628
    • Rautio, J.1    Taipale, H.2    Gynther, J.3    Vepsalainen, J.4    Nevalainen, T.5    Jarvinen, T.6
  • 52
    • 0036158330 scopus 로고    scopus 로고
    • Synthesis, stability and in vitro dermal evaluation of aminocarbonyloxymethyl esters as prodrugs of carboxylic acid agents
    • Mendes, E, Furtado, T, Neres, J, Iley, J, Jarvinen, T, Rautio, J, et al. Synthesis, stability and in vitro dermal evaluation of aminocarbonyloxymethyl esters as prodrugs of carboxylic acid agents. Bioorg Med Chem. 2002;10:809-16.
    • (2002) Bioorg Med Chem , vol.10 , pp. 809-816
    • Mendes, E.1    Furtado, T.2    Neres, J.3    Iley, J.4    Jarvinen, T.5    Rautio, J.6
  • 53
    • 0032803081 scopus 로고    scopus 로고
    • Synthesis and in vitro evaluation of aminoacyloxyalkyl esters of 2-(6-methoxy-2-naphthyl)propionic acid as novel naproxen prodrugs for dermal drug delivery
    • Rautio, J, Nevalainen, T, Taipale, H, Vepsalainen, J, Gynther, J, Pedersen, T, et al. Synthesis and in vitro evaluation of aminoacyloxyalkyl esters of 2-(6-methoxy-2-naphthyl)propionic acid as novel naproxen prodrugs for dermal drug delivery. Pharm Res. 1999;16:1172-78.
    • (1999) Pharm Res , vol.16 , pp. 1172-1178
    • Rautio, J.1    Nevalainen, T.2    Taipale, H.3    Vepsalainen, J.4    Gynther, J.5    Pedersen, T.6
  • 55
    • 0034692169 scopus 로고    scopus 로고
    • Synthesis and in vitro evaluation of novel morpholinyl- And methylpiperazinylacyloxyalkyl prodrugs of 2-(6-methoxy-2-naphthyl)propionic acid (Naproxen) for topical drug delivery
    • Rautio, J, Nevalainen, T, Taipale, H, Vepsalainen, J, Gynther, J, Laine, K, et al. Synthesis and in vitro evaluation of novel morpholinyl- and methylpiperazinylacyloxyalkyl prodrugs of 2-(6-methoxy-2-naphthyl)propionic acid (Naproxen) for topical drug delivery. J Med Chem. 2000;43:1489-94.
    • (2000) J Med Chem , vol.43 , pp. 1489-1494
    • Rautio, J.1    Nevalainen, T.2    Taipale, H.3    Vepsalainen, J.4    Gynther, J.5    Laine, K.6
  • 56
  • 57
    • 0034898142 scopus 로고    scopus 로고
    • In vitro and in vivo evaluation of polyoxyethylene esters as dermal prodrugs of ketoprofen, naproxen and diclofenac
    • Bonina, FP, Puglia, C, Barbuzzi, T, de Caprariis, P, Palagiano, F, Rimoli, MG, et al. In vitro and in vivo evaluation of polyoxyethylene esters as dermal prodrugs of ketoprofen, naproxen and diclofenac. Eur J Pharm Sci. 2001;14:123-34.
    • (2001) Eur J Pharm Sci , vol.14 , pp. 123-134
    • Bonina, F.P.1    Puglia, C.2    Barbuzzi, T.3    De Caprariis, P.4    Palagiano, F.5    Rimoli, M.G.6
  • 58
    • 0242516016 scopus 로고    scopus 로고
    • Synthesis and evaluation of ketorolac ester prodrugs for transdermal delivery
    • Doh, H-J, Cho, W-J, Yong, C-S, Choi, H-G, Kim, JS, Lee, C-H, et al. Synthesis and evaluation of ketorolac ester prodrugs for transdermal delivery. J Pharm Sci. 2003;92:1008-17.
    • (2003) J Pharm Sci , vol.92 , pp. 1008-1017
    • Doh, H.-J.1    Cho, W.-J.2    Yong, C.-S.3    Choi, H.-G.4    Kim, J.S.5    Lee, C.-H.6
  • 59
    • 15044355680 scopus 로고    scopus 로고
    • Ketorolac amide prodrugs for transdermal delivery: Stability and in vitro rat skin permeation studies
    • Kim, B-Y, Doh, H-J, Le, TN, Cho, W-J, Yong, C-S, Choi, H-G, et al. Ketorolac amide prodrugs for transdermal delivery: stability and in vitro rat skin permeation studies. Int J Pharm. 2005;293:193-202.
    • (2005) Int J Pharm , vol.293 , pp. 193-202
    • Kim, B.-Y.1    Doh, H.-J.2    Le, T.N.3    Cho, W.-J.4    Yong, C.-S.5    Choi, H.-G.6
  • 60
    • 0036892908 scopus 로고    scopus 로고
    • Straight-chain naltrexone ester prodrugs: Diffusion and concurrent esterase biotransformation in human skin
    • Stinchcomb, AL, Swaan, PW, Ekabo, O, Harris, KK, Browe, J, Hammell, DC, et al. Straight-chain naltrexone ester prodrugs: diffusion and concurrent esterase biotransformation in human skin. J Pharm Sci. 2002;91:2571-78.
    • (2002) J Pharm Sci , vol.91 , pp. 2571-2578
    • Stinchcomb, A.L.1    Swaan, P.W.2    Ekabo, O.3    Harris, K.K.4    Browe, J.5    Hammell, D.C.6
  • 62
    • 4644278187 scopus 로고    scopus 로고
    • α-Tocopherol pro-vitamins: Synthesis, hydrolysis and accumulation in rabbit ear skin
    • Ostacolo, C, Marra, F, Laneri, S, Sacchi, A, Nicoli, S, Padula, C, et al α-Tocopherol pro-vitamins: synthesis, hydrolysis and accumulation in rabbit ear skin. J Control Release. 2004;99:403-13.
    • (2004) J Control Release , vol.99 , pp. 403-413
    • Ostacolo, C.1    Marra, F.2    Laneri, S.3    Sacchi, A.4    Nicoli, S.5    Padula, C.6
  • 63
    • 0030005178 scopus 로고    scopus 로고
    • Transdermal delivery of 5-fluorouracil (5-FU) by. 1-alkylcarbonyl-5-FU prodrugs
    • Beall, HD, Sloan, KB. Transdermal delivery of 5-fluorouracil (5-FU) by. 1-alkylcarbonyl-5-FU prodrugs. Int J Pharm. 1996;129:203-10.
    • (1996) Int J Pharm , vol.129 , pp. 203-210
    • Beall, H.D.1    Sloan, K.B.2
  • 64
    • 0031938460 scopus 로고    scopus 로고
    • 1-Alkylcarbonyloxymethyl prodrugs of 5-fluorouracil (5-FU): Synthesis, physicochemical properties, and topical delivery of 5-FU
    • Taylor, HE, Sloan, KB.. 1-Alkylcarbonyloxymethyl prodrugs of 5-fluorouracil (5-FU): Synthesis, physicochemical properties, and topical delivery of 5-FU. J Pharm Sci. 1998;87:15-20.
    • (1998) J Pharm Sci , vol.87 , pp. 15-20
    • Taylor, H.E.1    Sloan, K.B.2
  • 65
    • 0037406528 scopus 로고    scopus 로고
    • Topical delivery of 5-fluorouracil (5-FU) by 3-alkylcarbonyloxymethyl-5- FU prodrugs
    • Roberts, WJ, Sloan, KB. Topical delivery of 5-fluorouracil (5-FU) by 3-alkylcarbonyloxymethyl-5-FU prodrugs. J Pharm Sci. 2003;92:1028-36.
    • (2003) J Pharm Sci , vol.92 , pp. 1028-1036
    • Roberts, W.J.1    Sloan, K.B.2
  • 66
    • 12444249581 scopus 로고    scopus 로고
    • Topical delivery of 5-fluorouracil and 6-mercaptopurine by their alkylcarbonyloxymethyl prodrugs from water: Vehicle effects on design of prodrugs
    • Sloan, KB, Wasdo, S, Ezike-Mkparu, U, Murray, T, Nickels, D, Singh, S, et al. Topical delivery of 5-fluorouracil and 6-mercaptopurine by their alkylcarbonyloxymethyl prodrugs from water: vehicle effects on design of prodrugs. Pharm Res. 2003;20:639-45.
    • (2003) Pharm Res , vol.20 , pp. 639-645
    • Sloan, K.B.1    Wasdo, S.2    Ezike-Mkparu, U.3    Murray, T.4    Nickels, D.5    Singh, S.6
  • 67
    • 3042808372 scopus 로고    scopus 로고
    • Topical delivery of a model phenolic drug: Alkyloxycarbonyl prodrugs of acetaminophen
    • Wasdo, SC, Sloan, KB. Topical delivery of a model phenolic drug: alkyloxycarbonyl prodrugs of acetaminophen. Pharm Res. 2004;21:940-46.
    • (2004) Pharm Res , vol.21 , pp. 940-946
    • Wasdo, S.C.1    Sloan, K.B.2
  • 68
    • 0036547775 scopus 로고    scopus 로고
    • Cycloserine fatty acid derivatives as prodrugs: Synthesis, degradation and in vitro skin permeability
    • Tokyo
    • Thorsteinsson, T, Masson, M, Jarvinen, T, Nevalainen, T, Loftsson, T. Cycloserine fatty acid derivatives as prodrugs: synthesis, degradation and in vitro skin permeability. Chem Pharm Bull (Tokyo). 2002;50:554-57.
    • (2002) Chem Pharm Bull , vol.50 , pp. 554-557
    • Thorsteinsson, T.1    Masson, M.2    Jarvinen, T.3    Nevalainen, T.4    Loftsson, T.5
  • 69
    • 0029958121 scopus 로고    scopus 로고
    • Evaluation of stereoselective transdermal transport and concurrent cutaneous hydrolysis of several ester prodrugs of propranolol: Mechanism of stereoselective permeation
    • Ahmed, S, Imai, T, Masaki, O. Evaluation of stereoselective transdermal transport and concurrent cutaneous hydrolysis of several ester prodrugs of propranolol: mechanism of stereoselective permeation. Pharm Res. 1996;13:1524-29.
    • (1996) Pharm Res , vol.13 , pp. 1524-1529
    • Ahmed, S.1    Imai, T.2    Masaki, O.3
  • 70
    • 0037133122 scopus 로고    scopus 로고
    • Percutaneous penetration and skin metabolism of ethylsalicylate- containing agent, TU-2100: In-vitro and in-vivo evaluation in guinea pigs
    • Sintov, AC, Behar-Canetti, C, Friedman, Y, Tamarkin, D. Percutaneous penetration and skin metabolism of ethylsalicylate-containing agent, TU-2100: in-vitro and in-vivo evaluation in guinea pigs. J Control Release. 2002;79:113-22.
    • (2002) J Control Release , vol.79 , pp. 113-122
    • Sintov, A.C.1    Behar-Canetti, C.2    Friedman, Y.3    Tamarkin, D.4
  • 71
    • 19944432512 scopus 로고    scopus 로고
    • RU 58841-myristate - Prodrug development for topical treatment of acne and androgenetic alopecia
    • Munster, U, Nakamura, C, Haberland, A, Jores, K, Mehnert, W, Rummel, S, et al. RU 58841-myristate - prodrug development for topical treatment of acne and androgenetic alopecia. Pharmazie. 2005;60:8-12.
    • (2005) Pharmazie , vol.60 , pp. 8-12
    • Munster, U.1    Nakamura, C.2    Haberland, A.3    Jores, K.4    Mehnert, W.5    Rummel, S.6
  • 72
    • 0342264395 scopus 로고    scopus 로고
    • Lipophilic metronidazole derivatives and their absorption through hairless mouse skin
    • Masson, M, Thorsteinsson, T, Sigurdsson, TH, Loftsson, T. Lipophilic metronidazole derivatives and their absorption through hairless mouse skin. Pharmazie. 2000;55:369-71.
    • (2000) Pharmazie , vol.55 , pp. 369-371
    • Masson, M.1    Thorsteinsson, T.2    Sigurdsson, T.H.3    Loftsson, T.4
  • 73
    • 17644384003 scopus 로고    scopus 로고
    • Vitamin DS-based conjugates for topical treatment of psoriasis: Synthesis, antiproliferative activity, and cutaneous penetration studies
    • Ben-Shabat, S, Benisty, R, Wormser, U, Sintov, A. Vitamin DS-based conjugates for topical treatment of psoriasis: Synthesis, antiproliferative activity, and cutaneous penetration studies. Pharm Res. 2005;22:50-7.
    • (2005) Pharm Res , vol.22 , pp. 50-57
    • Ben-Shabat, S.1    Benisty, R.2    Wormser, U.3    Sintov, A.4
  • 74
    • 0028909356 scopus 로고
    • Cutaneous permeability barrier disruption increases fatty acid synthetic enzyme activity in the epidermis of hairless mice
    • Ottey, KA, Wood, LC, Grunfeld, C, Elias, PM, Feingold, KR. Cutaneous permeability barrier disruption increases fatty acid synthetic enzyme activity in the epidermis of hairless mice. J Invest Dermatol. 1995;104:401-4.
    • (1995) J Invest Dermatol , vol.104 , pp. 401-404
    • Ottey, K.A.1    Wood, L.C.2    Grunfeld, C.3    Elias, P.M.4    Feingold, K.R.5
  • 75
    • 0034932649 scopus 로고    scopus 로고
    • Generation of free fatty acids from phospholipids regulates stratum corneum acidification and integrity
    • Fluhr, JW, Kao, J, Jain, M, Ahn, SK, Feingold, KR, Elias, PM._Generation of free fatty acids from phospholipids regulates stratum corneum acidification and integrity. J Invest Dermatol. 2001;117:44-51.
    • (2001) J Invest Dermatol , vol.117 , pp. 44-51
    • Fluhr, J.W.1    Kao, J.2    Jain, M.3    Ahn, S.K.4    Feingold, K.R.5    Elias, P.M.6
  • 76
    • 0344738769 scopus 로고    scopus 로고
    • The effect of eicosapentaenoic acid on rat lymphocyte proliferation depends upon its position in dietary triacylglycerols
    • Kew, S, Wells, S, Thies, F, McNeill, GP, Quinlan, PT, Clark, GT, et al. The effect of eicosapentaenoic acid on rat lymphocyte proliferation depends upon its position in dietary triacylglycerols. J Nutr. 2003;133: 4238-40.
    • (2003) J Nutr , vol.133 , pp. 4238-4240
    • Kew, S.1    Wells, S.2    Thies, F.3    McNeill, G.P.4    Quinlan, P.T.5    Clark, G.T.6
  • 77
    • 0023870325 scopus 로고
    • A double-blind, randomised, placebo-controlled trial of fish oil in psoriasis
    • Bittiner, SB, Tucker, WF, Cartwrightand I, Bleehen, SS. A double-blind, randomised, placebo-controlled trial of fish oil in psoriasis. Lancet. 1988;1:378-80.
    • (1988) Lancet , vol.1 , pp. 378-380
    • Bittiner, S.B.1    Tucker, W.F.2    Cartwrightand, I.3    Bleehen, S.S.4


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