메뉴 건너뛰기




Volumn 43, Issue 8, 2000, Pages 1489-1494

Synthesis and in vitro evaluation of novel morpholinyl- and methylpiperazinylacyloxyalkyl prodrugs of 2-(6-methoxy,2-naphthyl)propionic acid (naproxen) for topical drug delivery

Author keywords

[No Author keywords available]

Indexed keywords

NAPROXEN;

EID: 0034692169     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm991149s     Document Type: Article
Times cited : (49)

References (34)
  • 1
    • 0026471575 scopus 로고
    • Local Enhanced Topical Delivery (LETD) of drugs: Does it truly exist?
    • McNeill, S. C.; Potts, R. O.; Francoeur, M. L. Local Enhanced Topical Delivery (LETD) of Drugs: Does It Truly Exist? Pharm. Res. 1992, 9, 1422-1427.
    • (1992) Pharm. Res. , vol.9 , pp. 1422-1427
    • McNeill, S.C.1    Potts, R.O.2    Francoeur, M.L.3
  • 2
    • 0030770533 scopus 로고    scopus 로고
    • Pharmacokinetic and local tissue disposition studies of naproxen following topical and systemic administration in dogs and rats
    • Suh, H.; Jun, H. W.; Dzimianski, M. T.; Lu, G. W. Pharmacokinetic and Local Tissue Disposition Studies of Naproxen Following Topical and Systemic Administration in Dogs and Rats. Biopharm. Drug Disp. 1997, 18, 623-633.
    • (1997) Biopharm. Drug Disp. , vol.18 , pp. 623-633
    • Suh, H.1    Jun, H.W.2    Dzimianski, M.T.3    Lu, G.W.4
  • 3
    • 0031939444 scopus 로고    scopus 로고
    • Transdermal delivery and accumulation of indomethacin in subcutaneous tissues in rats
    • Mikulak, S. A.; Vangsness, C. T.; Nimni, M. E. Transdermal Delivery and Accumulation of Indomethacin in Subcutaneous Tissues in Rats. J. Pharm. Pharmacol. 1998, 50, 153-158.
    • (1998) J. Pharm. Pharmacol. , vol.50 , pp. 153-158
    • Mikulak, S.A.1    Vangsness, C.T.2    Nimni, M.E.3
  • 4
    • 0018734930 scopus 로고
    • Naproxen up to date: A review of its pharmacological properties and therapeutic efficacy and use in rheumatic diseases and pain states
    • Brogden, R. N.; Heel, R. C.; Speight, T. M.; Avery, G. S. Naproxen Up to Date: a Review of Its Pharmacological Properties and Therapeutic Efficacy and Use in Rheumatic Diseases and Pain States. Drugs 1979, 18, 241-277.
    • (1979) Drugs , vol.18 , pp. 241-277
    • Brogden, R.N.1    Heel, R.C.2    Speight, T.M.3    Avery, G.S.4
  • 5
    • 0022557527 scopus 로고
    • Skin permeability of various non-steroidal antiinflammatory drugs in man
    • Yano, T.; Nakawaga, A.; Tsuji, M.; Noda, K. Skin Permeability of Various Non-Steroidal Antiinflammatory Drugs in Man. Life Sci. 1986, 39, 1043-1050.
    • (1986) Life Sci. , vol.39 , pp. 1043-1050
    • Yano, T.1    Nakawaga, A.2    Tsuji, M.3    Noda, K.4
  • 7
    • 0028140550 scopus 로고
    • Skin permeability and local tissue concentrations of nonsteroidal antiinflammatory drugs after topical application
    • Singh, P.; Roberts, M. S. Skin Permeability and Local Tissue Concentrations of Nonsteroidal Antiinflammatory Drugs After Topical Application. J. Pharmacol. Exp. Ther. 1994, 268, 144-151.
    • (1994) J. Pharmacol. Exp. Ther. , vol.268 , pp. 144-151
    • Singh, P.1    Roberts, M.S.2
  • 8
    • 0001818318 scopus 로고
    • Prodrugs for dermal delivery: Solubility, molecular size, and functional group effects
    • Sloan, K. B., Ed.; Marcel Dekker, Inc.: New York
    • Kasting, G. B.; Smith, R. L.; Anderson, B. D. Prodrugs for Dermal Delivery: Solubility, Molecular Size, and Functional Group Effects. In Prodrugs, Topical and Ocular Drug Delivery; Sloan, K. B., Ed.; Marcel Dekker, Inc.: New York, 1992; pp 117-161.
    • (1992) Prodrugs, Topical and Ocular Drug Delivery , pp. 117-161
    • Kasting, G.B.1    Smith, R.L.2    Anderson, B.D.3
  • 10
    • 0028004676 scopus 로고
    • Ester des naproxens als potentielle prodrugs zur hautpenetration, 2. Mitt.: Penetrationseigenschaften an exzidierter mäusehaut
    • Weber, H.; Meyer-Trümpener, K.; Lippold, B. C. Ester des Naproxens als Potentielle Prodrugs zur Hautpenetration, 2. Mitt.: Penetrationseigenschaften an Exzidierter Mäusehaut. Arch. Pharm. (Weinheim) 1994, 327, 681-686.
    • (1994) Arch. Pharm. (Weinheim) , vol.327 , pp. 681-686
    • Weber, H.1    Meyer-Trümpener, K.2    Lippold, B.C.3
  • 11
    • 0027436644 scopus 로고
    • Naproxen 1-alkylazacycloalkan-2-one esters as dermal prodrugs: In vitro evaluation
    • Bonina, F. P.; 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
  • 13
    • 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.; Vepsäläinen, J.; Gynther, J.; Pedersen, T.; Järvinen, T. 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, 1172-1178.
    • (1999) Pharm. Res. , vol.16 , pp. 1172-1178
    • Rautio, J.1    Nevalainen, T.2    Taipale, H.3    Vepsäläinen, J.4    Gynther, J.5    Pedersen, T.6    Järvinen, T.7
  • 14
    • 0024502494 scopus 로고
    • Preformulation prodrug research - Chemical and enzymatic hydrolysis kinetics of the glycerol, glycolic acid and morpholino ethyl ester derivatives of a developmental analgesic agent (RS-82917)
    • Gu, L.; Dunn, J.; Dvorak, C. Preformulation Prodrug Research - Chemical and Enzymatic Hydrolysis Kinetics of the Glycerol, Glycolic Acid and Morpholino Ethyl Ester Derivatives of a Developmental Analgesic Agent (RS-82917). Drug Dev. Ind. Pharm. 1989, 15, 209-221.
    • (1989) Drug Dev. Ind. Pharm. , vol.15 , pp. 209-221
    • Gu, L.1    Dunn, J.2    Dvorak, C.3
  • 15
    • 0027200613 scopus 로고
    • Synthesis and evaluation of morpholinoalkyl ester prodrugs of indomethacin and naproxen
    • Tammara, V. K.; Narurkar, M. M.; Crider, A. M.; Khan, M. A. Synthesis and Evaluation of Morpholinoalkyl Ester Prodrugs of Indomethacin and Naproxen. Pharm.Res. 1993, 10, 1191-1199.
    • (1993) Pharm.Res. , vol.10 , pp. 1191-1199
    • Tammara, V.K.1    Narurkar, M.M.2    Crider, A.M.3    Khan, M.A.4
  • 16
    • 0028289775 scopus 로고
    • Morpholinoalkyl ester prodrugs of diclofenac: Synthesis, in vitro and in vivo evaluation
    • Tammara, V. K.; Narurkar, M. M.; Crider, A. M.; Khan, M. A. Morpholinoalkyl Ester Prodrugs of Diclofenac: Synthesis, In Vitro and In Vivo Evaluation. J. Pharm. Sci. 1994, 83, 644-648.
    • (1994) J. Pharm. Sci. , vol.83 , pp. 644-648
    • Tammara, V.K.1    Narurkar, M.M.2    Crider, A.M.3    Khan, M.A.4
  • 17
    • 0029880941 scopus 로고    scopus 로고
    • Derivatives of dexanabinol. II. Salts of amino acid esters containing tertiary and quaternary heterocyclic nitrogen with increased water-solubility
    • Pop, E.; Soti, F.; Brewster, M. E.; Barenholz, Y.; Korablyov, V.; Mechoulam, R.; Nadler, V.; Biegon, A. Derivatives of Dexanabinol. II. Salts of Amino Acid Esters Containing Tertiary and Quaternary Heterocyclic Nitrogen with Increased Water-Solubility. Pharm. Res. 1996, 13, 469-475.
    • (1996) Pharm. Res. , vol.13 , pp. 469-475
    • Pop, E.1    Soti, F.2    Brewster, M.E.3    Barenholz, Y.4    Korablyov, V.5    Mechoulam, R.6    Nadler, V.7    Biegon, A.8
  • 18
    • 0024577945 scopus 로고
    • The utilization of prodrugs to enhance transdermal absorption of testosterone, deoxycorticosterone & indomethacin
    • Milosovich, S. M.; Hussain, A. A.; Hussain, M.; Dittert, L. The Utilization of Prodrugs to Enhance Transdermal Absorption of Testosterone, Deoxycorticosterone & Indomethacin. Prog. Clin. Biol. Res. 1989, 292, 273-277.
    • (1989) Prog. Clin. Biol. Res. , vol.292 , pp. 273-277
    • Milosovich, S.M.1    Hussain, A.A.2    Hussain, M.3    Dittert, L.4
  • 19
    • 0021187194 scopus 로고
    • Mannich base derivatives of theophylline and 5-fluorouracil: Syntheses, properties and topical delivery characteristics
    • Sloan, K. B.; Koch, S. A. M.; Siver, K. G. Mannich Base Derivatives of Theophylline and 5-Fluorouracil: Syntheses, Properties and Topical Delivery Characteristics. Int. J. Pharm. 1984, 21, 251-264.
    • (1984) Int. J. Pharm. , vol.21 , pp. 251-264
    • Sloan, K.B.1    Koch, S.A.M.2    Siver, K.G.3
  • 20
    • 0031543964 scopus 로고    scopus 로고
    • Ibuprofen heterocyclic esters as dermal prodrugs in vitro evaluation
    • Chang, S. Y.; Park, S. B.; Jung, J. H.; Shon, S. I.; Yoon, H. J. Ibuprofen Heterocyclic Esters as Dermal Prodrugs In Vitro Evaluation. STP Pharm. Sci. 1997, 7, 315-319.
    • (1997) STP Pharm. Sci. , vol.7 , pp. 315-319
    • Chang, S.Y.1    Park, S.B.2    Jung, J.H.3    Shon, S.I.4    Yoon, H.J.5
  • 21
    • 0032104465 scopus 로고    scopus 로고
    • 7-Alkylcarbonyloxymethyl prodrugs of theophylline: Topical delivery of theophylline
    • Kerr, D.; Roberts, W.; Tebbett, I.; Sloan, K. B. 7-Alkylcarbonyloxymethyl Prodrugs of Theophylline: Topical Delivery of Theophylline. Int. J. Pharm. 1998, 167, 37-48.
    • (1998) Int. J. Pharm. , vol.167 , pp. 37-48
    • Kerr, D.1    Roberts, W.2    Tebbett, I.3    Sloan, K.B.4
  • 22
    • 0031938460 scopus 로고    scopus 로고
    • 1-Alkylcarbonyloxymethyl prodrugs of 5-fluorouracil (5-FU): Synthesis, physicochemical properties, and topical delivery of 5-FU
    • Taylor, H. E.; Sloan, K. B. 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
  • 23
    • 0032459066 scopus 로고    scopus 로고
    • The selection and design of topical and transdermal agents: A review
    • Hadgraft, J.; Pugh, W. J. The Selection and Design of Topical and Transdermal Agents: A Review. J. Invest. Dermatol. Symp. Proc. 1998, 3, 131-135.
    • (1998) J. Invest. Dermatol. Symp. Proc. , vol.3 , pp. 131-135
    • Hadgraft, J.1    Pugh, W.J.2
  • 25
    • 0025917222 scopus 로고
    • O,O′-(1,4-xylene) bispilocarpic acid esters as new potential double prodrugs of pilocarpine for improved ocular delivery. II. Physicochemical properties, stability, solubility and enzymatic hydrolysis
    • Järvinen, T.; Suhonen, P.; Urtti, A.; Peura, P. O,O′-(1,4-xylene) Bispilocarpic Acid Esters as New Potential Double Prodrugs of Pilocarpine for Improved Ocular Delivery. II. Physicochemical Properties, Stability, Solubility and Enzymatic Hydrolysis. Int. J. Pharm. 1991, 75, 259-269.
    • (1991) Int. J. Pharm. , vol.75 , pp. 259-269
    • Järvinen, T.1    Suhonen, P.2    Urtti, A.3    Peura, P.4
  • 26
    • 0024603946 scopus 로고
    • The double prodrug concept and its applications
    • Bundgaard, H. The Double Prodrug Concept and Its Applications. Adv. Drug Deliv. Rev. 1989, 3, 39-65.
    • (1989) Adv. Drug Deliv. Rev. , vol.3 , pp. 39-65
    • Bundgaard, H.1
  • 27
    • 0024553048 scopus 로고
    • Prodrugs for dermal delivery
    • Sloan, K. B. Prodrugs for Dermal Delivery. Adv. Drug Deliv. Rev. 1989, 3, 67-101.
    • (1989) Adv. Drug Deliv. Rev. , vol.3 , pp. 67-101
    • Sloan, K.B.1
  • 30
    • 0343430036 scopus 로고
    • Substituted α-(4-morpholinyl)-acetonitriles and related compounds
    • Henry, R. A.; Dehn, W. N. Substituted α-(4-Morpholinyl)-acetonitriles and Related Compounds. J. Am. Chem. Soc. 1950, 72, 2804-2806.
    • (1950) J. Am. Chem. Soc. , vol.72 , pp. 2804-2806
    • Henry, R.A.1    Dehn, W.N.2
  • 31
    • 84985232944 scopus 로고
    • Diphenylboron chelates of α-(dialkylamino)carboxylic acids and their N-oxides
    • Kliegel, W.; Graumann, J. Diphenylboron Chelates of α-(Dialkylamino)carboxylic Acids and Their N-oxides. Liebigs Ann. Chem. 1983, 6, 950-961.
    • (1983) Liebigs Ann. Chem. , vol.6 , pp. 950-961
    • Kliegel, W.1    Graumann, J.2
  • 32
    • 0016268448 scopus 로고
    • Water-soluble derivatives of 3-oxy-substituted 1,4-benzodiazepines
    • Nudelman, A.; McCaully, R. J.; Bell, S. C. Water-Soluble Derivatives of 3-Oxy-substituted 1,4-Benzodiazepines. J. Pharm. Sci. 1974, 63, 1880-1885.
    • (1974) J. Pharm. Sci. , vol.63 , pp. 1880-1885
    • Nudelman, A.1    McCaully, R.J.2    Bell, S.C.3
  • 34
    • 0001313608 scopus 로고
    • Absorption of drugs through the skin
    • Eichler, O., Farah, A., Herken, H., Welch, A. D., Eds.; Springer-Verlag: Berlin
    • Katz, M.; Poulsen, B. J. Absorption of Drugs Through the Skin. In Handbook of Experimental Pharmacology; Eichler, O., Farah, A., Herken, H., Welch, A. D., Eds.; Springer-Verlag: Berlin, 1971; pp 103-174.
    • (1971) Handbook of Experimental Pharmacology , pp. 103-174
    • Katz, M.1    Poulsen, B.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.