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Volumn 30, Issue 4, 1998, Pages 787-807

Design of intramolecularly activated prodrugs

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOBENZAMIDE; AMIDE; AMINE; BENZAMIDE DERIVATIVE; CARBAMIC ACID DERIVATIVE; CARBAMIC ACID ESTER; CARBOXYLIC ACID DERIVATIVE; HYDROXYL GROUP; MEQUINOL; PHENOL DERIVATIVE; PILOCARPIC ACID; PILOCARPINE; PRODRUG; PROPIONAMIDE DERIVATIVE;

EID: 0031726953     PISSN: 03602532     EISSN: None     Source Type: Journal    
DOI: 10.3109/03602539808996330     Document Type: Review
Times cited : (35)

References (31)
  • 2
    • 0345712954 scopus 로고
    • Drug latentiation
    • E. Jucker, ed., Birkhäuser, Basel
    • N. J. Harper, Drug latentiation, in Progress in Drug Research (E. Jucker, ed.), Birkhäuser, Basel, 1962, Vol. 4, pp. 221-294.
    • (1962) Progress in Drug Research , vol.4 , pp. 221-294
    • Harper, N.J.1
  • 3
    • 0021800252 scopus 로고
    • Prodrugs: Do they have advantages in clinical practice?
    • V. J. Stella, W. N. A. Charman, and V. H. Naringrekar, Prodrugs: Do they have advantages in clinical practice? Drugs, 29, 455-473 (1985).
    • (1985) Drugs , vol.29 , pp. 455-473
    • Stella, V.J.1    Charman, W.N.A.2    Naringrekar, V.H.3
  • 6
    • 0004579318 scopus 로고
    • Designing prodrugs and bioprecursors
    • G. Jolles and K. R. H. Woolridge, eds., Academic Press, London
    • C. G. Wermuth, Designing prodrugs and bioprecursors, in Drug Design: Fact or Fantasy? (G. Jolles and K. R. H. Woolridge, eds.), Academic Press, London, 1984, pp. 47-72.
    • (1984) Drug Design: Fact or Fantasy? , pp. 47-72
    • Wermuth, C.G.1
  • 7
    • 0021778490 scopus 로고
    • Drug and Enzyme Targeting
    • Academic Press, Orlando, FL
    • K. J. Widder and R. Green (eds.), Drug and Enzyme Targeting, Methods in Enzymology, Volume 112, Academic Press, Orlando, FL, 1985.
    • (1985) Methods in Enzymology , vol.112
    • Widder, K.J.1    Green, R.2
  • 13
    • 0029865447 scopus 로고    scopus 로고
    • Prodrugs revisited - The "ad hoc" approach as a complement to ligand design
    • B. Testa and J. Caldwell, Prodrugs revisited - The "ad hoc" approach as a complement to ligand design, Med. Res. Rev., 16, 233-241 (1996).
    • (1996) Med. Res. Rev. , vol.16 , pp. 233-241
    • Testa, B.1    Caldwell, J.2
  • 14
    • 37049068671 scopus 로고
    • Stereochemical studies. Part 112. Geometrical dependence of intramolecular catalysis in the hydrolysis and aminolysis of aryl esters
    • M. I. Page, D. Render, and G. Bernath, Stereochemical studies. Part 112. Geometrical dependence of intramolecular catalysis in the hydrolysis and aminolysis of aryl esters, J. Chem. Soc. Perkin Trans. II, 867-871 (1986).
    • (1986) J. Chem. Soc. Perkin Trans. , vol.2 , pp. 867-871
    • Page, M.I.1    Render, D.2    Bernath, G.3
  • 15
    • 0021366102 scopus 로고
    • Prodrugs as drug delivery systems XXVII. Chemical stability and bioavailability of a water-soluble prodrug of metronidazole for parenteral administration
    • H. Bundgaard, C. Larsen, and E. Arnold, Prodrugs as drug delivery systems XXVII. Chemical stability and bioavailability of a water-soluble prodrug of metronidazole for parenteral administration, Int. J. Pharmaceut., 18, 79-87 (1984).
    • (1984) Int. J. Pharmaceut. , vol.18 , pp. 79-87
    • Bundgaard, H.1    Larsen, C.2    Arnold, E.3
  • 16
    • 0025027549 scopus 로고
    • Structure-reactivity relationships in the chemical hydrolysis of prodrug esters of nicotinic acid
    • G. N. Wernly-Chung, J. M. Mayer, A. Tsantili-Kakoulidou, and B. Testa, Structure-reactivity relationships in the chemical hydrolysis of prodrug esters of nicotinic acid, Int. J. Pharmaceut., 63, 129-134 (1990).
    • (1990) Int. J. Pharmaceut. , vol.63 , pp. 129-134
    • Wernly-Chung, G.N.1    Mayer, J.M.2    Tsantili-Kakoulidou, A.3    Testa, B.4
  • 17
    • 0030808023 scopus 로고    scopus 로고
    • Prodrug strategies based on intramolecular cyclization reactions
    • D. Shan, M. G. Nicolaou, R. T. Borchardt, and B. Wang, Prodrug strategies based on intramolecular cyclization reactions, J. Pharm. Sci., 86, 765-767 (1997).
    • (1997) J. Pharm. Sci. , vol.86 , pp. 765-767
    • Shan, D.1    Nicolaou, M.G.2    Borchardt, R.T.3    Wang, B.4
  • 18
    • 0025117883 scopus 로고
    • Cyclization-activated prodrugs. Basic esters of 5-bromo-2′-deoxyuridine
    • W. S. Saari, J. E. Schwering, P. A. Lyle, S. J. Smith, and E. L. Engelhardt, Cyclization-activated prodrugs. Basic esters of 5-bromo-2′-deoxyuridine, J. Med. Chem., 33, 2590-2595 (1990).
    • (1990) J. Med. Chem. , vol.33 , pp. 2590-2595
    • Saari, W.S.1    Schwering, J.E.2    Lyle, P.A.3    Smith, S.J.4    Engelhardt, E.L.5
  • 20
    • 0027964507 scopus 로고
    • Evaluation of phenyl carbamates of ethyl diamines as cyclization-activated prodrug forms for protecting phenols against first-pass metabolism
    • K. F. Thomsen, F. Strøm, B. V. Sforzini, M. Begtrup, and N. Mørk, Evaluation of phenyl carbamates of ethyl diamines as cyclization-activated prodrug forms for protecting phenols against first-pass metabolism, Int. J. Pharmaceut., 112, 143-152 (1994).
    • (1994) Int. J. Pharmaceut. , vol.112 , pp. 143-152
    • Thomsen, K.F.1    Strøm, F.2    Sforzini, B.V.3    Begtrup, M.4    Mørk, N.5
  • 21
    • 0027467645 scopus 로고
    • Cyclization-activated phenyl carbamate prodrug forms for protecting phenols against first-pass metabolism
    • K. F. Thomsen and H. Bundgaard, Cyclization-activated phenyl carbamate prodrug forms for protecting phenols against first-pass metabolism, Int. J. Pharmaceut., 91, 39-49 (1993).
    • (1993) Int. J. Pharmaceut. , vol.91 , pp. 39-49
    • Thomsen, K.F.1    Bundgaard, H.2
  • 22
    • 0029147594 scopus 로고
    • Hemiesters of aliphatic dicarboxylic acids as cyclization-activated prodrug forms for protecting phenols against first-pass metabolism
    • K. Fredholt, N. Mørk, and M. Begtrup, Hemiesters of aliphatic dicarboxylic acids as cyclization-activated prodrug forms for protecting phenols against first-pass metabolism, Int. J. Pharmaceut., 123, 209-216 (1995).
    • (1995) Int. J. Pharmaceut. , vol.123 , pp. 209-216
    • Fredholt, K.1    Mørk, N.2    Begtrup, M.3
  • 23
    • 0028877064 scopus 로고
    • Cyclization-activated prodrugs: N-(Substituted 2-hydroxyphenyl and 2-hydroxypropyl)carbamates based on ring-opened derivatives of active benzoxazolones and oxazolidinones as mutual prodrugs of acetaminophen
    • A. Vigroux, M. Bergon, and C. Zedde, Cyclization-activated prodrugs: N-(Substituted 2-hydroxyphenyl and 2-hydroxypropyl)carbamates based on ring-opened derivatives of active benzoxazolones and oxazolidinones as mutual prodrugs of acetaminophen, J. Med. Chem., 38, 3983-3994 (1995).
    • (1995) J. Med. Chem. , vol.38 , pp. 3983-3994
    • Vigroux, A.1    Bergon, M.2    Zedde, C.3
  • 24
    • 0022543135 scopus 로고
    • Pilocarpine prodrugs. II. Synthesis, stability, bioconversion, and physicochemical properties of sequentially labile pilocarpine acid diesters
    • H. Bundgaard, E. Falch, C. Larsen, G. L. Mosher, and T. J. Mikkelson, Pilocarpine prodrugs. II. Synthesis, stability, bioconversion, and physicochemical properties of sequentially labile pilocarpine acid diesters, J. Pharm. Sci., 75, 775-783 (1986).
    • (1986) J. Pharm. Sci. , vol.75 , pp. 775-783
    • Bundgaard, H.1    Falch, E.2    Larsen, C.3    Mosher, G.L.4    Mikkelson, T.J.5
  • 25
    • 0022576486 scopus 로고
    • Prodrugs as drug delivery systems. 42. 2-Hydroxymethylbenzamides and 2-acyloxymethylbenzamides as potential prodrug forms for amines
    • N. M. Nielsen and H. Bundgaard, Prodrugs as drug delivery systems. 42. 2-Hydroxymethylbenzamides and 2-acyloxymethylbenzamides as potential prodrug forms for amines, Int. J. Pharmaceut., 29, 9-18 (1986).
    • (1986) Int. J. Pharmaceut. , vol.29 , pp. 9-18
    • Nielsen, N.M.1    Bundgaard, H.2
  • 26
    • 0025907182 scopus 로고
    • Amine prodrugs which utilize hydroxy amide lactonization. II. a potential esterase-sensitive amide prodrug
    • K. L. Amsberry, A. E. Gerstenberger, and R. T. Borchardt, Amine prodrugs which utilize hydroxy amide lactonization. II. A potential esterase-sensitive amide prodrug, Pharm. Res., 8, 455-461 (1991).
    • (1991) Pharm. Res. , vol.8 , pp. 455-461
    • Amsberry, K.L.1    Gerstenberger, A.E.2    Borchardt, R.T.3
  • 27
    • 0029887595 scopus 로고    scopus 로고
    • Chemical feasibility studies of a potential coumarin-based prodrug system
    • B. Wang, H. Zhang, and W. Wang, Chemical feasibility studies of a potential coumarin-based prodrug system, Bioorg. Med. Chem. Lett., 6, 945-950 (1996).
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 945-950
    • Wang, B.1    Zhang, H.2    Wang, W.3
  • 28
    • 0031041493 scopus 로고    scopus 로고
    • Esterase-sensitive cyclic prodrugs of peptides: Evaluation of a phenylpropionic acid promoiety in a model hexapeptide
    • G. M. Pauletti, S. Gangwar, B. Wang, and R. T. Borchardt, Esterase-sensitive cyclic prodrugs of peptides: Evaluation of a phenylpropionic acid promoiety in a model hexapeptide, Pharm. Res., 14, 11-17 (1997).
    • (1997) Pharm. Res. , vol.14 , pp. 11-17
    • Pauletti, G.M.1    Gangwar, S.2    Wang, B.3    Borchardt, R.T.4
  • 29
    • 0030568115 scopus 로고    scopus 로고
    • Coumarin-based prodrugs 2. Synthesis and bioreversibility studies of an esterase-sensitive cyclic prodrug of DADLE, an opioid peptide
    • B. Wang, W. Wang, H. Zhang, D. Shan, and T. D. Smith, Coumarin-based prodrugs 2. Synthesis and bioreversibility studies of an esterase-sensitive cyclic prodrug of DADLE, an opioid peptide, Bioorg. Med. Chem. Lett., 6, 2823-2826 (1996).
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 2823-2826
    • Wang, B.1    Wang, W.2    Zhang, H.3    Shan, D.4    Smith, T.D.5
  • 30
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • C. A. Lipinski, F. Lombardo, B. W. Dominy, and P. J. Feeney, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Deliv. Rev., 23, 3-25 (1997).
    • (1997) Adv. Drug Deliv. Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.