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Volumn 15, Issue 3, 1998, Pages 434-441

Stability of alkoxycarbonylamidine prodrugs

Author keywords

Alkoxycarbonylamidine; Ester; GPII(b)III(a); Peptidomimetic stability; pH rate profile; Prodrug

Indexed keywords

AMIDINE; ESTER; PRODRUG;

EID: 0031900489     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1011928415808     Document Type: Article
Times cited : (14)

References (34)
  • 1
    • 0024603946 scopus 로고
    • The double prodrug concept and its applications
    • H. Buundgaard. The double prodrug concept and its applications. Adv. Drug Delivery Rev. 3:39-65 (1989).
    • (1989) Adv. Drug Delivery Rev. , vol.3 , pp. 39-65
    • Buundgaard, H.1
  • 2
    • 77956854345 scopus 로고
    • Prodrugs and site-specific chemical delivery systems
    • Allen, ed. Academic Press. New York
    • N. Bodor and J. J. Kaminski. Prodrugs and site-specific chemical delivery systems. In: Allen, ed. Annual Reports in Medicinal Chemistry, Academic Press. New York, 1987, Vol. 22, pp. 303-313.
    • (1987) Annual Reports in Medicinal Chemistry , vol.22 , pp. 303-313
    • Bodor, N.1    Kaminski, J.J.2
  • 3
    • 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. 86:765-7 (1997).
    • (1997) J. Pharm. Sci. , vol.86 , pp. 765-767
    • Shan, D.1    Nicolaou, M.G.2    Borchardt, R.T.3    Wang, B.4
  • 4
  • 7
    • 0018124571 scopus 로고
    • Gastrointestinal absorption. II. Formulation factors affecting drug bioavailability
    • Publ. Health
    • J. Blanchard. Gastrointestinal absorption. II. Formulation factors affecting drug bioavailability. Amer. J. Pharm. Sci. Supp. Publ. Health 150:132-151 (1978).
    • (1978) Amer. J. Pharm. Sci. Supp. , vol.150 , pp. 132-151
    • Blanchard, J.1
  • 10
    • 0029748299 scopus 로고    scopus 로고
    • Fosphenytoin: A novel phenytoin prodrug
    • B. A. Boucher. Fosphenytoin: A novel phenytoin prodrug. Pharmacotherapy 16:771-91 (1996).
    • (1996) Pharmacotherapy , vol.16 , pp. 771-791
    • Boucher, B.A.1
  • 11
    • 0023637601 scopus 로고
    • New perspectives in cell adhesion: RGD and integrins
    • E. Rouslahti and M. D. Pierschbacher. New perspectives in cell adhesion: RGD and integrins. Science 238:491-497 (1987).
    • (1987) Science , vol.238 , pp. 491-497
    • Rouslahti, E.1    Pierschbacher, M.D.2
  • 12
    • 0027302232 scopus 로고
    • Intravenous and endobronchial administration of G4120, a cyclic Arg-Gly-Asp-containing platelet GPIIb/IIIa receptor-blocking pentapeptide, enhances and sustains coronary arterial thrombolysis with rt-PA in a canine preparation
    • T. Yasuda, H. K. Gold, C. Kohmura, et al. Intravenous and endobronchial administration of G4120, a cyclic Arg-Gly-Asp-containing platelet GPIIb/IIIa receptor-blocking pentapeptide, enhances and sustains coronary arterial thrombolysis with rt-PA in a canine preparation. Arteroscl. Thromb. 13:738-747 (1993).
    • (1993) Arteroscl. Thromb. , vol.13 , pp. 738-747
    • Yasuda, T.1    Gold, H.K.2    Kohmura, C.3
  • 14
    • 0027964423 scopus 로고
    • From peptide to non-peptide. 2. The de Novo design of potent, non-peptidal inhibots of platelet aggregation based on a benzodiazepinedione scaffold
    • R. S. McDowell, B. K. Blackburn, T. R. Gadek, et al. From peptide to non-peptide. 2. The de Novo design of potent, non-peptidal inhibots of platelet aggregation based on a benzodiazepinedione scaffold. J. Am. Chem. Soc. 116:5077-5083 (1994).
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 5077-5083
    • McDowell, R.S.1    Blackburn, B.K.2    Gadek, T.R.3
  • 15
    • 2242477091 scopus 로고
    • Use of a monoclonal antibody direct-edagainst the platelet glycoprotein IIbIIIa in high-risk coronary angioplasty
    • The EPIC Investigators. Use of a monoclonal antibody direct-edagainst the platelet glycoprotein IIbIIIa in high-risk coronary angioplasty. New Engl. J. Med. 330:956-1007 (1994).
    • (1994) New Engl. J. Med. , vol.330 , pp. 956-1007
  • 16
    • 9344236530 scopus 로고    scopus 로고
    • Orally active fibrinogen receptor antagonists. 2. Amidoximes as prodrugs of amidines
    • M
    • T. Weller, L. Alig, M. Beresini M, et al. Orally active fibrinogen receptor antagonists. 2. Amidoximes as prodrugs of amidines. J. Med. Chem. 39:3139-3147 (1996).
    • (1996) J. Med. Chem. , vol.39 , pp. 3139-3147
    • Weller, T.1    Alig, L.2    Beresini, M.3
  • 17
    • 0000153966 scopus 로고
    • Rates of hydrolysis of carbamate and carbonate esters in alkaline solution
    • L. W. Dirtert and T. Higuchi. Rates of hydrolysis of carbamate and carbonate esters in alkaline solution. J. Pharm. Sci. 52:852-857 (1963).
    • (1963) J. Pharm. Sci. , vol.52 , pp. 852-857
    • Dirtert, L.W.1    Higuchi, T.2
  • 18
    • 37049132783 scopus 로고
    • Elimination-addition mechanism for the hydrolysis of carbamates. Trapping of an isocyanate intermediate by an o-amino-group
    • A. F. Hegarty and L. N. Frost. Elimination-addition mechanism for the hydrolysis of carbamates. Trapping of an isocyanate intermediate by an o-amino-group. J. Chem. Soc. Perkin Trans II: 1719-1728 (1973).
    • (1973) J. Chem. Soc. Perkin Trans II , pp. 1719-1728
    • Hegarty, A.F.1    Frost, L.N.2
  • 19
    • 0005910343 scopus 로고
    • The question of amide group participation in carbamate hydrolysis
    • A. F. Hegarty, L. N. Frost, J. H. Coy. The question of amide group participation in carbamate hydrolysis. J. Org. Chem. 39:1089-1093 (1974).
    • (1974) J. Org. Chem. , vol.39 , pp. 1089-1093
    • Hegarty, A.F.1    Frost, L.N.2    Coy, J.H.3
  • 20
    • 0005188683 scopus 로고
    • Kinetics and mechanism of hydrolysis of 1-Naphthyl N- Methyl- and N,N-Dimethylcarbamates. Collection Czechoslov
    • T. Vontor, J. Socha. and M. Vecera. Kinetics and mechanism of hydrolysis of 1-Naphthyl N-Methyl-and N,N-Dimethylcarbamates. Collection Czechoslov. Chem. Commun. 37:2183-2196 (1972).
    • (1972) Chem. Commun. , vol.37 , pp. 2183-2196
    • Vontor, T.1    Socha, J.2    Vecera, M.3
  • 21
    • 0343316485 scopus 로고
    • Kinetics and mechanism of hydrolysis of substituted phenyl carbamates. Collection Czechoslov
    • T. Vontor and M. Vecera. Kinetics and mechanism of hydrolysis of substituted phenyl carbamates. Collection Czechoslov. Chem. Commun. 38:516-522 (1973).
    • (1973) Chem. Commun. , vol.38 , pp. 516-522
    • Vontor, T.1    Vecera, M.2
  • 22
    • 0000932724 scopus 로고
    • Mechanistic interpretation of pH-rate profiles
    • G. M. Loudon. Mechanistic interpretation of pH-rate profiles. J. Chem. Educ. 68:973-84 (1991).
    • (1991) J. Chem. Educ. , vol.68 , pp. 973-984
    • Loudon, G.M.1
  • 23
    • 0023127188 scopus 로고
    • Nonsteroidal anti-psoriatic prodrugs: Hydrolysis and aminolysis of naphthyl esters in aqueous solution
    • M. F. Powell, A. Becker, A. Magill. Nonsteroidal anti-psoriatic prodrugs: Hydrolysis and aminolysis of naphthyl esters in aqueous solution. Int. J. Pharmaceutics 35:61-71 (1987).
    • (1987) Int. J. Pharmaceutics , vol.35 , pp. 61-71
    • Powell, M.F.1    Becker, A.2    Magill, A.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
  • 27
    • 0015212957 scopus 로고
    • Plasma esterase activity and the metabolism of drugs with ester groups
    • B. LaDu. Plasma esterase activity and the metabolism of drugs with ester groups. Ann. N. Y. Acad. Sci. 179:684-694 (1993).
    • (1993) Ann. N. Y. Acad. Sci. , vol.179 , pp. 684-694
    • LaDu, B.1
  • 28
    • 0021996062 scopus 로고
    • Clinical significance of esterases in man
    • F. W. Williams. Clinical significance of esterases in man. Clin. Pharmacokin. 10:392-403 (1985).
    • (1985) Clin. Pharmacokin. , vol.10 , pp. 392-403
    • Williams, F.W.1
  • 29
    • 0015399564 scopus 로고
    • Intestinal hydrolysis, metabolism and transport of a pesticidal carbamate in pH 6.5 medium
    • J. C. Pekas. Intestinal hydrolysis, metabolism and transport of a pesticidal carbamate in pH 6.5 medium. Toxicol. Appl. Pharmacol. 23:62-70 (1972).
    • (1972) Toxicol. Appl. Pharmacol. , vol.23 , pp. 62-70
    • Pekas, J.C.1
  • 30
    • 0018386988 scopus 로고
    • Species difference and characterization of intestinal esterase on the hydrolyzing activity of ester-type drugs
    • M. Inoue, M. Morikawa, M. Tsuboi, and M. Sugiura. Species difference and characterization of intestinal esterase on the hydrolyzing activity of ester-type drugs. Japan J. Pharmacol. 29:9-16 (1979).
    • (1979) Japan J. Pharmacol. , vol.29 , pp. 9-16
    • Inoue, M.1    Morikawa, M.2    Tsuboi, M.3    Sugiura, M.4
  • 31
    • 0015542179 scopus 로고
    • In vitro and in vivo hydrolysis of 4-benzoylphenyl N- Methylcarbamate
    • L. W. Brown and A. A. Forist. In vitro and in vivo hydrolysis of 4-benzoylphenyl N-methylcarbamate. J. Pharm. Sci. 62:145-146 (1973).
    • (1973) J. Pharm. Sci. , vol.62 , pp. 145-146
    • Brown, L.W.1    Forist, A.A.2
  • 32
    • 0026085214 scopus 로고
    • Carbamate ester prodrugs of dopaminergic compounds: Synthesis, stability, and bioconversion
    • K. T. Hansen, P. Faarup, and H. Bundgaard. Carbamate ester prodrugs of dopaminergic compounds: Synthesis, stability, and bioconversion. J. Pharm. Sci. 80:793-798 (1991).
    • (1991) J. Pharm. Sci. , vol.80 , pp. 793-798
    • Hansen, K.T.1    Faarup, P.2    Bundgaard, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.