메뉴 건너뛰기




Volumn 13, Issue 3, 2009, Pages 338-344

Prodrugs: bridging pharmacodynamic/pharmacokinetic gaps

Author keywords

[No Author keywords available]

Indexed keywords

4 ACETAMIDO 5 AMINO 3 (1 ETHYLPROPOXY) 1 CYCLOHEXENE 1 CARBOXYLIC ACID; 6,7 DIHYDRO 2 NITRO 6 (4 TRIFLUOROMETHOXYBENZYLOXY) 5H IMIDAZO[2,1 B][1,3]OXAZINE; ADEFOVIR; ADEFOVIR DIPIVOXIL; CAPECITABINE; CLOPIDOGREL; FLUOROURACIL; ISOTAXEL; METRONIDAZOLE; OSELTAMIVIR; PACLITAXEL; PRADEFOVIR; PRASUGREL; PRODRUG; TIRAPAZAMINE; UNCLASSIFIED DRUG; ZANAMIVIR;

EID: 67649849648     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbpa.2009.04.620     Document Type: Review
Times cited : (79)

References (41)
  • 1
    • 67649392788 scopus 로고    scopus 로고
    • Testa B, Krämer SD: The biochemistry of drug metabolism - an introduction. Part 5. Metabolism and bioactivity. Chem Biodivers 2009, 6: in press. An extensive (90 pages), structured and didactic review placing prodrugs in the broader context of metabolic activation and inactivation, toxification, and detoxification.
    • Testa B, Krämer SD: The biochemistry of drug metabolism - an introduction. Part 5. Metabolism and bioactivity. Chem Biodivers 2009, 6: in press. An extensive (90 pages), structured and didactic review placing prodrugs in the broader context of metabolic activation and inactivation, toxification, and detoxification.
  • 2
    • 40149088986 scopus 로고    scopus 로고
    • Prodrugs: design and clinical applications
    • A well-organized, well-written, and information-rich review on the design of prodrugs and their clinical objectives.
    • Raito J., Kumpulainen H., Heimbach T., Oliyai R., Oh D., Järvinen T., and Savolainen J. Prodrugs: design and clinical applications. Nat Rev Drug Discov 7 (2008) 255-270. A well-organized, well-written, and information-rich review on the design of prodrugs and their clinical objectives.
    • (2008) Nat Rev Drug Discov , vol.7 , pp. 255-270
    • Raito, J.1    Kumpulainen, H.2    Heimbach, T.3    Oliyai, R.4    Oh, D.5    Järvinen, T.6    Savolainen, J.7
  • 3
    • 67649879923 scopus 로고    scopus 로고
    • Designing prodrugs and bioprecursors
    • Wermuth C.G. (Ed), Elsevier, Amsterdam
    • Wermuth C.G. Designing prodrugs and bioprecursors. In: Wermuth C.G. (Ed). The Practice of Medicinal Chemistry. edn 3 (2008), Elsevier, Amsterdam 721-746
    • (2008) The Practice of Medicinal Chemistry. edn 3 , pp. 721-746
    • Wermuth, C.G.1
  • 5
    • 84906476318 scopus 로고    scopus 로고
    • Testa B: Prodrug objectives and design. In ADME-Tox Approaches. Edited by Testa B, van de Waterbeemd H. 5 in Comprehensive Medicinal Chemistry II. Edited by Taylor JB, Triggle DJ. Oxford, UK: Elsevier; 2007:1009-1041.
    • Testa B: Prodrug objectives and design. In ADME-Tox Approaches. Edited by Testa B, van de Waterbeemd H. Volume 5 in Comprehensive Medicinal Chemistry II. Edited by Taylor JB, Triggle DJ. Oxford, UK: Elsevier; 2007:1009-1041.
  • 6
    • 34548026715 scopus 로고    scopus 로고
    • Stella V.J., Borchardt R.T., Hageman M.J., Oliyai R., Maag H., and Tilley J.W. (Eds), Springer, New York
    • In: Stella V.J., Borchardt R.T., Hageman M.J., Oliyai R., Maag H., and Tilley J.W. (Eds). Prodrugs: Challenges and Rewards. Parts 1 and 2 (2007), Springer, New York
    • (2007) Prodrugs: Challenges and Rewards. Parts 1 and 2
  • 8
    • 7444253306 scopus 로고    scopus 로고
    • Prodrug research: futile or fertile?
    • Testa B. Prodrug research: futile or fertile?. Biochem Pharmacol 68 (2004) 2097-2106
    • (2004) Biochem Pharmacol , vol.68 , pp. 2097-2106
    • Testa, B.1
  • 9
    • 2342481809 scopus 로고    scopus 로고
    • Lessons learned from marketed and investigational prodrugs
    • Ettmayer P., Amidon G., Clement B., and Testa B. Lessons learned from marketed and investigational prodrugs. J Med Chem 47 (2004) 2393-2404
    • (2004) J Med Chem , vol.47 , pp. 2393-2404
    • Ettmayer, P.1    Amidon, G.2    Clement, B.3    Testa, B.4
  • 10
    • 19444364011 scopus 로고    scopus 로고
    • Prodrug strategies in the design of nucleoside and nucleotide antiviral therapeutics
    • Mackman R.L., and Cihlar T. Prodrug strategies in the design of nucleoside and nucleotide antiviral therapeutics. Annu Rep Med Chem 39 (2004) 305-321
    • (2004) Annu Rep Med Chem , vol.39 , pp. 305-321
    • Mackman, R.L.1    Cihlar, T.2
  • 12
    • 0346958512 scopus 로고    scopus 로고
    • Design of ester prodrugs to enhance oral absorption of poorly permeable compounds: challenges to the discovery scientist
    • Beaumont K., Webster R., Gardner I., and Dack K. Design of ester prodrugs to enhance oral absorption of poorly permeable compounds: challenges to the discovery scientist. Curr Drug Metab 4 (2003) 461-485
    • (2003) Curr Drug Metab , vol.4 , pp. 461-485
    • Beaumont, K.1    Webster, R.2    Gardner, I.3    Dack, K.4
  • 13
    • 0033006069 scopus 로고    scopus 로고
    • Prodrug approaches in the improved delivery of peptide drugs
    • Wang W., Jiang J., Ballard C.E., and Wang B. Prodrug approaches in the improved delivery of peptide drugs. Curr Pharm Des 5 (1999) 265-287
    • (1999) Curr Pharm Des , vol.5 , pp. 265-287
    • Wang, W.1    Jiang, J.2    Ballard, C.E.3    Wang, B.4
  • 15
    • 0343724706 scopus 로고    scopus 로고
    • Prodrugs for improved CNS delivery
    • Bradley D.A. Prodrugs for improved CNS delivery. Adv Drug Deliv Rev 19 (1996) 171-202
    • (1996) Adv Drug Deliv Rev , vol.19 , pp. 171-202
    • Bradley, D.A.1
  • 16
    • 0001199533 scopus 로고
    • Chemical aspects of selective toxicity
    • Albert A. Chemical aspects of selective toxicity. Nature 182 (1958) 421-422
    • (1958) Nature , vol.182 , pp. 421-422
    • Albert, A.1
  • 17
    • 0041919716 scopus 로고    scopus 로고
    • A novel approach of water-soluble paclitaxel prodrug with no auxiliary and no byproduct: Design and synthesis of isotaxel
    • Hayashi Y., Skwarczynski M., Hamada Y., Sohma Y., Kimura T., and Kiso Y. A novel approach of water-soluble paclitaxel prodrug with no auxiliary and no byproduct: Design and synthesis of isotaxel. J Med Chem 47 (2004) 3782-3784
    • (2004) J Med Chem , vol.47 , pp. 3782-3784
    • Hayashi, Y.1    Skwarczynski, M.2    Hamada, Y.3    Sohma, Y.4    Kimura, T.5    Kiso, Y.6
  • 18
    • 17144381272 scopus 로고    scopus 로고
    • No auxiliary, no byproduct strategy for water-soluble prodrugs of taxoids: scope and limitation of O-N intramolecular acyl and acyloxy migration reactions
    • Skwarczynski M., Sohma Y., Noguchi M., Kimura M., Hayashi Y., Hamada Y., Kimura T., and Kiso Y. No auxiliary, no byproduct strategy for water-soluble prodrugs of taxoids: scope and limitation of O-N intramolecular acyl and acyloxy migration reactions. J Med Chem 48 (2005) 2655-2666
    • (2005) J Med Chem , vol.48 , pp. 2655-2666
    • Skwarczynski, M.1    Sohma, Y.2    Noguchi, M.3    Kimura, M.4    Hayashi, Y.5    Hamada, Y.6    Kimura, T.7    Kiso, Y.8
  • 19
    • 0028948839 scopus 로고
    • A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability
    • Amidon G.L., Lennernäs H., Shah V.P., and Crison J.R. A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm Res 12 (1995) 413-420
    • (1995) Pharm Res , vol.12 , pp. 413-420
    • Amidon, G.L.1    Lennernäs, H.2    Shah, V.P.3    Crison, J.R.4
  • 25
    • 0038508970 scopus 로고    scopus 로고
    • The metabolism of clopidogrel is catalyzed by human cytochrome P450 3A and is inhibited by atorvastin
    • Clarke T.A., and Waskell L.A. The metabolism of clopidogrel is catalyzed by human cytochrome P450 3A and is inhibited by atorvastin. Drug Metab Dispos 31 (2003) 53-59
    • (2003) Drug Metab Dispos , vol.31 , pp. 53-59
    • Clarke, T.A.1    Waskell, L.A.2
  • 26
    • 62249112083 scopus 로고    scopus 로고
    • Metabolic oxidative cleavage of thioesters: evidence for the formation of sulfenic acid intermediates in the bioactivation of the antithrombotic prodrugs ticlopidine and clopidogrel
    • A remarkable research paper revealing new and significant details on the enzymatic mechanism of activation of antiaggregating prodrugs.
    • Dansette P.M., Libraire J., Bertho G., and Mansuy D. Metabolic oxidative cleavage of thioesters: evidence for the formation of sulfenic acid intermediates in the bioactivation of the antithrombotic prodrugs ticlopidine and clopidogrel. Chem Res Toxicol 22 (2009) 369-373. A remarkable research paper revealing new and significant details on the enzymatic mechanism of activation of antiaggregating prodrugs.
    • (2009) Chem Res Toxicol , vol.22 , pp. 369-373
    • Dansette, P.M.1    Libraire, J.2    Bertho, G.3    Mansuy, D.4
  • 30
    • 61449105900 scopus 로고    scopus 로고
    • Synthesis, reduction potentials, and antitubercular activity of ring A/B analogues of the bioreductive drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824)
    • While nitro aromatic compounds are known since decades as antibacterial and antiparasitic bioprecursors, this study generates new hopes by applying the concept to the fight against tuberculosis.
    • Thompson A.M., Blaser A., Anderson R.F., Shinde S.S., Franzblau S.G., Ma Z., Denny W.A., and Palmer B.D. Synthesis, reduction potentials, and antitubercular activity of ring A/B analogues of the bioreductive drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824). J Med Chem 52 (2009) 637-645. While nitro aromatic compounds are known since decades as antibacterial and antiparasitic bioprecursors, this study generates new hopes by applying the concept to the fight against tuberculosis.
    • (2009) J Med Chem , vol.52 , pp. 637-645
    • Thompson, A.M.1    Blaser, A.2    Anderson, R.F.3    Shinde, S.S.4    Franzblau, S.G.5    Ma, Z.6    Denny, W.A.7    Palmer, B.D.8
  • 31
    • 33847092271 scopus 로고    scopus 로고
    • The biochemistry of drug metabolism - an introduction. Part 2. Redox reactions and their enzymes
    • Testa B., and Krämer S.D. The biochemistry of drug metabolism - an introduction. Part 2. Redox reactions and their enzymes. Chem Biodivers 4 (2007) 257-405
    • (2007) Chem Biodivers , vol.4 , pp. 257-405
    • Testa, B.1    Krämer, S.D.2
  • 32
    • 0037460188 scopus 로고    scopus 로고
    • Activation of 3-amino-1,2,4-benzotriazine 1,4-dioxide antitumor agents to oxidizing species following their one-electron reduction
    • Anderson R.F., Shinde S.S., Hay M.P., Gamage S.A., and Denny W.A. Activation of 3-amino-1,2,4-benzotriazine 1,4-dioxide antitumor agents to oxidizing species following their one-electron reduction. J Am Chem Soc 125 (2003) 748-756
    • (2003) J Am Chem Soc , vol.125 , pp. 748-756
    • Anderson, R.F.1    Shinde, S.S.2    Hay, M.P.3    Gamage, S.A.4    Denny, W.A.5
  • 33
    • 37349056730 scopus 로고    scopus 로고
    • Hypoxia-selective 3-alkyl 1,2,4-benzotriazine 1,4-dioxides: the influence of hydrogen bond donors on extravascular transport and antitumor activity
    • Hay M.P., Pchalek K., Pruijn F.B., Hicks K.O., Siim B.G., Anderson R.F., Shinde S.S., Phillips V., Denny W.A., and Wilson W.R. Hypoxia-selective 3-alkyl 1,2,4-benzotriazine 1,4-dioxides: the influence of hydrogen bond donors on extravascular transport and antitumor activity. J Med Chem 50 (2007) 6654-6664
    • (2007) J Med Chem , vol.50 , pp. 6654-6664
    • Hay, M.P.1    Pchalek, K.2    Pruijn, F.B.3    Hicks, K.O.4    Siim, B.G.5    Anderson, R.F.6    Shinde, S.S.7    Phillips, V.8    Denny, W.A.9    Wilson, W.R.10
  • 34
    • 35848964831 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of new 2-arylcarbonyl-3-trifluoromethylquinoxaline 1,4-di-N-oxide derivatives and their reduced analogues
    • Solano B., Junnotula V., Marin A., Villar R., Burguete A., Vicente E., Perez-Silanes S., Aldana I., Monge A., Dutta S., et al. Synthesis and biological evaluation of new 2-arylcarbonyl-3-trifluoromethylquinoxaline 1,4-di-N-oxide derivatives and their reduced analogues. J Med Chem 50 (2007) 5485-5492
    • (2007) J Med Chem , vol.50 , pp. 5485-5492
    • Solano, B.1    Junnotula, V.2    Marin, A.3    Villar, R.4    Burguete, A.5    Vicente, E.6    Perez-Silanes, S.7    Aldana, I.8    Monge, A.9    Dutta, S.10
  • 35
    • 58849153727 scopus 로고    scopus 로고
    • Design of anticancer prodrugs for reductive activation
    • Chen Y., and Hu L. Design of anticancer prodrugs for reductive activation. Med Res Rev 29 (2009) 29-64
    • (2009) Med Res Rev , vol.29 , pp. 29-64
    • Chen, Y.1    Hu, L.2
  • 36
    • 21244461192 scopus 로고    scopus 로고
    • Hypoxia-activated anticancer drugs
    • Denny W.A. Hypoxia-activated anticancer drugs. Expert Opin Ther Patents 15 (2005) 635-646
    • (2005) Expert Opin Ther Patents , vol.15 , pp. 635-646
    • Denny, W.A.1
  • 37
    • 34547653834 scopus 로고    scopus 로고
    • Identification of human reductases that activate the dinitrobenzamide mustard prodrug PR-104A: a role for NADPH-cytochrome P450 oxidoreductase under hypoxia
    • Guise C.P., Wang A.T., Theil A., Bridewell D.J., Wilson W.R., and Patterson A.V. Identification of human reductases that activate the dinitrobenzamide mustard prodrug PR-104A: a role for NADPH-cytochrome P450 oxidoreductase under hypoxia. Biochem Pharmacol 74 (2007) 810-820
    • (2007) Biochem Pharmacol , vol.74 , pp. 810-820
    • Guise, C.P.1    Wang, A.T.2    Theil, A.3    Bridewell, D.J.4    Wilson, W.R.5    Patterson, A.V.6
  • 39
    • 34249037167 scopus 로고    scopus 로고
    • Pharmacokinetics and metabolism of the prodrug DB289 (2,5-bis[4-(N-methoxyamidino)phenyl]furan monomaleate) in rats and monkey and its conversion to the antiprotozoal/antifungal drug DB75 (2,5-bis(4-guanylphenyl)furan dihydrochloride)
    • Midgley I., Fitzpatrick K., Taylor L.M., Houchen T.L., Henderson S.J., Wright S.J., Cybulski Z.R., John B.A., McBurney A., Boykin D.W., et al. Pharmacokinetics and metabolism of the prodrug DB289 (2,5-bis[4-(N-methoxyamidino)phenyl]furan monomaleate) in rats and monkey and its conversion to the antiprotozoal/antifungal drug DB75 (2,5-bis(4-guanylphenyl)furan dihydrochloride). Drug Metab Dispos 35 (2007) 955-967
    • (2007) Drug Metab Dispos , vol.35 , pp. 955-967
    • Midgley, I.1    Fitzpatrick, K.2    Taylor, L.M.3    Houchen, T.L.4    Henderson, S.J.5    Wright, S.J.6    Cybulski, Z.R.7    John, B.A.8    McBurney, A.9    Boykin, D.W.10
  • 40
    • 34547584200 scopus 로고    scopus 로고
    • Basis for design and development of platinum(IV) anticancer complexes
    • Hall M.D., Mellor H.R., Callaghan R., and Hambley T.W. Basis for design and development of platinum(IV) anticancer complexes. J Med Chem 50 (2007) 3403-3411
    • (2007) J Med Chem , vol.50 , pp. 3403-3411
    • Hall, M.D.1    Mellor, H.R.2    Callaghan, R.3    Hambley, T.W.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.