-
1
-
-
67649392788
-
-
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
-
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
-
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
-
4
-
-
85017417458
-
Prodrugs
-
van de Waterbeemd H., and Testa B. (Eds), Wiley-VCH, Weinheim
-
Testa B. Prodrugs. In: van de Waterbeemd H., and Testa B. (Eds). Drug Bioavailability - Estimation of Solubility, Permeability, Absorption and Bioavailability. edn 2 (2008), Wiley-VCH, Weinheim 559-570
-
(2008)
Drug Bioavailability - Estimation of Solubility, Permeability, Absorption and Bioavailability. edn 2
, pp. 559-570
-
-
Testa, B.1
-
5
-
-
84906476318
-
-
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
-
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
21
-
-
39149114424
-
Pradefovir: a prodrug that targets adefovir to the liver for the treatment of hepatitis B
-
Reddy K.R., Matelich M.C., Ugarkar B.G., Gómez-Galeno J.E., DaRe J., Ollis K., Sun Z., Craigo W., Colby T.J., Fujitaki J.M., et al. Pradefovir: a prodrug that targets adefovir to the liver for the treatment of hepatitis B. J Med Chem 51 (2008) 666-676
-
(2008)
J Med Chem
, vol.51
, pp. 666-676
-
-
Reddy, K.R.1
Matelich, M.C.2
Ugarkar, B.G.3
Gómez-Galeno, J.E.4
DaRe, J.5
Ollis, K.6
Sun, Z.7
Craigo, W.8
Colby, T.J.9
Fujitaki, J.M.10
-
24
-
-
18644372477
-
Structure and stereochemistry of the active metabolite of clopidogrel
-
Pereillo J.M., Maftouh M., Andrieu A., Uzabiaga M.F., Fedeli O., Savi P., Pascal M., Herbert J.M., Maffrand J.P., and Picard C. Structure and stereochemistry of the active metabolite of clopidogrel. Drug Metab Dispos 30 (2002) 1288-1295
-
(2002)
Drug Metab Dispos
, vol.30
, pp. 1288-1295
-
-
Pereillo, J.M.1
Maftouh, M.2
Andrieu, A.3
Uzabiaga, M.F.4
Fedeli, O.5
Savi, P.6
Pascal, M.7
Herbert, J.M.8
Maffrand, J.P.9
Picard, C.10
-
25
-
-
0038508970
-
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
-
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
-
27
-
-
34249053105
-
The disposition of prasugrel, a novel thienopyridine, in humans
-
Farid N.A., Smith R.L., Gillespie T.A., Rash T.J., Blair P.E., Kurihara A., and Goldberg M.J. The disposition of prasugrel, a novel thienopyridine, in humans. Drug Metab Dispos 35 (2007) 1096-1104
-
(2007)
Drug Metab Dispos
, vol.35
, pp. 1096-1104
-
-
Farid, N.A.1
Smith, R.L.2
Gillespie, T.A.3
Rash, T.J.4
Blair, P.E.5
Kurihara, A.6
Goldberg, M.J.7
-
28
-
-
46449103184
-
The biotransformation of prasugrel, a new thienopyridine prodrug, by the human carboxylesterases 1 and 2
-
Williams E.T., Jones K.O., Ponsler G.D., Lowery S.M., Perkins E.J., Wrighton S.A., Ruterbories K.J., Kazui M., and Farid N.A. The biotransformation of prasugrel, a new thienopyridine prodrug, by the human carboxylesterases 1 and 2. Drug Metab Dispos 36 (2008) 1227-1232
-
(2008)
Drug Metab Dispos
, vol.36
, pp. 1227-1232
-
-
Williams, E.T.1
Jones, K.O.2
Ponsler, G.D.3
Lowery, S.M.4
Perkins, E.J.5
Wrighton, S.A.6
Ruterbories, K.J.7
Kazui, M.8
Farid, N.A.9
-
30
-
-
61449105900
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
38
-
-
33845433862
-
Novel pathways associated with quinone-induced stress in breast cancer cells
-
Benz C.C., Atsriku C., Yau C., Britton D., Schilling B., Gibson B.W., Baldwin M.A., and Scott G.K. Novel pathways associated with quinone-induced stress in breast cancer cells. Drug Metab Rev 38 (2006) 601-613
-
(2006)
Drug Metab Rev
, vol.38
, pp. 601-613
-
-
Benz, C.C.1
Atsriku, C.2
Yau, C.3
Britton, D.4
Schilling, B.5
Gibson, B.W.6
Baldwin, M.A.7
Scott, G.K.8
-
39
-
-
34249037167
-
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
-
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
|