메뉴 건너뛰기




Volumn 9, Issue 2, 2014, Pages 65-74

Current prodrug strategies for improving oral absorption of nucleoside analogues

Author keywords

Nucleoside analogues; Oral bioavailability; Prodrug

Indexed keywords

2' DEOXY 2' FLUORO 2' METHYLCYTIDINE; 3 [4 HYDROXY 5 (HYDROXYMETHYL)TETRAHYDROFURAN 2 YL] 6 (4 PENTYLPHENYL)FURO[2,3 D]PYRIMIDIN 2 ONE; 5' O LEVO VALYLESTER; ABACAVIR; ABACAVIR PHOSPHORAMIDATE; ACICLOVIR; ADEFOVIR; ADEFOVIR DIPIVOXIL; CARBOVIR; CIDOFOVIR; DIDANOSINE; DIPEPTIDYL PEPTIDASE IV; ESTER; FAMCICLOVIR; GANCICLOVIR; GEMCITABINE; LAGOCICLOVIR; MERICITABINE; NUCLEOSIDE ANALOG; PENCICLOVIR; PRODRUG; RIBAVIRIN; TARIBAVIRIN; TENOFOVIR DISOPROXIL; TETRAPEPTIDE AMIDE; TRIPEPTIDE ESTER; UNCLASSIFIED DRUG; VALACICLOVIR; VALGANCICLOVIR; VALYLOXYPROPYLESTER; VILDAGLIPTIN;

EID: 84919785501     PISSN: 18180876     EISSN: 2221285X     Source Type: Journal    
DOI: 10.1016/j.ajps.2013.12.006     Document Type: Review
Times cited : (41)

References (91)
  • 1
    • 0032846316 scopus 로고    scopus 로고
    • Involvement of multiple transporters in the oral absorption of nucleoside analogues
    • Balimane P.V., Sinko P.J. Involvement of multiple transporters in the oral absorption of nucleoside analogues. Adv Drug Deliv Rev 1999, 39:183-209.
    • (1999) Adv Drug Deliv Rev , vol.39 , pp. 183-209
    • Balimane, P.V.1    Sinko, P.J.2
  • 2
    • 65649111235 scopus 로고    scopus 로고
    • Strategies to increase the oral bioavailability of nucleoside analogs
    • Lalanne M., Andrieux K., Couvreur P. Strategies to increase the oral bioavailability of nucleoside analogs. Curr Med Chem 2009, 16:1391-1399.
    • (2009) Curr Med Chem , vol.16 , pp. 1391-1399
    • Lalanne, M.1    Andrieux, K.2    Couvreur, P.3
  • 3
    • 2342531101 scopus 로고    scopus 로고
    • Antiviral drugs in current clinical use
    • De Clercq E. Antiviral drugs in current clinical use. J Clin Virol 2004, 30:115-133.
    • (2004) J Clin Virol , vol.30 , pp. 115-133
    • De Clercq, E.1
  • 5
    • 42949174825 scopus 로고    scopus 로고
    • Prodrugs of nucleoside analogues for improved oral absorption and tissue targeting
    • Li F.J., Maag H., Alfredson T. Prodrugs of nucleoside analogues for improved oral absorption and tissue targeting. J Pharm Sci 2008, 97:1109-1134.
    • (2008) J Pharm Sci , vol.97 , pp. 1109-1134
    • Li, F.J.1    Maag, H.2    Alfredson, T.3
  • 6
    • 0036137373 scopus 로고    scopus 로고
    • High dose oral ganciclovir treatment for cytomegalovirus retinitis
    • Lalezari J.P., Friedberg D.N., Bissett J., et al. High dose oral ganciclovir treatment for cytomegalovirus retinitis. J Clin Virol 2002, 24:67-77.
    • (2002) J Clin Virol , vol.24 , pp. 67-77
    • Lalezari, J.P.1    Friedberg, D.N.2    Bissett, J.3
  • 7
    • 0032997095 scopus 로고    scopus 로고
    • Clinical pharmacokinetics of the antiviral nucleotide analogues cidofovir and adefovir
    • Cundy K.C. Clinical pharmacokinetics of the antiviral nucleotide analogues cidofovir and adefovir. Clin Pharmacokinet 1999, 36:127-143.
    • (1999) Clin Pharmacokinet , vol.36 , pp. 127-143
    • Cundy, K.C.1
  • 8
    • 0023898828 scopus 로고
    • Pyrimidine dideoxyribonucleosides: selectivity of penetration into cerebrospinal fluid
    • Collins J.M., Klecker R.W., Kelley J.A., et al. Pyrimidine dideoxyribonucleosides: selectivity of penetration into cerebrospinal fluid. J Pharmacol Exp Ther 1988, 245:466-470.
    • (1988) J Pharmacol Exp Ther , vol.245 , pp. 466-470
    • Collins, J.M.1    Klecker, R.W.2    Kelley, J.A.3
  • 9
    • 0025141473 scopus 로고
    • A pilot study of the bioavailability and pharmacokinetics of 2',3'-dideoxycytidine in patients with AIDS or AIDS-related complex
    • Gustavson L.E., Fukuda E.K., Rubio F.A., et al. A pilot study of the bioavailability and pharmacokinetics of 2',3'-dideoxycytidine in patients with AIDS or AIDS-related complex. J Acquir Immune Defic Syndr 1990, 3:28-31.
    • (1990) J Acquir Immune Defic Syndr , vol.3 , pp. 28-31
    • Gustavson, L.E.1    Fukuda, E.K.2    Rubio, F.A.3
  • 10
    • 0023091771 scopus 로고
    • Plasma and cerebrospinal fluid pharmacokinetics of 3'-azido-3'-deoxythymidine: a novel pyrimidine analog with potential application for the treatment of patients with AIDS and related diseases
    • Klecker R.W., Collins J.M., Yarchoan R., et al. Plasma and cerebrospinal fluid pharmacokinetics of 3'-azido-3'-deoxythymidine: a novel pyrimidine analog with potential application for the treatment of patients with AIDS and related diseases. Clin Pharmacol Ther 1987, 41:407-412.
    • (1987) Clin Pharmacol Ther , vol.41 , pp. 407-412
    • Klecker, R.W.1    Collins, J.M.2    Yarchoan, R.3
  • 11
    • 0025763660 scopus 로고
    • Pharmacokinetics of didanosine in patients with acquired immunodeficiency syndrome or acquired immunodeficiency syndrome-related complex
    • Knupp C.A., Shyu W.C., Dolin R., et al. Pharmacokinetics of didanosine in patients with acquired immunodeficiency syndrome or acquired immunodeficiency syndrome-related complex. Clin Pharmacol Ther 1991, 49:523-535.
    • (1991) Clin Pharmacol Ther , vol.49 , pp. 523-535
    • Knupp, C.A.1    Shyu, W.C.2    Dolin, R.3
  • 12
    • 0023266214 scopus 로고
    • The toxicity of azidothymidine (AZT) in the treatment of patients with AIDS and AIDS-related complex. A double-blind, placebo-controlled trial
    • Richman D.D., Fischl M.A., Grieco M.H., et al. The toxicity of azidothymidine (AZT) in the treatment of patients with AIDS and AIDS-related complex. A double-blind, placebo-controlled trial. N Engl J Med 1987, 317:192-197.
    • (1987) N Engl J Med , vol.317 , pp. 192-197
    • Richman, D.D.1    Fischl, M.A.2    Grieco, M.H.3
  • 13
    • 17644446926 scopus 로고
    • The National Cancer Institute phase I study of 2',3'-dideoxyinosine administration in adults with AIDS or AIDS-related complex: analysis of activity and toxicity profiles
    • Yarchoan R., Mitsuya H.J., Pluda M., et al. The National Cancer Institute phase I study of 2',3'-dideoxyinosine administration in adults with AIDS or AIDS-related complex: analysis of activity and toxicity profiles. Rev Infect Dis 1990, 12:522-533.
    • (1990) Rev Infect Dis , vol.12 , pp. 522-533
    • Yarchoan, R.1    Mitsuya, H.J.2    Pluda, M.3
  • 14
    • 0027768955 scopus 로고
    • Pharmacokinetics of the acyclovir prodrug valaciclovir after escalating single- and multiple-dose administration to normal volunte
    • Weller S., Blum M.R., Doucette M., et al. Pharmacokinetics of the acyclovir prodrug valaciclovir after escalating single- and multiple-dose administration to normal volunte. Clin Pharmacol Ther 1993, 54:595-605.
    • (1993) Clin Pharmacol Ther , vol.54 , pp. 595-605
    • Weller, S.1    Blum, M.R.2    Doucette, M.3
  • 15
    • 0033621571 scopus 로고    scopus 로고
    • Bioavailability of aciclovir after oral administration of aciclovir and its prodrug valaciclovir to patients with leukopenia after chemotherapy
    • Steingrimsdottir H., Gruber A., Palm C., et al. Bioavailability of aciclovir after oral administration of aciclovir and its prodrug valaciclovir to patients with leukopenia after chemotherapy. Antimicrob Agents Chemother 2000, 44:207-209.
    • (2000) Antimicrob Agents Chemother , vol.44 , pp. 207-209
    • Steingrimsdottir, H.1    Gruber, A.2    Palm, C.3
  • 16
    • 0032158915 scopus 로고    scopus 로고
    • Transport of l-valine-acyclovir via the oligopeptide transporter in the human intestinal cell line, Caco-2
    • De Vrueh R.L.A., Smith P.L., Lee C.P. Transport of l-valine-acyclovir via the oligopeptide transporter in the human intestinal cell line, Caco-2. J Pharmacol Exp Ther 1998, 286:1166-1170.
    • (1998) J Pharmacol Exp Ther , vol.286 , pp. 1166-1170
    • De Vrueh, R.L.A.1    Smith, P.L.2    Lee, C.P.3
  • 17
    • 0032544684 scopus 로고    scopus 로고
    • Direct evidence for peptide transporter (PepT1)-mediated uptake of a nonpeptide prodrug, valacyclovir
    • Balimane P.V., Tamai I., Guo a, et al. Direct evidence for peptide transporter (PepT1)-mediated uptake of a nonpeptide prodrug, valacyclovir. Biochem Biophys Res Commun 1998, 250:246-251.
    • (1998) Biochem Biophys Res Commun , vol.250 , pp. 246-251
    • Balimane, P.V.1    Tamai, I.2    Guo, A.3
  • 18
    • 0037815496 scopus 로고    scopus 로고
    • Identification of a human valacyclovirase: biphenyl hydrolase-like protein as valacyclovir hydrolase
    • Kim I., Chu X.-Y., Kim S., et al. Identification of a human valacyclovirase: biphenyl hydrolase-like protein as valacyclovir hydrolase. J Biol Chem 2003, 278:25348-25356.
    • (2003) J Biol Chem , vol.278 , pp. 25348-25356
    • Kim, I.1    Chu, X.-Y.2    Kim, S.3
  • 19
    • 0029045258 scopus 로고
    • Cloning and expression analysis of a novel human serine hydrolase with sequence similarity to prokaryotic enzymes involved in the degradation of aromatic compounds
    • Puente X.S., López-Otn C. Cloning and expression analysis of a novel human serine hydrolase with sequence similarity to prokaryotic enzymes involved in the degradation of aromatic compounds. J Biol Chem 1995, 270:12926-12932.
    • (1995) J Biol Chem , vol.270 , pp. 12926-12932
    • Puente, X.S.1    López-Otn, C.2
  • 20
    • 0024505073 scopus 로고
    • Use of the peptide carrier system to improve the intestinal absorption of l-α-methyldopa: carrier kinetics, intestinal permeabilities, and invitro hydrolysis of dipeptidyl derivatives of l-α-methyldopa
    • Hu M., Subramanian P., Mosberg H.I., et al. Use of the peptide carrier system to improve the intestinal absorption of l-α-methyldopa: carrier kinetics, intestinal permeabilities, and invitro hydrolysis of dipeptidyl derivatives of l-α-methyldopa. Pharm Res 1989, 6:66-70.
    • (1989) Pharm Res , vol.6 , pp. 66-70
    • Hu, M.1    Subramanian, P.2    Mosberg, H.I.3
  • 21
    • 0038017245 scopus 로고    scopus 로고
    • Synthesis and characterization of novel dipeptide ester prodrugs of acyclovir
    • Nashed Y. Synthesis and characterization of novel dipeptide ester prodrugs of acyclovir. Spectrochim Acta A 2003, 59:2033-2039.
    • (2003) Spectrochim Acta A , vol.59 , pp. 2033-2039
    • Nashed, Y.1
  • 22
    • 0037308045 scopus 로고    scopus 로고
    • Interactions of the dipeptide ester prodrugs of acyclovir with the intestinal oligopeptide transporter: competitive inhibition of glycylsarcosine transport in human intestinal cell
    • Anand B.S., Patel J., Mitra A.K. Interactions of the dipeptide ester prodrugs of acyclovir with the intestinal oligopeptide transporter: competitive inhibition of glycylsarcosine transport in human intestinal cell. Pharmacology 2003, 304:781-791.
    • (2003) Pharmacology , vol.304 , pp. 781-791
    • Anand, B.S.1    Patel, J.2    Mitra, A.K.3
  • 23
    • 6344288793 scopus 로고    scopus 로고
    • Pharmacokinetics of novel dipeptide ester prodrugs of acyclovir after oral administration: intestinal absorption and liver metabolism
    • Anand B.S., Katragadda S., Mitra A.K. Pharmacokinetics of novel dipeptide ester prodrugs of acyclovir after oral administration: intestinal absorption and liver metabolism. Pharmacology 2004, 311:659-667.
    • (2004) Pharmacology , vol.311 , pp. 659-667
    • Anand, B.S.1    Katragadda, S.2    Mitra, A.K.3
  • 24
    • 0021287132 scopus 로고
    • Ta1, a novel 105 kDa human T cell activation antigen defined by a monoclonal antibody
    • Fox D.A., Hussey R.E., Fitzgerald K.A., et al. Ta1, a novel 105 kDa human T cell activation antigen defined by a monoclonal antibody. J Immunol 1984, 133:1250-1256.
    • (1984) J Immunol , vol.133 , pp. 1250-1256
    • Fox, D.A.1    Hussey, R.E.2    Fitzgerald, K.A.3
  • 25
    • 0033619675 scopus 로고    scopus 로고
    • Dipeptidyl-peptidase IV (CD26)-role in the inactivation of regulatory peptides
    • Mentlein R. Dipeptidyl-peptidase IV (CD26)-role in the inactivation of regulatory peptides. Regul Pept 1999, 85:9-24.
    • (1999) Regul Pept , vol.85 , pp. 9-24
    • Mentlein, R.1
  • 26
    • 3042833899 scopus 로고    scopus 로고
    • Cell-surface peptidases
    • Mentlein R. Cell-surface peptidases. Int Rev Cytol 2004, 235:165-202.
    • (2004) Int Rev Cytol , vol.235 , pp. 165-202
    • Mentlein, R.1
  • 27
    • 84886740089 scopus 로고    scopus 로고
    • Novel water-soluble prodrugs of acyclovir cleavable by the dipeptidylpeptidase IV (DPP IV/CD26) enzyme
    • Diez-Torrubia A., Cabrera S., Castro S., et al. Novel water-soluble prodrugs of acyclovir cleavable by the dipeptidylpeptidase IV (DPP IV/CD26) enzyme. Eur J Med Chem 2013, 70:456-468.
    • (2013) Eur J Med Chem , vol.70 , pp. 456-468
    • Diez-Torrubia, A.1    Cabrera, S.2    Castro, S.3
  • 28
    • 33747141729 scopus 로고    scopus 로고
    • Antiviral drugs for cytomegalovirus diseases
    • Biron K.K. Antiviral drugs for cytomegalovirus diseases. Antivir Res 2006, 71:154-163.
    • (2006) Antivir Res , vol.71 , pp. 154-163
    • Biron, K.K.1
  • 29
    • 0033812228 scopus 로고    scopus 로고
    • Transport of valganciclovir, a ganciclovir prodrug, via peptide transporters PEPT1 and PEPT2
    • Leibach F.H., Ganapathy V., Ganapathy M.E. Transport of valganciclovir, a ganciclovir prodrug, via peptide transporters PEPT1 and PEPT2. J Pharm Sci 2000, 89:781-789.
    • (2000) J Pharm Sci , vol.89 , pp. 781-789
    • Leibach, F.H.1    Ganapathy, V.2    Ganapathy, M.E.3
  • 30
    • 17944368059 scopus 로고    scopus 로고
    • Valganciclovir: a review of its use in the management of CMV infection and disease in immunocompromised patients
    • Cvetkovic R.S., Wellington K. Valganciclovir: a review of its use in the management of CMV infection and disease in immunocompromised patients. Drugs 2005, 65:859-878.
    • (2005) Drugs , vol.65 , pp. 859-878
    • Cvetkovic, R.S.1    Wellington, K.2
  • 31
    • 0033370077 scopus 로고    scopus 로고
    • Didanosine - an updated review of its use in HIV infection
    • Perry C.M., Nobel S. Didanosine - an updated review of its use in HIV infection. Drugs 1999, 58:1099-1135.
    • (1999) Drugs , vol.58 , pp. 1099-1135
    • Perry, C.M.1    Nobel, S.2
  • 32
    • 0031957736 scopus 로고    scopus 로고
    • Absorption and intestinal metabolism of purine dideoxynucleosides and an adenosine deaminaseactivated prodrug of 20,3-dideoxyinosine in the mesenteric vein cannulated rat ileum
    • Singhal D., Ho N.F., Anderson B.D. Absorption and intestinal metabolism of purine dideoxynucleosides and an adenosine deaminaseactivated prodrug of 20,3-dideoxyinosine in the mesenteric vein cannulated rat ileum. J Pharm Sci 1998, 87:569-577.
    • (1998) J Pharm Sci , vol.87 , pp. 569-577
    • Singhal, D.1    Ho, N.F.2    Anderson, B.D.3
  • 33
    • 0029151512 scopus 로고
    • Enhanced oral bioavailability of DDI after administration of 6-Cl-ddP, an adenosine deaminase-activated prodrug, to chronically catheterized rats
    • Anderson B.D., Morgan M.E., Singhal D. Enhanced oral bioavailability of DDI after administration of 6-Cl-ddP, an adenosine deaminase-activated prodrug, to chronically catheterized rats. Pharm Res 1995, 12:1126-1133.
    • (1995) Pharm Res , vol.12 , pp. 1126-1133
    • Anderson, B.D.1    Morgan, M.E.2    Singhal, D.3
  • 34
    • 33847719015 scopus 로고    scopus 로고
    • Synthesis and invitro anti-HIV activities of didanosine prodrugs
    • Sriram D., Yogeeswari P., Babu N.R., et al. Synthesis and invitro anti-HIV activities of didanosine prodrugs. J Enzyme Inhib Med Chem 2007, 22:51-55.
    • (2007) J Enzyme Inhib Med Chem , vol.22 , pp. 51-55
    • Sriram, D.1    Yogeeswari, P.2    Babu, N.R.3
  • 35
    • 79953825653 scopus 로고    scopus 로고
    • Bifunctional peptidomimetic prodrugs of didanosine for improved intestinal permeability and enhanced acidic stability: synthesis, transepithelial transport, chemical stability and pharmacokinetics
    • Yan Z.T., Sun J., Chang Y.N., et al. Bifunctional peptidomimetic prodrugs of didanosine for improved intestinal permeability and enhanced acidic stability: synthesis, transepithelial transport, chemical stability and pharmacokinetics. Mol Pharm 2011, 8:319-329.
    • (2011) Mol Pharm , vol.8 , pp. 319-329
    • Yan, Z.T.1    Sun, J.2    Chang, Y.N.3
  • 36
    • 0023633215 scopus 로고
    • Antiherpesvirus activity of 9-(4-hydroxy-3-hydroxy-methylbut-1-yl)guanine (BRL 39123) in cell culture
    • Boyd M.R., Bacon T.H., Sutton D., et al. Antiherpesvirus activity of 9-(4-hydroxy-3-hydroxy-methylbut-1-yl)guanine (BRL 39123) in cell culture. Antimicrob Agents Chemother 1987, 31:1238-1242.
    • (1987) Antimicrob Agents Chemother , vol.31 , pp. 1238-1242
    • Boyd, M.R.1    Bacon, T.H.2    Sutton, D.3
  • 37
    • 0027480434 scopus 로고
    • Comparative pharmacokinetics of antiviral nucleoside analogues
    • Morse G.D., Shelton M.J., O'Donnell A.M. Comparative pharmacokinetics of antiviral nucleoside analogues. Clin Pharmacokinet 1993, 24:101-123.
    • (1993) Clin Pharmacokinet , vol.24 , pp. 101-123
    • Morse, G.D.1    Shelton, M.J.2    O'Donnell, A.M.3
  • 38
    • 0027511640 scopus 로고
    • Famciclovir and penciclovir. The mode of action of famciclovir including its conversion to penciclovir
    • Vere Hodge R.A. Famciclovir and penciclovir. The mode of action of famciclovir including its conversion to penciclovir. Antivir Chem Chemother 1993, 4:67-84.
    • (1993) Antivir Chem Chemother , vol.4 , pp. 67-84
    • Vere Hodge, R.A.1
  • 39
    • 0030840879 scopus 로고    scopus 로고
    • Invitro oxidation of famciclovir and 6-eoxypenciclovir by aldehyde oxidase from human, guinea pig, rabbit, and rat liver
    • Rashidi M.R., Smith J.A., Clarke S.E., et al. Invitro oxidation of famciclovir and 6-eoxypenciclovir by aldehyde oxidase from human, guinea pig, rabbit, and rat liver. Drug Metab Dispos 1997, 25:805-813.
    • (1997) Drug Metab Dispos , vol.25 , pp. 805-813
    • Rashidi, M.R.1    Smith, J.A.2    Clarke, S.E.3
  • 40
    • 0029161145 scopus 로고
    • Famciclovir. A review of its pharmacological properties and therapeutic efficacy in herpesvirus infection
    • Perry C.M., Wagstaff A.J. Famciclovir. A review of its pharmacological properties and therapeutic efficacy in herpesvirus infection. Drugs 1995, 50:396-415.
    • (1995) Drugs , vol.50 , pp. 396-415
    • Perry, C.M.1    Wagstaff, A.J.2
  • 41
    • 0027133478 scopus 로고
    • Pharmacokinetics of famciclovir in man
    • Pue M.A., Benet L.Z. Pharmacokinetics of famciclovir in man. Antivir Chem Chemother 1993, 4:47-55.
    • (1993) Antivir Chem Chemother , vol.4 , pp. 47-55
    • Pue, M.A.1    Benet, L.Z.2
  • 42
    • 15144355782 scopus 로고    scopus 로고
    • Synthesis and evaluation of 2-amino-9-(3-hydroxymethyl-4-alkoxycarbonyloxybut-1-yl)purines as potential prodrugs of penciclovir
    • Kim D.K., Lee N., Kim Y.W., et al. Synthesis and evaluation of 2-amino-9-(3-hydroxymethyl-4-alkoxycarbonyloxybut-1-yl)purines as potential prodrugs of penciclovir. J Med Chem 1998, 41:3435-3441.
    • (1998) J Med Chem , vol.41 , pp. 3435-3441
    • Kim, D.K.1    Lee, N.2    Kim, Y.W.3
  • 43
    • 33846589710 scopus 로고    scopus 로고
    • Mechanism of activation of b-d-2'-deoxy-2'-fluoro-2'-C-methylcytidine and inhibition of hepatitis C virus NS5B RNA polymerase
    • Murakami E., Bao H., Ramesh M., et al. Mechanism of activation of b-d-2'-deoxy-2'-fluoro-2'-C-methylcytidine and inhibition of hepatitis C virus NS5B RNA polymerase. Antimicrob Agents Chemother 2007, 51:503-509.
    • (2007) Antimicrob Agents Chemother , vol.51 , pp. 503-509
    • Murakami, E.1    Bao, H.2    Ramesh, M.3
  • 44
    • 84886073056 scopus 로고    scopus 로고
    • Potent antiviral activity of the nucleoside HCV inhibitor, R7128, in prior IFN nonresponders
    • Presented at: Frontiers in Drug Development in Viral Hepatitis (HEP-DART). Lahaina, Hawaii, USA December
    • McHutchison J.G., Reddy R., Rodriguez-Torres M., et al. Potent antiviral activity of the nucleoside HCV inhibitor, R7128, in prior IFN nonresponders. Presented at: Frontiers in Drug Development in Viral Hepatitis (HEP-DART). Lahaina, Hawaii, USA December 2007, 9-13.
    • (2007) , pp. 9-13
    • McHutchison, J.G.1    Reddy, R.2    Rodriguez-Torres, M.3
  • 45
    • 84925986479 scopus 로고    scopus 로고
    • Pharmasset
    • Pharmasset. http://www.pharmasset.com/pipeline/rg7128.aspx.
  • 46
    • 0033524026 scopus 로고    scopus 로고
    • Potent and selective inhibition of varicella-zoster virus (VZV) by nucleoside analogues with an unusual bicyclic base
    • McGuigan C., Yarnold C.J., Jones G., et al. Potent and selective inhibition of varicella-zoster virus (VZV) by nucleoside analogues with an unusual bicyclic base. J Med Chem 1999, 42:4479-4484.
    • (1999) J Med Chem , vol.42 , pp. 4479-4484
    • McGuigan, C.1    Yarnold, C.J.2    Jones, G.3
  • 47
    • 0034727849 scopus 로고    scopus 로고
    • Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain
    • McGuigan C., Barucki H., Blewett S., et al. Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain. J Med Chem 2000, 43:4993-4997.
    • (2000) J Med Chem , vol.43 , pp. 4993-4997
    • McGuigan, C.1    Barucki, H.2    Blewett, S.3
  • 48
    • 36448956849 scopus 로고    scopus 로고
    • Preclinical development of bicyclic nucleoside analogues as potent and selective inhibitors of varicella zoster virus
    • McGuigan C., Pathirana R.N., Migliore M., et al. Preclinical development of bicyclic nucleoside analogues as potent and selective inhibitors of varicella zoster virus. J Antimicrob Chemother 2007, 60:1316-1330.
    • (2007) J Antimicrob Chemother , vol.60 , pp. 1316-1330
    • McGuigan, C.1    Pathirana, R.N.2    Migliore, M.3
  • 49
    • 79952804849 scopus 로고    scopus 로고
    • Dipeptidyl peptidase IV dependent water-soluble prodrugs of highly lipophilic bicyclic nucleoside analogues
    • Alberto D.-T., Jan B., Graciela A., et al. Dipeptidyl peptidase IV dependent water-soluble prodrugs of highly lipophilic bicyclic nucleoside analogues. J Med Chem 2011, 54:1927-1942.
    • (2011) J Med Chem , vol.54 , pp. 1927-1942
    • Alberto, D.-T.1    Jan, B.2    Graciela, A.3
  • 50
    • 84862975195 scopus 로고    scopus 로고
    • Strategy in the study of nucleoside antiviral prodrugs
    • Leng L.Y., Cai Z.Q., Sun T.M. Strategy in the study of nucleoside antiviral prodrugs. Chin J Med Chem 2008, 118:310-316.
    • (2008) Chin J Med Chem , vol.118 , pp. 310-316
    • Leng, L.Y.1    Cai, Z.Q.2    Sun, T.M.3
  • 51
    • 0025552679 scopus 로고
    • Biochemical pharmacology of acyclic nucleotide analogues
    • Bronson J.J., Ho H.T., Boeck H.D., et al. Biochemical pharmacology of acyclic nucleotide analogues. Ann NY Acad Sci 1990, 616:398-407.
    • (1990) Ann NY Acad Sci , vol.616 , pp. 398-407
    • Bronson, J.J.1    Ho, H.T.2    Boeck, H.D.3
  • 52
    • 0343844454 scopus 로고    scopus 로고
    • Prodrugs of phosphates, phosphonates, and phosphinates
    • Krise J.P., Stella V.J. Prodrugs of phosphates, phosphonates, and phosphinates. Adv Drug Deliv Rev 1996, 19:287-310.
    • (1996) Adv Drug Deliv Rev , vol.19 , pp. 287-310
    • Krise, J.P.1    Stella, V.J.2
  • 53
    • 26844445742 scopus 로고    scopus 로고
    • Pro-nucleotides-recent advances in the design of efficient tools for the delivery of biologically active nucleoside monophosphates
    • Meier C. Pro-nucleotides-recent advances in the design of efficient tools for the delivery of biologically active nucleoside monophosphates. Synlett 1998, 3:233-242.
    • (1998) Synlett , vol.3 , pp. 233-242
    • Meier, C.1
  • 54
    • 0029991161 scopus 로고    scopus 로고
    • Pharmacokinetics, safety and bioavailability of HPMPC (cidofovir) in human immunodeficiency virus-infected subjects
    • Wachsman M., Petty B.G., Cundy K.C., et al. Pharmacokinetics, safety and bioavailability of HPMPC (cidofovir) in human immunodeficiency virus-infected subjects. Antivir Res 1996, 29:153-161.
    • (1996) Antivir Res , vol.29 , pp. 153-161
    • Wachsman, M.1    Petty, B.G.2    Cundy, K.C.3
  • 55
    • 0031863214 scopus 로고    scopus 로고
    • Antiretroviral efficacy and pharmacokinetics of oral bis(isopropyloxycarbonyloxymethyl)-9-(2-phosphonylmethoxypropyl) adenine in mice
    • Naesens L., Bischofberger N., Augustijns P., et al. Antiretroviral efficacy and pharmacokinetics of oral bis(isopropyloxycarbonyloxymethyl)-9-(2-phosphonylmethoxypropyl) adenine in mice. Antimicrob Agents Chemother 1998, 42:1568-1573.
    • (1998) Antimicrob Agents Chemother , vol.42 , pp. 1568-1573
    • Naesens, L.1    Bischofberger, N.2    Augustijns, P.3
  • 56
    • 0028306517 scopus 로고
    • Synthesis, oralbioavailability determination, and invitro evaluation of prodrugs of the antiviral agent 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA)
    • Starrett J.E., Tortolani D.R., Russell J., et al. Synthesis, oralbioavailability determination, and invitro evaluation of prodrugs of the antiviral agent 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA). J Med Chem 1994, 37:1857-1864.
    • (1994) J Med Chem , vol.37 , pp. 1857-1864
    • Starrett, J.E.1    Tortolani, D.R.2    Russell, J.3
  • 57
    • 0030974779 scopus 로고    scopus 로고
    • Transport, uptake, and metabolism of the bis(pivaloyloxymethyl)-ester prodrugs of 9-(2-phosphonylmethoxyethyl) adenine in an invitro cell culture system of the intestinal mucosa (Caco-2)
    • Annaert P., Kinget R., Naesens L., et al. Transport, uptake, and metabolism of the bis(pivaloyloxymethyl)-ester prodrugs of 9-(2-phosphonylmethoxyethyl) adenine in an invitro cell culture system of the intestinal mucosa (Caco-2). Pharm Res 1997, 14:492-496.
    • (1997) Pharm Res , vol.14 , pp. 492-496
    • Annaert, P.1    Kinget, R.2    Naesens, L.3
  • 58
    • 0030842430 scopus 로고    scopus 로고
    • Antihuman immunodeficiency virus (HIV) activity, safety, and pharmacokinetics of adefovir dipivoxil (9-[2-(bis-(pivaloyloxymethyl)-phosphonylmethoxyethyl] adenine) in HIV infected patients
    • Barditch-Crovo P., Toole J., Hendrix C.W., et al. Antihuman immunodeficiency virus (HIV) activity, safety, and pharmacokinetics of adefovir dipivoxil (9-[2-(bis-(pivaloyloxymethyl)-phosphonylmethoxyethyl] adenine) in HIV infected patients. J Inf Dis 1997, 176:406-413.
    • (1997) J Inf Dis , vol.176 , pp. 406-413
    • Barditch-Crovo, P.1    Toole, J.2    Hendrix, C.W.3
  • 59
    • 0142074315 scopus 로고    scopus 로고
    • Adefovir dipivoxil
    • Dando T.M., Plosker G.L. Adefovir dipivoxil. Drugs 2003, 63:2215-2234.
    • (2003) Drugs , vol.63 , pp. 2215-2234
    • Dando, T.M.1    Plosker, G.L.2
  • 60
    • 65649137155 scopus 로고    scopus 로고
    • Intravenous cidofovir for peripheral cytomegalovirus retinitis in patients with AIDS: a randomized, controlled trial
    • Lalezari J.P., Stagg R.J., Kuppermann B.D., et al. Intravenous cidofovir for peripheral cytomegalovirus retinitis in patients with AIDS: a randomized, controlled trial. Ann Pathol Lab Med 1997, 124:362-377.
    • (1997) Ann Pathol Lab Med , vol.124 , pp. 362-377
    • Lalezari, J.P.1    Stagg, R.J.2    Kuppermann, B.D.3
  • 61
    • 0031038255 scopus 로고    scopus 로고
    • Conversion of 1-[((S)-2-hydroxy-2-oxo-1,4,2-dioxaphosphorinan-5-yl) methyl] cytosine to cidofovir by an intracellular cyclic CMP phosphodiesterase
    • Mendel D.B., Cihlar T., Moon K., et al. Conversion of 1-[((S)-2-hydroxy-2-oxo-1,4,2-dioxaphosphorinan-5-yl) methyl] cytosine to cidofovir by an intracellular cyclic CMP phosphodiesterase. J Antimicrob Agents Chemother 1997, 41:641-646.
    • (1997) J Antimicrob Agents Chemother , vol.41 , pp. 641-646
    • Mendel, D.B.1    Cihlar, T.2    Moon, K.3
  • 62
    • 0042632872 scopus 로고    scopus 로고
    • Esterification of cidofovir with alkoxyalkanols increases oral bioavailability and diminishes accumulation in kidney
    • Ciesla S.L., Trahan J., Wan W.B., et al. Esterification of cidofovir with alkoxyalkanols increases oral bioavailability and diminishes accumulation in kidney. Antivir Res 2003, 59:163-171.
    • (2003) Antivir Res , vol.59 , pp. 163-171
    • Ciesla, S.L.1    Trahan, J.2    Wan, W.B.3
  • 63
    • 3342879034 scopus 로고    scopus 로고
    • Design and development of oraldrugs for the prophylaxis and treatment of smallpox infection
    • Painter G.R., Hostetler K.Y. Design and development of oraldrugs for the prophylaxis and treatment of smallpox infection. TRENDS Biotechnol 2004, 22:423-427.
    • (2004) TRENDS Biotechnol , vol.22 , pp. 423-427
    • Painter, G.R.1    Hostetler, K.Y.2
  • 64
    • 37449001266 scopus 로고    scopus 로고
    • Efficacy of therapeuticintervention with an oral ether-lipid analogue ofcidofovir (CMX001) in a lethal mousepox model
    • Parker S., Touchette E., Oberle C., et al. Efficacy of therapeuticintervention with an oral ether-lipid analogue ofcidofovir (CMX001) in a lethal mousepox model. Antivir Res 2008, 77:39-49.
    • (2008) Antivir Res , vol.77 , pp. 39-49
    • Parker, S.1    Touchette, E.2    Oberle, C.3
  • 65
    • 0942301302 scopus 로고    scopus 로고
    • Oral treatment of cowpox and vaccinia virus infections in mice with ether lipid esters of cidofovir
    • Quenelle D.C., Collins D.J., Wan W.B., et al. Oral treatment of cowpox and vaccinia virus infections in mice with ether lipid esters of cidofovir. Antimicrob Agents Chemother 2004, 48:404-412.
    • (2004) Antimicrob Agents Chemother , vol.48 , pp. 404-412
    • Quenelle, D.C.1    Collins, D.J.2    Wan, W.B.3
  • 66
    • 2142715953 scopus 로고    scopus 로고
    • Inhibitory activity of alkoxyalkyl and alkyl esters of cidofovir and cyclic cidofovir against orthopoxvirus replication invitro
    • Keith K.A., Wan W.B., Ciesla S.L., et al. Inhibitory activity of alkoxyalkyl and alkyl esters of cidofovir and cyclic cidofovir against orthopoxvirus replication invitro. Antimicrob Agents Chemother 2004, 48:1869-1871.
    • (2004) Antimicrob Agents Chemother , vol.48 , pp. 1869-1871
    • Keith, K.A.1    Wan, W.B.2    Ciesla, S.L.3
  • 67
    • 0037333556 scopus 로고    scopus 로고
    • Increased antiviral activity of 1-O-hexadecyloxypropyl-[2-14C]cidofovir in MRC-5 human lung fibroblasts is explained by unique cellular uptake and metabolism
    • Aldern K.A., Ciesla S.L., Winegarden K.L., et al. Increased antiviral activity of 1-O-hexadecyloxypropyl-[2-14C]cidofovir in MRC-5 human lung fibroblasts is explained by unique cellular uptake and metabolism. Mol Pharmacol 2003, 63:678-681.
    • (2003) Mol Pharmacol , vol.63 , pp. 678-681
    • Aldern, K.A.1    Ciesla, S.L.2    Winegarden, K.L.3
  • 69
    • 76949104697 scopus 로고    scopus 로고
    • Amidona puromycin-sensitive aminopeptidase: an antiviral prodrug activating enzyme
    • Tehlera U., Nelsona C.H., Petersonc L.W., et al. Amidona puromycin-sensitive aminopeptidase: an antiviral prodrug activating enzyme. Antivir Res 2010, 85:482-489.
    • (2010) Antivir Res , vol.85 , pp. 482-489
    • Tehlera, U.1    Nelsona, C.H.2    Petersonc, L.W.3
  • 70
    • 0030782524 scopus 로고    scopus 로고
    • Synthesis, invitrobiological evaluation and oral bioavailability of 9-[2-(phosphonomethoxy)-propyl]adenine (PMPA) prodrugs
    • Arimilli M.N., Kim C.U., Dougherty J., et al. Synthesis, invitrobiological evaluation and oral bioavailability of 9-[2-(phosphonomethoxy)-propyl]adenine (PMPA) prodrugs. Antivir Chem Chemother 1997, 8:557-564.
    • (1997) Antivir Chem Chemother , vol.8 , pp. 557-564
    • Arimilli, M.N.1    Kim, C.U.2    Dougherty, J.3
  • 71
    • 0031430945 scopus 로고    scopus 로고
    • Metabolism and pharmacokinetics of novel oral prodrugs of 9-[(R)-2-(phosphonomethoxy)propyl]adenine (PMPA) in dogs
    • Shaw J.P., Sueoka C.M., Oliyai R., et al. Metabolism and pharmacokinetics of novel oral prodrugs of 9-[(R)-2-(phosphonomethoxy)propyl]adenine (PMPA) in dogs. Pharm Res 1997, 14:1824-1829.
    • (1997) Pharm Res , vol.14 , pp. 1824-1829
    • Shaw, J.P.1    Sueoka, C.M.2    Oliyai, R.3
  • 72
    • 0034806946 scopus 로고    scopus 로고
    • Phase I/II trial of the pharmacokinetics, safety, and antiviral activity of tenofovir dioproxil fumarate in human immunodeficiency virus infected adults
    • Barditch-Crovo P., Deeks S.G., Dollier A., et al. Phase I/II trial of the pharmacokinetics, safety, and antiviral activity of tenofovir dioproxil fumarate in human immunodeficiency virus infected adults. Antimicrob Agents Chemother 2001, 45:2733-2739.
    • (2001) Antimicrob Agents Chemother , vol.45 , pp. 2733-2739
    • Barditch-Crovo, P.1    Deeks, S.G.2    Dollier, A.3
  • 73
    • 0026561408 scopus 로고
    • Aryl phosphates derivatives of AZT retain activity against HIV1 in cell lines which are resistant to the action of AZT
    • McGuigan C., Pathirana R.N., Mahmood N., et al. Aryl phosphates derivatives of AZT retain activity against HIV1 in cell lines which are resistant to the action of AZT. Antivir Res 1992, 17:311-321.
    • (1992) Antivir Res , vol.17 , pp. 311-321
    • McGuigan, C.1    Pathirana, R.N.2    Mahmood, N.3
  • 74
    • 4344590715 scopus 로고    scopus 로고
    • Improvedantiviral activity of the aryloxymethoxyalaninyl phosphoramidate (APA) prodrug of abacavir (ABC) isdueto the formation of markedly increased carbovir 5'-triphosphate metabolite levels
    • Balzarini J., Aquaro S., Hassan-Abdallah A., et al. Improvedantiviral activity of the aryloxymethoxyalaninyl phosphoramidate (APA) prodrug of abacavir (ABC) isdueto the formation of markedly increased carbovir 5'-triphosphate metabolite levels. FEBS Lett 2004, 573:38-44.
    • (2004) FEBS Lett , vol.573 , pp. 38-44
    • Balzarini, J.1    Aquaro, S.2    Hassan-Abdallah, A.3
  • 75
    • 18244398917 scopus 로고    scopus 로고
    • Selective intracellular activation of a novel prodrug of the human immunodeficiency virus reverse transcriptase inhibitor tenofovir leads to preferential distribution and accumulation in lymphatic tissue
    • Lee W.A., He G.X., Eisenberg E., et al. Selective intracellular activation of a novel prodrug of the human immunodeficiency virus reverse transcriptase inhibitor tenofovir leads to preferential distribution and accumulation in lymphatic tissue. Antimicrob Agents Chemother 2005, 49:1898-1906.
    • (2005) Antimicrob Agents Chemother , vol.49 , pp. 1898-1906
    • Lee, W.A.1    He, G.X.2    Eisenberg, E.3
  • 77
    • 20844434037 scopus 로고    scopus 로고
    • Application of phosphoramidate pronucleotide technology to abacavir leads to a significant enhancement of antiviral potency
    • McGuigan C., Harris S.A., Daluge S.M., et al. Application of phosphoramidate pronucleotide technology to abacavir leads to a significant enhancement of antiviral potency. J Med Chem 2005, 48:3504-3515.
    • (2005) J Med Chem , vol.48 , pp. 3504-3515
    • McGuigan, C.1    Harris, S.A.2    Daluge, S.M.3
  • 79
    • 0036462584 scopus 로고    scopus 로고
    • Determinants of resistance to 2',2'-difluorodeoxycytidine (gemcitabine)
    • Bergman A.M., Pinedo H.M., Peters G.J. Determinants of resistance to 2',2'-difluorodeoxycytidine (gemcitabine). Drug Resist Updat 2002, 5:19-33.
    • (2002) Drug Resist Updat , vol.5 , pp. 19-33
    • Bergman, A.M.1    Pinedo, H.M.2    Peters, G.J.3
  • 81
    • 33846178254 scopus 로고    scopus 로고
    • Squalenoyl nanomedicines as potential therapeutics
    • Couvreur P., Stella B., Reddy L.H., et al. Squalenoyl nanomedicines as potential therapeutics. Nano Lett 2006, 6:2544-2548.
    • (2006) Nano Lett , vol.6 , pp. 2544-2548
    • Couvreur, P.1    Stella, B.2    Reddy, L.H.3
  • 82
    • 84877745217 scopus 로고    scopus 로고
    • Preclinical absorption, distribution, metabolism, and excretion of an oral amide prodrug of gemcitabine designed to deliver prolonged systemic exposure
    • Wickremsinhe E., Bao J.Q., Smith R., et al. Preclinical absorption, distribution, metabolism, and excretion of an oral amide prodrug of gemcitabine designed to deliver prolonged systemic exposure. Pharmaceutics 2013, 5:261-276.
    • (2013) Pharmaceutics , vol.5 , pp. 261-276
    • Wickremsinhe, E.1    Bao, J.Q.2    Smith, R.3
  • 83
    • 84878662338 scopus 로고    scopus 로고
    • Phase I study of oral gemcitabine prodrug (LY2334737) in Japanese patients with advanced solid tumors
    • Yamamoto N., Nokihara H., Yamada Y., et al. Phase I study of oral gemcitabine prodrug (LY2334737) in Japanese patients with advanced solid tumors. Cancer Chemother Pharmacol 2013, 71:1645-1655.
    • (2013) Cancer Chemother Pharmacol , vol.71 , pp. 1645-1655
    • Yamamoto, N.1    Nokihara, H.2    Yamada, Y.3
  • 84
    • 0030982931 scopus 로고    scopus 로고
    • 1592U89, a novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity
    • Daluge S.M., Good S.S., Faletto M.B., et al. 1592U89, a novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity. Antimicrob Agents Chemother 1997, 41:1082-1093.
    • (1997) Antimicrob Agents Chemother , vol.41 , pp. 1082-1093
    • Daluge, S.M.1    Good, S.S.2    Faletto, M.B.3
  • 85
    • 0032766290 scopus 로고    scopus 로고
    • Abacavir: absolute bioavailability, bioequivalence of three oral formulations, and effect of food
    • Chittick G.E., Gillotin C., McDowell J.A., et al. Abacavir: absolute bioavailability, bioequivalence of three oral formulations, and effect of food. Pharmacotherapy 1999, 19:932-942.
    • (1999) Pharmacotherapy , vol.19 , pp. 932-942
    • Chittick, G.E.1    Gillotin, C.2    McDowell, J.A.3
  • 86
    • 0030903443 scopus 로고    scopus 로고
    • Unique intracellular activation of the potent anti-human immunodeficiency virus agent 1592 U89
    • Faletto M.B., Miller W.H., Garvey E.P., et al. Unique intracellular activation of the potent anti-human immunodeficiency virus agent 1592 U89. Antimicrob Agents Chemother 1997, 41:1099-1107.
    • (1997) Antimicrob Agents Chemother , vol.41 , pp. 1099-1107
    • Faletto, M.B.1    Miller, W.H.2    Garvey, E.P.3
  • 87
    • 0141928585 scopus 로고    scopus 로고
    • Ribavirin, viramidine and adenosine-deaminase-catalysed drug activation: Implication for nucleoside prodrug design
    • Wu J.Z., Lin C.C., Hong Z. Ribavirin, viramidine and adenosine-deaminase-catalysed drug activation: Implication for nucleoside prodrug design. J Antimicrob Chemother 2003, 52:543-546.
    • (2003) J Antimicrob Chemother , vol.52 , pp. 543-546
    • Wu, J.Z.1    Lin, C.C.2    Hong, Z.3
  • 88
    • 0042675191 scopus 로고    scopus 로고
    • Pharmacokinetics and metabolism of [14C] viramidine in rats and cynomolgus monkeys
    • Lin C.C., Luu K., Lourenco D., et al. Pharmacokinetics and metabolism of [14C] viramidine in rats and cynomolgus monkeys. Antimicrob Agents Chemother 2003, 47:2458-2463.
    • (2003) Antimicrob Agents Chemother , vol.47 , pp. 2458-2463
    • Lin, C.C.1    Luu, K.2    Lourenco, D.3
  • 89
    • 33745587585 scopus 로고    scopus 로고
    • Absorption, metabolism, and excretion of [14C] viramidine in humans
    • Lin C.C., Xu C., Zhu N., et al. Absorption, metabolism, and excretion of [14C] viramidine in humans. Antimicrob Agents Chemother 2006, 50:2368-2373.
    • (2006) Antimicrob Agents Chemother , vol.50 , pp. 2368-2373
    • Lin, C.C.1    Xu, C.2    Zhu, N.3
  • 90
    • 0041736493 scopus 로고    scopus 로고
    • Viramidine, a prodrug of ribavirin, shows better liver-targeting properties and safety profiles than ribavirin in animals
    • Lin C.C., Yeh L.T., Vitarella D., H., et al. Viramidine, a prodrug of ribavirin, shows better liver-targeting properties and safety profiles than ribavirin in animals. Antivir Chem Chemother 2003, 14:145-152.
    • (2003) Antivir Chem Chemother , vol.14 , pp. 145-152
    • Lin, C.C.1    Yeh, L.T.2    Vitarella, D.H.3
  • 91
    • 33747775068 scopus 로고    scopus 로고
    • The safety and efficacy of viramidine plus pegylated interferon alpha-2b versus ribavirin plus pegylated interferon alpha-2b in therapy-naïve patients infected with HCV phase 3 results
    • Benhamou Y., Pockros P., Rodriguez-Torres M., et al. The safety and efficacy of viramidine plus pegylated interferon alpha-2b versus ribavirin plus pegylated interferon alpha-2b in therapy-naïve patients infected with HCV phase 3 results. J Hepatol 2006, 44:S273.
    • (2006) J Hepatol , vol.44 , pp. S273
    • Benhamou, Y.1    Pockros, P.2    Rodriguez-Torres, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.