메뉴 건너뛰기




Volumn 57, Issue 3, 2014, Pages 759-769

Development of novel potent orally bioavailable oseltamivir derivatives active against resistant influenza A

Author keywords

[No Author keywords available]

Indexed keywords

ADMINISTRATION, ORAL; AMIDINES; ANIMALS; ANTIVIRAL AGENTS; BIOLOGICAL AVAILABILITY; DOGS; DRUG RESISTANCE, VIRAL; GUANIDINES; HUMANS; INFLUENZA A VIRUS, H1N1 SUBTYPE; INFLUENZA A VIRUS, H3N2 SUBTYPE; MADIN DARBY CANINE KIDNEY CELLS; MALE; MOLECULAR DOCKING SIMULATION; MUTATION; NEURAMINIDASE; OSELTAMIVIR; PRODRUGS; PROTEIN BINDING; RATS; RATS, SPRAGUE-DAWLEY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE;

EID: 84894094139     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm401492x     Document Type: Article
Times cited : (77)

References (46)
  • 1
    • 84894081059 scopus 로고    scopus 로고
    • World Health Organization Influenza Fact Sheet 211; World Health Organization: Geneva.
    • World Health Organization Influenza Fact Sheet 211; World Health Organization: Geneva, 2009; http://www.who.int/mediacentre/factsheets/fs211/en/.
    • (2009)
  • 4
    • 0344395604 scopus 로고    scopus 로고
    • Are we ready for pandemic influenza?
    • Webby, R. J.; Webster, R. G. Are we ready for pandemic influenza? Science 2003, 302, 1519-1522
    • (2003) Science , vol.302 , pp. 1519-1522
    • Webby, R.J.1    Webster, R.G.2
  • 6
    • 84864228530 scopus 로고    scopus 로고
    • Antivirals targeting influenza A virus
    • Das, K. Antivirals targeting influenza A virus J. Med. Chem. 2012, 55, 6263-6277
    • (2012) J. Med. Chem. , vol.55 , pp. 6263-6277
    • Das, K.1
  • 7
    • 33751517736 scopus 로고    scopus 로고
    • Antiviral agents active against influenza A viruses
    • De Clercq, E. Antiviral agents active against influenza A viruses Nat. Rev. Drug Discovery 2006, 5, 1015-1025
    • (2006) Nat. Rev. Drug Discovery , vol.5 , pp. 1015-1025
    • De Clercq, E.1
  • 9
    • 84866303453 scopus 로고    scopus 로고
    • Supply of neuraminidase inhibitors related to reduced influenza A (H1N1) mortality during the 2009-2010 H1N1 pandemic: An ecological study
    • Miller, P. E.; Rambachan, A.; Hubbard, R. J.; Li, J.; Meyer, A. E.; Stephens, P.; Mounts, A. W.; Rolfes, M. A.; Penn, C. R. Supply of neuraminidase inhibitors related to reduced influenza A (H1N1) mortality during the 2009-2010 H1N1 pandemic: an ecological study PloS One 2012, 7, e43491
    • (2012) PloS One , vol.7 , pp. 43491
    • Miller, P.E.1    Rambachan, A.2    Hubbard, R.J.3    Li, J.4    Meyer, A.E.5    Stephens, P.6    Mounts, A.W.7    Rolfes, M.A.8    Penn, C.R.9
  • 10
    • 0027162942 scopus 로고
    • 4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid is a highly effective inhibitor both of the sialidase (neuraminidase) and of growth of a wide range of influenza A and B viruses in vitro
    • Woods, J. M.; Bethell, R. C.; Coates, J. A.; Healy, N.; Hiscox, S. A.; Pearson, B. A.; Ryan, D. M.; Ticehurst, J.; Tilling, J.; Walcott, S. M.; Penn, C. R. 4-Guanidino-2,4-dideoxy-2,3-dehydro-N-acetylneuraminic acid is a highly effective inhibitor both of the sialidase (neuraminidase) and of growth of a wide range of influenza A and B viruses in vitro Antimicrob. Agents Chemother. 1993, 37, 1473-1479
    • (1993) Antimicrob. Agents Chemother. , vol.37 , pp. 1473-1479
    • Woods, J.M.1    Bethell, R.C.2    Coates, J.A.3    Healy, N.4    Hiscox, S.A.5    Pearson, B.A.6    Ryan, D.M.7    Ticehurst, J.8    Tilling, J.9    Walcott, S.M.10    Penn, C.R.11
  • 11
    • 78751692669 scopus 로고    scopus 로고
    • Laninamivir and its prodrug, CS-8958: Long-acting neuraminidase inhibitors for the treatment of influenza
    • Yamashita, M. Laninamivir and its prodrug, CS-8958: long-acting neuraminidase inhibitors for the treatment of influenza Antimicrob. Agents Chemother. 2010, 21, 71-84
    • (2010) Antimicrob. Agents Chemother. , vol.21 , pp. 71-84
    • Yamashita, M.1
  • 12
    • 77149156604 scopus 로고    scopus 로고
    • Laninamivir prodrug CS-8958, a long-acting neuraminidase inhibitor, shows superior anti-influenza virus activity after a single administration
    • Kubo, S.; Tomozawa, T.; Kakuta, M.; Tokumitsu, A.; Yamashita, M. Laninamivir prodrug CS-8958, a long-acting neuraminidase inhibitor, shows superior anti-influenza virus activity after a single administration Antimicrob. Agents Chemother. 2010, 54, 1256-1264
    • (2010) Antimicrob. Agents Chemother. , vol.54 , pp. 1256-1264
    • Kubo, S.1    Tomozawa, T.2    Kakuta, M.3    Tokumitsu, A.4    Yamashita, M.5
  • 14
    • 73349121665 scopus 로고    scopus 로고
    • The Emergency Use Authorization of peramivir for treatment of 2009 H1N1 influenza
    • Birnkrant, D.; Cox, E. The Emergency Use Authorization of peramivir for treatment of 2009 H1N1 influenza N. Engl. J. Med. 2009, 361, 2204-2207
    • (2009) N. Engl. J. Med. , vol.361 , pp. 2204-2207
    • Birnkrant, D.1    Cox, E.2
  • 15
    • 77958476873 scopus 로고    scopus 로고
    • The role of clinical pharmacology in supporting the emergency use authorization of an unapproved anti-influenza drug, peramivir
    • Arya, V.; Carter, W. W.; Robertson, S. M. The role of clinical pharmacology in supporting the emergency use authorization of an unapproved anti-influenza drug, peramivir Clin. Pharmacol. Ther. 2010, 88, 587-589
    • (2010) Clin. Pharmacol. Ther. , vol.88 , pp. 587-589
    • Arya, V.1    Carter, W.W.2    Robertson, S.M.3
  • 17
    • 84860334106 scopus 로고    scopus 로고
    • Neuraminidase inhibitor resistance in influenza viruses and laboratory testing methods
    • Nguyen, H. T.; Fry, A. M.; Gubareva, L. V. Neuraminidase inhibitor resistance in influenza viruses and laboratory testing methods Antivir. Ther. 2012, 17, 159-173
    • (2012) Antivir. Ther. , vol.17 , pp. 159-173
    • Nguyen, H.T.1    Fry, A.M.2    Gubareva, L.V.3
  • 18
    • 77952576118 scopus 로고    scopus 로고
    • Pharmacokinetics of oseltamivir: An oral antiviral for the treatment and prophylaxis of influenza in diverse populations
    • Davies, B. E. Pharmacokinetics of oseltamivir: an oral antiviral for the treatment and prophylaxis of influenza in diverse populations J. Antimicrob. Chemother. 2010, 65 (Suppl 2) ii5-ii10
    • (2010) J. Antimicrob. Chemother. , vol.65 , Issue.SUPPL. 2
    • Davies, B.E.1
  • 19
    • 0032996541 scopus 로고    scopus 로고
    • Pharmacokinetics of zanamivir after intravenous, oral, inhaled or intranasal administration to healthy volunteers
    • Cass, L. M.; Efthymiopoulos, C.; Bye, A. Pharmacokinetics of zanamivir after intravenous, oral, inhaled or intranasal administration to healthy volunteers Clin. Pharmacokinet. 1999, 36 (Suppl 1) 1-11
    • (1999) Clin. Pharmacokinet. , vol.36 , Issue.SUPPL. 1 , pp. 1-11
    • Cass, L.M.1    Efthymiopoulos, C.2    Bye, A.3
  • 24
    • 79961172983 scopus 로고    scopus 로고
    • Intramolecular ion-pair prodrugs of zanamivir and guanidino-oseltamivir
    • Liu, K. C.; Lee, P. S.; Wang, S. Y.; Cheng, Y. S.; Fang, J. M.; Wong, C. H. Intramolecular ion-pair prodrugs of zanamivir and guanidino-oseltamivir Bioorg. Med. Chem. 2011, 19, 4796-4802
    • (2011) Bioorg. Med. Chem. , vol.19 , pp. 4796-4802
    • Liu, K.C.1    Lee, P.S.2    Wang, S.Y.3    Cheng, Y.S.4    Fang, J.M.5    Wong, C.H.6
  • 25
    • 77955235031 scopus 로고    scopus 로고
    • Enabling the intestinal absorption of highly polar antiviral agents: Ion-pair facilitated membrane permeation of zanamivir heptyl ester and guanidino oseltamivir
    • Miller, J. M.; Dahan, A.; Gupta, D.; Varghese, S.; Amidon, G. L. Enabling the intestinal absorption of highly polar antiviral agents: ion-pair facilitated membrane permeation of zanamivir heptyl ester and guanidino oseltamivir Mol. Pharmaceutics 2010, 7, 1223-1234
    • (2010) Mol. Pharmaceutics , vol.7 , pp. 1223-1234
    • Miller, J.M.1    Dahan, A.2    Gupta, D.3    Varghese, S.4    Amidon, G.L.5
  • 26
    • 84873325984 scopus 로고    scopus 로고
    • Increasing oral absorption of polar neuraminidase inhibitors: A prodrug transporter approach applied to oseltamivir analogue
    • Gupta, D.; Varghese Gupta, S.; Dahan, A.; Tsume, Y.; Hilfinger, J.; Lee, K. D.; Amidon, G. L. Increasing oral absorption of polar neuraminidase inhibitors: a prodrug transporter approach applied to oseltamivir analogue Mol. Pharmacol. 2013, 10, 512-522
    • (2013) Mol. Pharmacol. , vol.10 , pp. 512-522
    • Gupta, D.1    Varghese Gupta, S.2    Dahan, A.3    Tsume, Y.4    Hilfinger, J.5    Lee, K.D.6    Amidon, G.L.7
  • 27
    • 24944473872 scopus 로고    scopus 로고
    • Metabolism of N-hydroxyguanidines (N-hydroxydebrisoquine) in human and porcine hepatocytes: Reduction and formation of glucuronides
    • Froehlich, A. K.; Girreser, U.; Clement, B. Metabolism of N-hydroxyguanidines (N-hydroxydebrisoquine) in human and porcine hepatocytes: reduction and formation of glucuronides Drug Metab. Dispos. 2005, 33, 1532-1537
    • (2005) Drug Metab. Dispos. , vol.33 , pp. 1532-1537
    • Froehlich, A.K.1    Girreser, U.2    Clement, B.3
  • 28
    • 0027141919 scopus 로고
    • Cytochrome P450 dependent N-hydroxylation of a guanidine (debrisoquine), microsomal catalysed reduction and further oxidation of the N-hydroxy-guanidine metabolite to the urea derivative. Similarity with the oxidation of arginine to citrulline and nitric oxide
    • Clement, B.; Schultze-Mosgau, M. H.; Wohlers, H. Cytochrome P450 dependent N-hydroxylation of a guanidine (debrisoquine), microsomal catalysed reduction and further oxidation of the N-hydroxy-guanidine metabolite to the urea derivative. Similarity with the oxidation of arginine to citrulline and nitric oxide Biochem. Pharmacol. 1993, 46, 2249-2267
    • (1993) Biochem. Pharmacol. , vol.46 , pp. 2249-2267
    • Clement, B.1    Schultze-Mosgau, M.H.2    Wohlers, H.3
  • 29
    • 79959787734 scopus 로고    scopus 로고
    • Prodrug design for the potent cardiovascular agent Nomega-hydroxy- l -arginine (NOHA): Synthetic approaches and physicochemical characterization
    • Schade, D.; Kotthaus, J.; Klein, N.; Kotthaus, J.; Clement, B. Prodrug design for the potent cardiovascular agent Nomega-hydroxy- l -arginine (NOHA): synthetic approaches and physicochemical characterization Org. Biomol. Chem. 2011, 9, 5249-5259
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 5249-5259
    • Schade, D.1    Kotthaus, J.2    Klein, N.3    Kotthaus, J.4    Clement, B.5
  • 30
    • 0029967158 scopus 로고    scopus 로고
    • Microsomal catalyzed N-hydroxylation of guanabenz and reduction of the N-hydroxylated metabolite: Characterization of the two reactions and genotoxic potential of guanoxabenz
    • Clement, B.; Demesmaeker, M.; Linne, S. Microsomal catalyzed N-hydroxylation of guanabenz and reduction of the N-hydroxylated metabolite: characterization of the two reactions and genotoxic potential of guanoxabenz Chem. Res. Toxicol. 1996, 9, 682-688
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 682-688
    • Clement, B.1    Demesmaeker, M.2    Linne, S.3
  • 31
    • 0031021264 scopus 로고    scopus 로고
    • S -2-Naphthylmethyl Thioacetimidste Hydrobromide: A New Odorless Reagent for the Mild Synthesis of Substituted Acetamidines
    • Shearer, B. G.; Oplinger, J. A.; Lee, S. S -2-Naphthylmethyl Thioacetimidste Hydrobromide: A New Odorless Reagent For The Mild Synthesis Of Substituted Acetamidines Tetrahedron Lett. 1997, 38, 179-182
    • (1997) Tetrahedron Lett. , vol.38 , pp. 179-182
    • Shearer, B.G.1    Oplinger, J.A.2    Lee, S.3
  • 32
    • 37049079777 scopus 로고
    • Stereoselective synthesis of 1,2-diols by the cycloadditive strategy: Total synthesis of (±)-exo-brevicomin and (±)- and (-)-pestalotin
    • Zhang, J.; Curran, D. P. Stereoselective synthesis of 1,2-diols by the cycloadditive strategy: total synthesis of (±)-exo-brevicomin and (±)- and (-)-pestalotin J. Chem. Soc. Perkin 1 1991, 11, 2627-2631
    • (1991) J. Chem. Soc. Perkin 1 , vol.11 , pp. 2627-2631
    • Zhang, J.1    Curran, D.P.2
  • 33
    • 79953667599 scopus 로고    scopus 로고
    • Novel neuraminidase inhibitors: Identification, biological evaluation and investigations of the binding mode
    • Kirchmair, J.; Rollinger, J. M.; Liedl, K. R.; Seidel, N.; Krumbholz, A.; Schmidtke, M. Novel neuraminidase inhibitors: identification, biological evaluation and investigations of the binding mode Future Med. Chem. 2011, 3, 437-450
    • (2011) Future Med. Chem. , vol.3 , pp. 437-450
    • Kirchmair, J.1    Rollinger, J.M.2    Liedl, K.R.3    Seidel, N.4    Krumbholz, A.5    Schmidtke, M.6
  • 34
    • 62049086175 scopus 로고    scopus 로고
    • Different neuraminidase inhibitor susceptibilities of human H1N1, H1N2, and H3N2 influenza A viruses isolated in Germany from 2001 to 2005/2006
    • Bauer, K.; Richter, M.; Wutzler, P.; Schmidtke, M. Different neuraminidase inhibitor susceptibilities of human H1N1, H1N2, and H3N2 influenza A viruses isolated in Germany from 2001 to 2005/2006 Antivir. Res. 2009, 82, 34-41
    • (2009) Antivir. Res. , vol.82 , pp. 34-41
    • Bauer, K.1    Richter, M.2    Wutzler, P.3    Schmidtke, M.4
  • 36
    • 84876003028 scopus 로고    scopus 로고
    • Influenza virus resistance to neuraminidase inhibitors
    • Samson, M.; Pizzorno, A.; Abed, Y.; Boivin, G. Influenza virus resistance to neuraminidase inhibitors Antivir. Res. 2013, 98, 174-185
    • (2013) Antivir. Res. , vol.98 , pp. 174-185
    • Samson, M.1    Pizzorno, A.2    Abed, Y.3    Boivin, G.4
  • 37
    • 0033385681 scopus 로고    scopus 로고
    • Clinical pharmacokinetics of the prodrug oseltamivir and its active metabolite Ro 64-0802
    • He, G.; Massarella, J.; Ward, P. Clinical pharmacokinetics of the prodrug oseltamivir and its active metabolite Ro 64-0802 Clin. Pharmacokinet. 1999, 37, 471-484
    • (1999) Clin. Pharmacokinet. , vol.37 , pp. 471-484
    • He, G.1    Massarella, J.2    Ward, P.3
  • 38
    • 0030822685 scopus 로고    scopus 로고
    • Penetration of GS4071, a novel influenza neuraminidase inhibitor, into rat bronchoalveolar lining fluid following oral administration of the prodrug GS4104
    • Eisenberg, E. J.; Bidgood, A.; Cundy, K. C. Penetration of GS4071, a novel influenza neuraminidase inhibitor, into rat bronchoalveolar lining fluid following oral administration of the prodrug GS4104 Antimicrob. Agents Chemother. 1997, 41, 1949-1952
    • (1997) Antimicrob. Agents Chemother. , vol.41 , pp. 1949-1952
    • Eisenberg, E.J.1    Bidgood, A.2    Cundy, K.C.3
  • 39
    • 0037403707 scopus 로고    scopus 로고
    • Characterization of in vitro biotransformation of new, orally active, direct thrombin inhibitor ximelagatran, an amidoxime and ester prodrug
    • Clement, B.; Lopian, K. Characterization of in vitro biotransformation of new, orally active, direct thrombin inhibitor ximelagatran, an amidoxime and ester prodrug Drug Metab. Dispos. 2003, 31, 645-651
    • (2003) Drug Metab. Dispos. , vol.31 , pp. 645-651
    • Clement, B.1    Lopian, K.2
  • 40
  • 41
    • 0004006597 scopus 로고
    • Hydroxylamine base was set free from its hydrochloride salt with sodium ethanolate. In, 3 rd ed. Brauer, G. Ferdinand Enke Verlag: Stuttgart, Vol.
    • Steudel, R.; Schenk, P. W. Hydroxylamine base was set free from its hydrochloride salt with sodium ethanolate. In Handbuch der Präparativen Anorganischen Chemie, 3 rd ed.; Brauer, G., Ed.; Ferdinand Enke Verlag: Stuttgart, 1975; Vol. 1, p 464.
    • (1975) Handbuch der Präparativen Anorganischen Chemie , vol.1 , pp. 464
    • Steudel, R.1    Schenk, P.W.2
  • 43
    • 84894038446 scopus 로고    scopus 로고
    • Molecular Operating Environment (MOE); Chemical Computing Group Inc: Montreal; (accessed September 9, 2013).
    • Molecular Operating Environment (MOE); Chemical Computing Group Inc: Montreal; http://www.chemcomp.com. (accessed September 9, 2013).
  • 44
    • 0031552362 scopus 로고    scopus 로고
    • Development and validation of a genetic algorithm for flexible docking
    • Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking J. Mol. Biol. 1997, 267, 727-748
    • (1997) J. Mol. Biol. , vol.267 , pp. 727-748
    • Jones, G.1    Willett, P.2    Glen, R.C.3    Leach, A.R.4    Taylor, R.5
  • 45
    • 33745158157 scopus 로고
    • A simple method of estimating fifty percent endpoints
    • Reed, L.; Muench, H. A simple method of estimating fifty percent endpoints Am. J. Hyg. 1938, 27, 493-497
    • (1938) Am. J. Hyg. , vol.27 , pp. 493-497
    • Reed, L.1    Muench, H.2
  • 46
    • 0035002220 scopus 로고    scopus 로고
    • A rapid assay for evaluation of antiviral activity against coxsackie virus B3, influenza virus A, and herpes simplex virus type 1
    • Schmidtke, M.; Schnittler, U.; Jahn, B.; Dahse, H.; Stelzner, A. A rapid assay for evaluation of antiviral activity against coxsackie virus B3, influenza virus A, and herpes simplex virus type 1 J. Virol. Methods 2001, 95, 133-143
    • (2001) J. Virol. Methods , vol.95 , pp. 133-143
    • Schmidtke, M.1    Schnittler, U.2    Jahn, B.3    Dahse, H.4    Stelzner, A.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.