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Volumn 20, Issue 11, 2007, Pages 1709-1717

Species-specific, P450- and sulfotransferase-mediated novel ring contraction of a naphthyridine-N-oxide compound in cynomolgus monkey

Author keywords

[No Author keywords available]

Indexed keywords

5,10 DIHYDROBENZO[B][1,8]NAPHTHYRIDIN N OXIDE; BMSA 78277; DRUG METABOLITE; NAPHTHYRIDINE DERIVATIVE; NAPHTHYRIDINE N OXIDE; OXYGEN 18; RNA DIRECTED DNA POLYMERASE INHIBITOR; SULFOTRANSFERASE; UNCLASSIFIED DRUG; WATER;

EID: 37249048136     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx700170q     Document Type: Article
Times cited : (6)

References (24)
  • 1
    • 33845792941 scopus 로고    scopus 로고
    • Safety assessment of stable drug metabolites
    • Guengerich, F. P. (2006) Safety assessment of stable drug metabolites. Chem. Res. Toxicol. 19, 1559-1560.
    • (2006) Chem. Res. Toxicol , vol.19 , pp. 1559-1560
    • Guengerich, F.P.1
  • 2
    • 0034973773 scopus 로고    scopus 로고
    • Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity
    • Guengerich, F. P. (2001) Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem. Res. Toxicol. 14, 611-650.
    • (2001) Chem. Res. Toxicol , vol.14 , pp. 611-650
    • Guengerich, F.P.1
  • 3
    • 37249002062 scopus 로고    scopus 로고
    • Srivastava, A. S., Tarby, C. M., Johnson, B. M., Rajagopal, B., Curry, M., Lin, Q., Wang, H., Cocuzza, A. J., Bilder, D. M., McHugh, R. J., Patel, M., Bacheler, L. T., Diamond, S., Jeffrey, S., Klabe, R. M., Cordova, B. C., Garber, S., Logue, K., Erickson-Viitanen, S., Trainor, G. L., and Rodgers, J. D. (2005) New and improved 5,10-dihydrobenzo[b][1,8]naphthyridine-N-oxides as the next generation NNRTI's with better activity profiles against clinically relevant HIV-1 mutants. Abstracts of Papers, 230th ACS National Meeting, Washington, D.C., Aug 28-Sept 1, 2005.
    • Srivastava, A. S., Tarby, C. M., Johnson, B. M., Rajagopal, B., Curry, M., Lin, Q., Wang, H., Cocuzza, A. J., Bilder, D. M., McHugh, R. J., Patel, M., Bacheler, L. T., Diamond, S., Jeffrey, S., Klabe, R. M., Cordova, B. C., Garber, S., Logue, K., Erickson-Viitanen, S., Trainor, G. L., and Rodgers, J. D. (2005) New and improved 5,10-dihydrobenzo[b][1,8]naphthyridine-N-oxides as the next generation NNRTI's with better activity profiles against clinically relevant HIV-1 mutants. Abstracts of Papers, 230th ACS National Meeting, Washington, D.C., Aug 28-Sept 1, 2005.
  • 4
    • 37249035403 scopus 로고    scopus 로고
    • Tricyclic Compounds Useful as HIV Reverse Transcriptase Inhibitors
    • WO Patent 2002085365
    • Johnson, B. L., Rodgers, J. D., Lin, Q., and Srivastava, A. S. (2002)Tricyclic Compounds Useful as HIV Reverse Transcriptase Inhibitors. WO Patent 2002085365.
    • (2002)
    • Johnson, B.L.1    Rodgers, J.D.2    Lin, Q.3    Srivastava, A.S.4
  • 5
    • 0003909064 scopus 로고    scopus 로고
    • Woolf, T. F, Ed, 1st ed, Marcel Dekker, Inc, New York
    • Woolf, T. F., Ed. (1999) Handbook of Drug Metabolism, 1st ed., Marcel Dekker, Inc., New York.
    • (1999) Handbook of Drug Metabolism
  • 6
    • 0042348003 scopus 로고    scopus 로고
    • A mass spectrometry study of tirapazamine and its metabolites. Insights into the mechanism of metabolic transformations and the characterization of reaction intermediates
    • Zagorevskii, D., Song, M., Breneman, C., Yuan, Y., Fuchs, T., Gates, K. S., and Greenlief, C. M. (2003) A mass spectrometry study of tirapazamine and its metabolites. Insights into the mechanism of metabolic transformations and the characterization of reaction intermediates. J. Am. Soc. Mass Spectrom. 14, 881-892.
    • (2003) J. Am. Soc. Mass Spectrom , vol.14 , pp. 881-892
    • Zagorevskii, D.1    Song, M.2    Breneman, C.3    Yuan, Y.4    Fuchs, T.5    Gates, K.S.6    Greenlief, C.M.7
  • 7
    • 0023845140 scopus 로고
    • Determination of boldenone sulfoconjugate and related steroid sulfates in equine urine by high-performance liquid chromatography/tandem mass spectrometry
    • Weidolf, L. O. G., Lee, E. D., and Henion, J. D. (1988) Determination of boldenone sulfoconjugate and related steroid sulfates in equine urine by high-performance liquid chromatography/tandem mass spectrometry. Biomed. Environ. Mass Spectrom. 15, 283-289.
    • (1988) Biomed. Environ. Mass Spectrom , vol.15 , pp. 283-289
    • Weidolf, L.O.G.1    Lee, E.D.2    Henion, J.D.3
  • 9
    • 0025651074 scopus 로고
    • Reaction pathways for biodehalogenation of fluorinated anilines
    • Rietjens, I. M., Tyrakowska, B., Veeger, C., and Vervoort, J. (1990) Reaction pathways for biodehalogenation of fluorinated anilines. Eur. J. Biochem. 194, 945-954.
    • (1990) Eur. J. Biochem , vol.194 , pp. 945-954
    • Rietjens, I.M.1    Tyrakowska, B.2    Veeger, C.3    Vervoort, J.4
  • 10
    • 0038128341 scopus 로고    scopus 로고
    • Metabolism of (S)-5,6-difluoro4-cyclopropylethynyl-4-trifluoromethyl-3, 4-dihydro-2(1H)- quinazolinone, a non-nucleoside reverse transcriptase inhibitor, in human liver microsomes. Metabolic activation and enzyme kinetics
    • Chen, H., Chen, W., Gan, L.-S., and Mutlib Abdul, E. (2003) Metabolism of (S)-5,6-difluoro4-cyclopropylethynyl-4-trifluoromethyl-3, 4-dihydro-2(1H)- quinazolinone, a non-nucleoside reverse transcriptase inhibitor, in human liver microsomes. Metabolic activation and enzyme kinetics. Drug Metab. Dispos. 31, 122-132.
    • (2003) Drug Metab. Dispos , vol.31 , pp. 122-132
    • Chen, H.1    Chen, W.2    Gan, L.-S.3    Mutlib Abdul, E.4
  • 11
    • 33845769325 scopus 로고    scopus 로고
    • Safety assessment of drug metabolites: Characterization of chemically stable metabolites
    • Humphreys, W. G., and Unger, S. E. (2006) Safety assessment of drug metabolites: characterization of chemically stable metabolites. Chem. Res. Toxicol. 19, 1564-1569.
    • (2006) Chem. Res. Toxicol , vol.19 , pp. 1564-1569
    • Humphreys, W.G.1    Unger, S.E.2
  • 12
    • 33845748169 scopus 로고    scopus 로고
    • Metabolites and safety: What are the concerns, and how should we address them?
    • Smith, D. A., and Obach, R. S. (2006) Metabolites and safety: what are the concerns, and how should we address them? Chem. Res. Toxicol. 19, 1570-1579.
    • (2006) Chem. Res. Toxicol , vol.19 , pp. 1570-1579
    • Smith, D.A.1    Obach, R.S.2
  • 13
    • 0019579579 scopus 로고
    • Autocatalytic alkylation of the cytochrome P-450 prosthetic heme group by 1-1- aminobenzotriazole. Isolation of an NN-bridged benzyne-protoporphyrin IX adduct
    • Ortiz de Montellano, P. R., and Mathews, J. M. (1981) Autocatalytic alkylation of the cytochrome P-450 prosthetic heme group by 1-1- aminobenzotriazole. Isolation of an NN-bridged benzyne-protoporphyrin IX adduct. Biochem. J. 195, 761-764.
    • (1981) Biochem. J , vol.195 , pp. 761-764
    • Ortiz de Montellano, P.R.1    Mathews, J.M.2
  • 14
    • 0001707017 scopus 로고
    • Cytochrome P-450 catalyzed oxidation of quadricyclane. Evidence for a radical cation intermediate
    • Stearns, R. A., and Ortiz de Montellano, P. R. (1985) Cytochrome P-450 catalyzed oxidation of quadricyclane. Evidence for a radical cation intermediate. J. Am. Chem. Soc. 107, 4081-4082.
    • (1985) J. Am. Chem. Soc , vol.107 , pp. 4081-4082
    • Stearns, R.A.1    Ortiz de Montellano, P.R.2
  • 15
    • 0035826779 scopus 로고    scopus 로고
    • The P450-1 gene of Gibberella fujikuroi encodes a multifunctional enzyme in gibberellin biosynthesis
    • Rojas, M. C., Hedden, P., Gaskin, P., and Tudzynski, B. (2001) The P450-1 gene of Gibberella fujikuroi encodes a multifunctional enzyme in gibberellin biosynthesis. Proc. Natl. Acad. Sci. U.S.A. 98, 5838-5843.
    • (2001) Proc. Natl. Acad. Sci. U.S.A , vol.98 , pp. 5838-5843
    • Rojas, M.C.1    Hedden, P.2    Gaskin, P.3    Tudzynski, B.4
  • 17
    • 2442509005 scopus 로고    scopus 로고
    • Conversion of the 2,2,6,6-tetramethylpiperidine moiety to a 2,2 dimethylpyrrolidine by cytochrome P450: Evidence for a mechanism involving nitroxide radicals and heme iron
    • Yin, W., Mitra, K., Stearns, R. A., Baillie, T. A., and Kumar, S. (2004) Conversion of the 2,2,6,6-tetramethylpiperidine moiety to a 2,2 dimethylpyrrolidine by cytochrome P450: evidence for a mechanism involving nitroxide radicals and heme iron. Biochemistry 43, 5455-5466.
    • (2004) Biochemistry , vol.43 , pp. 5455-5466
    • Yin, W.1    Mitra, K.2    Stearns, R.A.3    Baillie, T.A.4    Kumar, S.5
  • 18
    • 0033836982 scopus 로고    scopus 로고
    • Characterization of novel glutathione adducts of a non-nucleoside reverse transcriptase inhibitor, (S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-3,4-dihydro-2(1H) -quinazolinone (DPC 961), in rats. Possible formation of an oxirene metabolic intermediate from a disubstituted alkyne
    • Mutlib, A., Chen, H., Shockcor, J., Espina, R., Chen, S., Cao, K., Du, A., Nemeth, G., Prakash, S., and Gan, L.-S. (2000) Characterization of novel glutathione adducts of a non-nucleoside reverse transcriptase inhibitor, (S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-3,4-dihydro-2(1H) -quinazolinone (DPC 961), in rats. Possible formation of an oxirene metabolic intermediate from a disubstituted alkyne. Chem. Res. Toxicol. 13, 775-784.
    • (2000) Chem. Res. Toxicol , vol.13 , pp. 775-784
    • Mutlib, A.1    Chen, H.2    Shockcor, J.3    Espina, R.4    Chen, S.5    Cao, K.6    Du, A.7    Nemeth, G.8    Prakash, S.9    Gan, L.-S.10
  • 19
    • 0019977745 scopus 로고
    • Sulfation of minoxidil by liver sulfotransferase
    • Johnson, G. A., Barsuhn, K. J., and McCall, J. M. (1982) Sulfation of minoxidil by liver sulfotransferase. Biochem. Pharmacol. 31, 2949-2954.
    • (1982) Biochem. Pharmacol , vol.31 , pp. 2949-2954
    • Johnson, G.A.1    Barsuhn, K.J.2    McCall, J.M.3
  • 20
    • 0030004087 scopus 로고    scopus 로고
    • Peroxo-iron and oxenoid-iron species as alternative oxygenating agents in cytochrome P450-catalyzed reactions: Switching by threonine-302 to alanine mutagenesis of cytochrome P450 2B4
    • Vaz, A. D. N., Pernecky, S. J., Raner, G. M., and Coon, M. J. (1996) Peroxo-iron and oxenoid-iron species as alternative oxygenating agents in cytochrome P450-catalyzed reactions: switching by threonine-302 to alanine mutagenesis of cytochrome P450 2B4. Proc. Natl. Acad. Sci. U.S.A. 93, 4644-4648.
    • (1996) Proc. Natl. Acad. Sci. U.S.A , vol.93 , pp. 4644-4648
    • Vaz, A.D.N.1    Pernecky, S.J.2    Raner, G.M.3    Coon, M.J.4
  • 21
    • 0017358891 scopus 로고
    • Generation of reactive metabolites of N-hydroxy-phenacetin by glucoronidation and sulfation
    • Mulder, G. J., Hinson, J. A., and Gillette, J. R. (1977) Generation of reactive metabolites of N-hydroxy-phenacetin by glucoronidation and sulfation. Biochem. Pharmacol. 26, 189-196.
    • (1977) Biochem. Pharmacol , vol.26 , pp. 189-196
    • Mulder, G.J.1    Hinson, J.A.2    Gillette, J.R.3
  • 22
    • 0028816782 scopus 로고
    • Metabolic activation of the N-hydroxy derivative of the carcinogen 4-aminobiphenyl by human tissue sulfotransferases
    • Chou, H. C., Lang, N. P., and Kadlubar, F. F. (1995) Metabolic activation of the N-hydroxy derivative of the carcinogen 4-aminobiphenyl by human tissue sulfotransferases. Carcinogenesis 16, 413-417.
    • (1995) Carcinogenesis , vol.16 , pp. 413-417
    • Chou, H.C.1    Lang, N.P.2    Kadlubar, F.F.3
  • 23
    • 0020644885 scopus 로고
    • Sulfation and glucuronidation as competing pathways in the metabolism of hydroxamic acids: The role of N,O-sulfonation in chemical carcinogenesis of aromatic amines
    • Mulder, G. J., and Meerman, J. H. (1983) Sulfation and glucuronidation as competing pathways in the metabolism of hydroxamic acids: the role of N,O-sulfonation in chemical carcinogenesis of aromatic amines. Environ. Health Perspect 49, 27-32.
    • (1983) Environ. Health Perspect , vol.49 , pp. 27-32
    • Mulder, G.J.1    Meerman, J.H.2


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