Contribution of human hepatic cytochrome P450s and steroidogenic CYP17 to the N-demethylation of aminopyrine

References

• AGUNDEZ, J. A. G., CARRILLO, J. A., MARTINES, C. and BENIDEZ, J., 1995a, Aminopyrine metabolism in man: the acetylation of aminoantipyrine cosegregates with acetylation of caffeine. Therapeutic Drug Monitoring, 17, 1–5.
   Google Scholar
• AGUNDEZ, J. A. G., MARTINES, C. and BENIDEZ, J., 1995b, Metabolism of aminopyrine and derivatives in man: in vivo study of monomorphic and polymorphic metabolic pathway. Xenobiotica, 25, 417–427.
   Google Scholar
• AOYAMA, T., KORZEKWA, K., NAGATA, K., GILLETTE, J., GELBOIN, H. V. and GONZALEZ, F. J., 1990, Estradiol metabolism by complementary deoxyribonucleic acid-expressed human cytochrome P450s. Endocrinology, 126, 3101–3106.
   PubMed Web of Science ®Google Scholar
• FUNAE, Y. and IMAOKA, S., 1993, Cytochrome P450 in rodents. In J. B. Schenkman and H. Greim (eds), Cytochrome P450 (Berlin: Springer), pp. 221–238.
   Google Scholar
• GARCIA-AGUNDEZ, J. A. G., LUANG°, A., BENITEZ, J. and BENIDEZ, J., 1990, Aminopyrine N-demethylase activity in human liver microsomes. Clinical and Pharmacological Therapeutics, 48, 490–495. GUENGERICH, F. P., 1992, Characterization of human cytochrome P450 enzymes. F ASEB Journal, 6, 745–748.
   Google Scholar
• GUENGERICH, F. P., 1996, In vitro techniques for studying drug metabolism. Journal of Pharmacohinetics and Biopharmaceutics, 24, 521–533.
   PubMed Web of Science ®Google Scholar
• GUENGERICH, F. P., GILLAM, M. J. and SHEVIADA, T., 1996, New applications of bacterial systems to problems in toxicology. Critical Review in Toxicology, 26, 551–583.
   PubMed Web of Science ®Google Scholar
• Imm, T., GLOBERMAN, H., GERTNER, J. M., KAGAWA, N. and WATERMAN, M. R., 1993, Expression and purification of functional human 17a-hydroxylase/17,20-lyase (P450c17) in Escherkhia coli: use of this system for study of a novel form of combined 17a-hydroxylase/17,20-lyase deficiency. Journal of Biological Chemistry, 268, 10681–10689.
   PubMed Web of Science ®Google Scholar
• IMAOKA, S., YAMADA, T., HIROI, T., HAYASHI, K., SAKAKI, T., YABUSAKI, Y. and FUNAE, Y., 1996, Multiple forms of human P450 expressed in Saccharomyces cerevisiae. Biochemical Pharmacology, 51, 1041–1050.
   PubMed Web of Science ®Google Scholar
• INOUE, K., YAMAZAKI, H., ImIYA, K., AKASAKA, S., GUENGERICH, F. P. and SHLMADA, T., 1997, Relationship between CYP2C9 and CYP2C19 genotypes and tolbutamide methyl hydroxylation and S-mephenytoin 4'-hydroxylation activities in livers of Japanese and Caucasian populations. Pharmacogenetks, 7, 103–113.
   PubMedGoogle Scholar
• KAGAWA, N. and WATERMAN, M. R., 1995, Regulation of steroidogenic and related P450s. In P. R. Ortiz de Montellano (ed.), Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd edn (New York: Plenum), pp. 419–442.
   Google Scholar
• KATAGIRI, M., KAGAWA, N. and WATERMAN, M. R., 1995, The role of cytochrome b., in the biosynthesis of androgens by human P450c17. Archives of Biochemistry and Biophysics, 317, 343-347. KOMORI, M., HASHIZUME, T., OHI, H., MIURA, T., KITADA, M., NASHIMA, K. and KAMATAKI, T., 1988, Cytochrome P-450 in human liver microsomes: high-performance liquid chromatographic isolation of three forms and their characterization. Journal of Biochemistry, 104, 912-916. MOFFAT, J., 1986, Dypirone-containing analgesica. South African Medical Journal, 70, 331–332.
   Google Scholar
• NASH, T., 1953, The colorimetric estimation of formaldehyde by means of the Hantzsch reaction. Biochemical Journal, 55, 416–421.
   PubMed Web of Science ®Google Scholar
• NIWA, T., NARITOMI, Y., KAWANO M., UEDA - SHLMOHIRA, Y., TAICESHITA, K., SHIRAGA, T., IWASAKI, K. and NODA, K., 1994, Effect of repeated injection of somatomedin C on drug metabolizing enzyme activities in rats. Research Communications in Chemical Pathology and Pharmacology, 83, 341–348.
   Google Scholar
• NIWA, T., YABUSAKI, Y., HONMA, K., MATSUO, N., TATSUTA, K., ISHIBASHI, F. and KATAGIRI, M., 1998, Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica, 28, 539–547.
   PubMed Web of Science ®Google Scholar
• NORKUS, E. P. and KUENZIG, W. A., 1985, Studies on the antimutagenic activity of ascorbic acid in vitro and in vivo. Carcinogenesis, 6, 1593–1598.
   PubMed Web of Science ®Google Scholar
• OMURA, T. and SATO, R., 1964, The carbon monoxide-binding pigment of liver microsomes. Journal of Biological Chemistry, 239, 2370–2378.
   PubMed Web of Science ®Google Scholar
• PISCIOTTA, A. V., 1990, Drug-induced agranulocytosis. Peripheral destruction of polymorphonuclear leucocytes and their marrow precursors. Blood Reviews, 4, 226–237.
   PubMed Web of Science ®Google Scholar
• SHIMADA, T., YAMAZAKI, H., MIMURA, M., INUI, Y. and GUENGERICH, F. P., 1994, Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. Journal of Pharmacology and Experimental Therapeutics, 270, 414–423.
   PubMed Web of Science ®Google Scholar
• SHIRAGA, T., IWASAKI, K., NoZAKI, K., TAMURA, T., YAMAZOE, Y., KATO, R. and TAKANAK A., 1994, Isolation and characterization of four cytochrome P450 isozymes from untreated and pheno-barbital-treated beagle dogs. Biological and Pharmaceutical Bulletin, 17, 22–28.
   PubMed Web of Science ®Google Scholar
• VoLz, M. and KELLNER, H.-M., 1980, Kinetics and metabolism of pyrazolones (propyphenazone, aminopyrine, and dipyrone). British Journal of Clinical Pharmacology, 10, 299S–308S.
   Google Scholar
• WILKINSON, G. R., GUENGERICH, F. P. and BRANCH, R. A. 1989, Genetic polymorphism of S-mephenytoin hydroxylation. Pharmacology and Therapeutics, 43, 53–76.
   PubMed Web of Science ®Google Scholar