The development of drug metabolism research as expressed in the publications of ASPET: Part 2, 1959-1983

Drug Metabolism and Disposition

Volumn 36, Issue 6, 2008, Pages 981-985

  Murphy, Patrick J ^a,b  

^a BUTLER UNIVERSITY   (United States)

^b NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

16ALPHA CYANOPREGNENOLONE; BETA NAPHTHOFLAVONE; CYTOCHROME P450; CYTOCHROME P450 INHIBITOR; GLYCOPROTEIN P; PARACETAMOL; PHENOBARBITAL; PHENYTOIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

BIOTRANSFORMATION; DRUG DISPOSITION; DRUG METABOLISM; DRUG RESEARCH; ENZYME ACTIVITY; ENZYME INDUCTION; GENETIC POLYMORPHISM; HEALTH CARE ORGANIZATION; HUMAN; LIVER MICROSOME; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION; PUBLICATION; REVIEW;

ANIMALS; BIOMEDICAL RESEARCH; BIOTRANSFORMATION; CYTOCHROME P-450 ENZYME SYSTEM; HISTORY, 20TH CENTURY; HUMANS; PHARMACEUTICAL PREPARATIONS; PHARMACOKINETICS; PUBLICATIONS; SOCIETIES, SCIENTIFIC;

EID: 44149113782     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.021113     Document Type: Review

References (84)

1. Allen JG, East PB, Francis RJ, and Haigh JL (1975) Metabolism of debrisoquine sulfate: identification of some urinary metabolites in rat and man. Drug Metab Dispos 3:332-337.
2. Alvares AP, Schilling G, Levin W, and Kuntzman R (1968) Alteration of the microsomal hemoprotein by 3-methylcholanthrene; effects of ethionine and actinomycin D. J Pharmacol Exp Ther 163:417-424.
3. Atkinson AJ Jr, MacGee J, Strong J, Garteiz D, and Gaffney TE (1970) Identification of 5-meta-hydroxyphenyl-5-phenylhydantoin as a metabolite of diphenylhydantoin. Biochem Pharmacol 19:2483-2491.
4. Baumann E and Preuss C (1879) Ueber Bromphenylmercaptursaure. Ber deut chem Ges 12:806-810.
5. Boobis AR, Murray S, Kahn GC, Robertz GM, and Davies DS (1983) Substrate specificity of the form of cytochrome P-450 catalyzing the 4-hydroxylation of debrisoquine in man. Mol Pharmacol 23:474-481.
6. Bray HG, Franklin TJ, and James SP (1959a) The formation of mercapturic acids. 2. The possible role of glutathionase. Biochem J 71:690-696.
7. Bray HG, Franklin TJ, and James SP (1959b) The formation of mercapturic acids. 3. N-acetylation of S-substituted cysteines in the rabbit, rat and guinea pig. Biochem J 73:465-473.
8. Bresnick E, Foldes R, and Hines RN (1984) Induction of cytochrome P450 by xenobiotics. Pharmacol Rev 36:43S-51S.
9. Buening MK, Wislocki PG, Levin W, Yagi H, Thakker DR, Akagi H, Koreeda M, Jerina DM, Conney AH (1978) Tumorigenicity of the optical enantiomers of the diastereomeric benzo-[a]pyrene 7,8-diol-9,10-epoxides in newborn mice: exceptional activity of (+)-7beta,8alpha-dihydroxy-9alpha,10alpha-epoxy-7,8,9, 10-tetrahydrobenzo[a]pyrene. Proc Natl Acad Sci U S A 75:5358-5361.
10. Butler TC (1957) The metabolic conversion of 5,5-diphenyl hydantoin to 5-(p-hydroxyphenyl)-5-phenyl hydantoin. J Pharmacol Exp Ther 119:1-11.
11. Chang T, Savory A, and Glazko AJ (1970) A new metabolite of 5,5-diphenylhydantoin (Dilantin). Biochem Biophys Res Commun 38:444-449.
12. Conney AH (1967) Pharmacological implications of microsomal enzyme induction. Pharmacol Rev 19:317-366.
13. Conney AH, Davis C, Gastel R, and Burns JJ (1960) Adaptive increases in drug-metabolizing enzymes induced by phenobarbital and other drugs. J Pharmacol Exp Ther 130:1-8.
14. Conney AH, Lu AYH, Levin W, Somogyi A, West S, Jacobson M, Ryan D, and Kuntzman R (1973) Effect of enzyme inducers on substrate specificity of the cytochromes P-450's. Drug Metab Dispos 1:199-210.
15. Conney AH, Miller EC, and Miller JA (1956) The metabolism of methylated aminoazo dyes. V. Evidence for induction of enzyme synthesis in the rat by 3-methylcholanthrene. Cancer Res 16:450-459.
16. Coon M (1981) The 1980 Bernard B. Brodie award lecture. Drug metabolism by cytochrome P-450: progress and perspectives. Drug Metab Dispos 9:1-4.
17. Cooper DY (1973) Discovery of the function of the heme protein P-450: a systematic approach to scientific research. Life Sci 13:1151-1161.
18. Cooper DY, Estabrook RW, and Rosenthal O (1963) The stoichiometry of C21 hydroxylation of steroids by adrenocortical microsomes. J Biol Chem 238:1320-1323.
19. Cooper DY, Levin S, Narasimhulu S, Rosenthal O, and Estabrook RW (1965) Photochemical action spectrum of the terminal oxidase of mixed function oxidase systems. Science 147:400-402.
20. Davies DS, Kahn GC, Murray S, Brodie MJ, and Boobis AR (1981) Evidence for an enzymatic defect in the 4-hydroxylation of debrisoquine by human liver. Br J Clin Pharmacol 11:89-91.
21. De Matteis F (1971) Loss of haem in rat liver caused by the porphyrogenic agent 2-allyl-2-isopropylacetamide. Biochem J 124:767-777.
22. Distlerath LM and Guengerich FP (1984) Characterization of a human liver cytochrome P-450 involved in the oxidation of debrisoquine and other drugs by using antibodies raised to the analogous rat enzyme. Proc Natl Acad Sci U S A 81:7348-7352.
23. Eichelbaum M, N Spannbrucker, and HJ Dengler (1978) A probably genetic defect of the metabolism of sparteine, in Biological Oxidation of Nitrogen (Gorrod JW, ed) pp 113-118, Elsevier/North Holland Biomedical Press, Amsterdam.
24. Elshourbagy NA and Guzelian PS (1980) Separation, purification, and characterization of a novel form of hepatic cytochrome P-450 from rats treated with pregnenolone-16 alpha-carbonitrile. J Biol Chem 255:1279- 1285.
25. Estabrook RW (2003) A passion for P450s (remembrances of the early history of research on Cytochrome P450). Drug Metab Dispos 31:1461-1473.
26. Estabrook RW, Cooper DY, and Rosenthal O (1963) The light-reversible carbon monoxide inhibition of the steroid C-21 hydroxylation system of the adrenal cortex. Biochem Z 338:741-755.
27. Fujii-Kuriyama Y, Mizukami Y, Kawajiri K, Sogawa K, and Muramatsu M (1982) Primary structure of a cytochrome P-450: coding nucleotide sequence of phenobarbital-inducible cytochrome P-450 cDNA from rat liver. Proc Natl Acad Sci U S A 79:2793-2797.
28. Gillette J, Sasame H, and Stripp B (1973) Mechanisms of inhibition of drug metabolic reactions. Drug Metab Dispos 1:164-175.
29. Guengerich FP, Dannan GA, Wright ST, Martin MV, Kaminsky LS (1982) Purification and characterization of liver microsomal cytochromes p-450: electrophoretic, spectral, catalytic, and immunochemical properties and inducibility of eight isozymes isolated from rats treated with phenobarbital or beta-naphthoflavone. Biochemistry 21:6019-6030.
30. Guroff G, Daly JW, Jerina DM, Renson J, Witkop B, Udenfriend S (1967) Hydroxylation-induced migration: the NIH shift. Recent experiments reveal an unexpected and general result of enzymatic hydroxylation of aromatic compounds. Science 157:1524-1530.
31. Hayaishi O (1962) History and scope, in Oxygenases, pp 1-29, Academic Press, New York.
32. Hinson JA, Monks TJ, Hong M, Highet RJ, and Pohl LR (1982) 3-(Glutathion-Syl) acetaminophen: a biliary metabolite of acetaminophen. Drug Metab Dispos 10:47-50.
33. Imai Y and Sato R (1966) Evidence for two forms of P-450 hemoprotein in microsomal membranes. Biochem Biophys Res Commun 23:5-11.
34. Jerina DM (1983) The 1982 Bernard B. Brodie award lecture. Metabolism of aromatic hydrocarbons by the cytochrome P-450 system and epoxide hydrolase. Drug Metab Dispos 11:1-4.
35. Jerina DM and Daly JW (1974) Arene oxides: a new aspect of drug metabolism. Science 185:573-582.
36. Jollow DJ, Mitchell JR, Potter WZ, Davis DC, Gillette JR, and Brodie BB (1973) Acetaminophen-induced hepatic necrosis. II. Role of covalent binding in vivo. J Pharmacol Exp Ther 187:195-202.
37. Juliano RL and Ling V (1976) A surface glycoprotein modulating drug permeability in Chinese hamster ovary cell mutants. Biochim Biophys Acta 455:152-162.
38. Kaminsky LS, Dunbar DA, Wang PP, Beaune P, Larrey D, Guengerich FP, Schnellmann RG, and Sipes IG (1984) Human hepatic cytochrome P-450 composition as probed by in vitro microsomal metabolism of warfarin. Drug Metab Dispos 12:470-477.
39. Katagiri M, Ganguli BN, Gunsalus IC (1968) A soluble cytochrome P-450 functional in methylene hydroxylation. J Biol Chem 243:3543-3546.
40. Kumaki K, Sato M, Kon H, and Nebert DW (1978) Correlation of type I, type II, and reverse type I difference spectra with absolute changes in spin state of hepatic microsomal cytochrome P-450 iron from five mammalian species. J Biol Chem 253:1048-1058.
41. Levin W (1990) The 1988 Bernard B. Brodie award lecture. Functional diversity of hepatic cytochromes P450. Drug Metab Dispos 18:824-830.
42. Lieber CS and DeCarli LM (1970) Hepatic microsomal ethanol-oxidizing system. In vitro characteristics and adaptive properties in vivo. J Biol Chem 245:2505-2512.
43. Lieber CS and DeCarli LM (1972) The role of the hepatic microsomal ethanol oxidizing system (MEOS) for ethanol metabolism in vivo. J Pharmacol Exp Ther 181:279-287.
44. Lieber CS and DeCarli LM (1973) The significance and characterization of hepatic microsomal ethanol oxidation in the liver. Drug Metab Dispos 1:428-440.
45. Lipscomb JD and Gunsalus IC (1973) Structural aspects of the active site of cytochrome P-450cam. Drug Metab Dispos 1:1-5.
46. Lu AY and West SB (1979) Multiplicity of mammalian microsomal cytochromes P-450. Pharmacol Rev 31:277-295.
47. Lu AY (1998) The 1996 Bernard B. Brodie lecture. A journey in cytochrome P450 and drug metabolism research. Drug Metab Dispos 26:1168-1173.
48. Lu AY, Coon MJ (1968) Role of hemoprotein P450 in fatty acid ω-hydroxylation in a soluble enzyme system from liver microsomes. J Biol Chem 243:1331-1332.
49. Lu AY, Kuntzman R, West S, Jacobson M, Conney AH (1972) Reconstituted liver microsomal enzyme system that hydroxylates drugs, other foreign compounds, and endogenous substrates. II. Role of the cytochrome P-450 and P-448 fractions in drug and steroid hydroxylations. J Biol Chem 247:1727-1734.
50. Lu AYH, Levin W, West SB, Jacobson M, Ryan D, Kuntzman R, and Conney AH (1973) Reconstituted liver microsomal enzyme system that hydroxylates drugs, other foreign compounds, and endogenous substrates. VI. Different substrate specificities of the cytochrome P450 fractions from control and phenobarbital-treated rats. J Biol Chem 248:456-460.
51. Machinist JM, Dehner EW, and Ziegler DM (1968) Microsomal oxidases. 3. Comparison of species and organ distribution of dialkylarylamine N-oxide dealkylase and dialkylarylamine N-oxidase. Arch Biochem Biophys 125:858-864.
52. Maguire JH, Butler TC, and Dudley KH (1980) Absolute configurations of the dihydrodiol metabolites of 5,5-diphenylhydantoin (phenytoin) from rat, dog, and human urine. Drug Metab Dispos 8:325-331.
53. Mahgoub A, Idle JR, Dring LG, Lancaster R, and Smith RL (1977) Polymorphic hydroxylation of debrisoquine in man. Lancet 2:584-586.
54. Mannering GJ (1986) The 1984 Bernard B. Brodie award lecture. From morphine to interferon: an odyssey of drug metabolism. Drug Metab Dispos 14:1-4.
55. Mason H (1957) Mechanisms of oxygen metabolism. Adv Enzymol Relat Subj Biochem 19:79-233.
56. Masters BS and Ziegler DM (1971) The distinct nature and function of NADPH-cytochrome c reductase and the NADPH-dependent mixed-function amine oxidase of porcine liver microsomes. Arch Biochem Biophys 145:358-364.
57. Maynert EW (1960) The metabolic fate of diphenylhydantoin in the dog, rat and man. J Pharmacol Exp Ther 130:275-284.
58. Mellström B, Bertilsson L, Birgersson C, Goransson M, and von Bahr C (1983) E- and Z-10-hydroxylation of nortriptyline by human liver microsomes - methods and characterization. Drug Metab Dispos 11:115-119.
59. Mitchell JR, Jollow DJ, Potter WZ, Davis DC, Gillette JR, and Brodie BB (1973a) Acetaminophen-induced hepatic necrosis. I. Role of drug metabolism. J Pharmacol Exp Ther 187:185-194.
60. Mitchell JR, Jollow DJ, Potter WZ, Gillette JR, and Brodie BB (1973b) Acetaminophen-induced hepatic necrosis. IV. Protective role of glutathioone. J Pharmacol Exp Ther 187:211-217.
61. Moustafa MA, Claesen M, Adline J, Vandervorst D, Poupaert JH (1983) Evidence for an arene-3,4-oxide as a metabolic intermediate in the meta- and para-hydroxylation of phenytoin in the dog. Drug Metab Dispos 11:574-580.
62. Murphy PJ (2008) The development of drug metabolism research as expressed in the publications of ASPET: part 1, 1909-1958. Drug Metab Dispos 36:1-5.
63. Ohnishi K and Lieber CS (1977) Reconstitution of the microsomal ethanol-oxidizing system. Qualitative and quantitative changes of cytochrome P-450 after chronic ethanol consumption. J Biol Chem 252:7124- 7131.
64. Omura T and Sato R (1962) A new cytochrome in liver microsomes. J Biol Chem 237:1375-1376.
65. Ortiz de Montellano PR (1995) The 1994 Bernard B Brodie award lecture: Structure, Mechanism, and inhibition of Cytochrome P-450. Drug Metab Dispos 23:1181-1187.
66. Ortiz de Montellano PR and Correia MA (1983) Suicidal destruction of cytochrome P-450 during oxidative drug metabolism. Annu Rev Pharmacol Toxicol 23:481-503.
67. Ortiz de Montellano PR and Mathews JM (1981) Autocatalytic alkylation of the cytochrome P-450 prosthetic haem group by 1-aminobenzotriazole. Biochem J 195:761-764.
68. Ortiz de Montellano PR and Mico BA (1980) Destruction of cytochrome P-450 by ethylene and other olefins. Mol Pharmacol 18:128-135.
69. Palade GE and Siekkevitz P (1956) Liver microsomes; an integrated morphological and biochemical study. J Biophys Biochem Cytol 2:171-200.
70. Poland A, Glover E, and Kende AS (1976) Stereospecific, high affinity binding of 2,3,7,8-tetrachlorodibenzo-p-dioxin by hepatic cytosol. Evidence that the binding species is receptor for induction of aryl hydrocarbon hydroxylase. J Biol Chem 251:4936-4946.
71. Potter WZ, Davis DC, Mitchell JR, Jollow DJ, Gillette JR, and Brodie BB (1973) Acetaminophen-induced hepatic necrosis. III. Cytochrome P-450-mediated covalent binding in vitro. J Pharmacol Exp Ther 187:203-210.
72. Remmer H and Merker HJ (1963) Drug-induced changes in the liver endoplasmic reticulum: association with drug-metabolizing enzymes. Science 142:1657-1658.
73. Remmer H, Schenkman J, Estabrook RW, Sasame H, Gillette J, Narasimhulu S, Cooper DY, and Rosenthal O (1966) Drug interaction with hepatic microsomal cytochrome. Mol Pharmacol 2:187-190.
74. Riordan JR and Ling V (1979) Purification of P-glycoprotein from plasma membrane vesicles of Chinese hamster ovary cell mutants with reduced colchicine permeability. J Biol Chem 254:12701-12705.
75. Rubin E and Lieber CS (1968) Hepatic microsomal enzymes in man and rat: induction and inhibition by ethanol. Science 162:690-691.
76. Ryan KJ and Engel LL (1957) Hydroxylation of steroids at carbon 21. J Biol Chem 225:103-114.
77. Schenkman JB, Remmer H, and Estabrook RW (1967) Spectral studies of drug interaction with hepatic microsomal cytochrome. Mol Pharmacol 3:113-123.
78. Sladek NE and Mannering GJ (1966) Evidence for a new P-450 hemoprotein in hepatic microsomes from methylcholanthrene-treated rats. Biochem Biophys Res Commun 22:668-674.
79. Thomas PE, Lu AYH, Ryan D, West SB, Kawalek J, and Levin W (1976) Immunochemical evidence for six forms of rat liver cytochrome P-450 using antibodies against purified rat liver cytochromes P-450 and P-448. Mol Pharmacol 12:746-758.
80. van Bladeren PJ, Breimer DD, Seghers CJ, Vermeulen NP, van der Gen A, and Cauvet J (1981) Dose-dependent stereoselectivity in the formation of mercapturic acids from cyclohexene oxide by the rat. Drug Metab Dispos 9:207-211.
81. Wang PP BP, Kaminsky LS, Dannan GA, Kadlubar FF, Larrey D, and Guengerich FP (1983) Purification and characterization of six cytochrome P-450 isozymes from human liver microsomes. Biochemistry 22:5375-5383.
82. Wang T, Roden DM, Wolfenden HT, Woosley RL, Wood AJ, and Wilkinson GR (1984) Influence of genetic polymorphism on the metabolism and disposition of encainide in man. J Pharmacol Exp Ther 228:605-611.
83. Ziegler DM (1991) The 1990 Bernard B. Brodie award lecture. Unique properties of the enzymes of detoxication. Drug Metab Dispos 19:847-852.
84. Ziegler DM and Gold MS (1971) Oxidative metabolism of tertiary amine drugs by human liver tissue. Xenobiotica 1:325-326.