Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 39, 2009 - Issue 2
292
Views
21
CrossRef citations to date
0
Altmetric
Research Article

Functional characterization of CYP3A4.16: Catalytic activities toward midazolam and carbamazepine

, , , , , , , , , & show all
Pages 140-147 | Received 04 Aug 2008, Accepted 11 Nov 2008, Published online: 01 Feb 2009

References

  • Dai D, Tang J, Rose R, Hodgson E, Bienstock RJ, Mohrenweiser HW,Goldstein JA. 2001. Identification of variants of CYP3A4 and characterization of their abilities to metabolize testosterone and chlorpyrifos. J Pharmacol Exp Ther 299:825–831.
  • Ekroos M, Sjögren T. 2006. Structural basis for ligand promiscuity in cytochrome P450 3A4. Proc Natl Acad Sci USA 103:13682–13687.
  • Fukushima-Uesaka H, Saito Y, Watanabe H, Shiseki K, Saeki M, Nakamura T, Kurose K, Sai K, Komamura K, Ueno K, Kamakura S, Kitakaze M, Hanai S, Nakajima T, Matsumoto K, Saito H, Goto Y, Kimura H, Katoh M, Sugai K, Minami N, Shirao K, Tamura T, Yamamoto N, Minami H, Ohtsu A, Yoshida T, Saijo N, Kitamura Y, Kamatani N, Ozawa S, Sawada J. 2004. Haplotypes of CYP3A4 and their close linkage with CYP3A5 haplotypes in a Japanese population. Hum Mutat 23:100.
  • Ghosal A, Satoh H, Thomas PE, Bush E, Moore D. 1996. Inhibition and kinetics of cytochrome P4503A activity in microsomes from rat, human, and cDNA-expressed human cytochrome P450. Drug Metab Dispos 24:940–947.
  • Guengerich FP. 1999. Cytochrome P-450 3A4: regulation and role in drug metabolism. Annu Rev Pharmacol Toxicol 39:1–17.
  • Hosea NA, Miller GP, Guengerich FP. 2000. Elucidation of distinct ligand binding sites for cytochrome P450 3A4. Biochemistry 39:5929–5939.
  • Hustert E, Haberl M, Burk O, Wolbold R, He YQ, Klein K, Nuessler AC, Neuhaus P, Klattig J, Eiselt R, Koch I, Zibat A, Brockmoller J, Halpert JR, Zanger UM, Wojnowski L. 2001. The genetic determinants of the CYP3A5 polymorphism. Pharmacogenetics 11:773–779.
  • Kerr BM, Thummel KE, Wurden CJ, Klein SM, Kroetz DL, Gonzalez FJ, Levy RH. 1994. Human liver carbamazepine metabolism. Role of CYP3A4 and CYP2C8 in 10,11-epoxide formation. Biochem Pharmacol 47:1969–1979.
  • Khan KK, He YQ, Domanski TL, Halpert JR. 2002. Midazolam oxidation by cytochrome P450 3A4 and active-site mutants: an evaluation of multiple binding sites and of the metabolic pathway that leads to enzyme inactivation. Mol Pharmacol 61:495–506.
  • Korzekwa KR, Krishnamachary N, Shou M, Ogai A, Parise RA, Rettie AE, Gonzalez FJ, Tracy TS. 1998. Evaluation of atypical cytochrome P450 kinetics with two-substrate models: evidence that multiple substrates can simultaneously bind to cytochrome P450 active sites. Biochemistry 37:4137–4147.
  • Lamba JK, Lin YS, Thummel K, Daly A, Watkins PB, Strom S, Zhang J, Schuetz EG. 2002. Common allelic variants of cytochrome P4503A4 and their prevalence in different populations. Pharmacogenetics 12:121–132.
  • Lee SJ, Bell DA, Coulter SJ, Ghanayem B, Goldstein JA. 2005. Recombinant CYP3A4*17 is defective in metabolizing the hypertensive drug nifedipine, and the CYP3A4*17 allele may occur on the same chromosome as CYP3A5*3, representing a new putative defective CYP3A haplotype. J Pharmacol Exp Ther 313:302–309.
  • Lee SJ, Lee SS, Jeong HE, Shon JH, Ryu JY, Sunwoo YE, Liu KH, Kang W, Park YJ, Shin CM, Shin JG. 2007. The CYP3A4*18 allele, the most frequent coding variant in Asian populations, does not significantly affect the midazolam disposition in heterozygous individuals. Drug Metab Dispos 35:2095–2101.
  • Murayama N, Nakamura T, Saeki M, Soyama A, Saito Y, Sai K, Ishida S, Nakajima O, Itoda M, Ohno Y, Ozawa S, Sawada J. 2002. CYP3A4 gene polymorphisms influence testosterone 6beta-hydroxylation. Drug Metab Pharmacokinet 17:150–156.
  • Nakajima Y, Yoshitani T, Fukushima-Uesaka H, Saito Y, Kaniwa N, Kurose K, Ozawa S, Aoyagi N, Kamatani N, Yamamoto N, Kunitoh H, Ohe Y, Tamura T, Yoshida T, Minami H, Saijo N, Katori N, Sawada J. 2006. Impact of the haplotype CYP3A4*16B harboring the Thr185Ser substitution on paclitaxel metabolism in Japanese patients with cancer. Clin Pharmacol Ther 80:179–191.
  • Nakamura H, Torimoto N, Ishii I, Ariyoshi N, Nakasa H, Ohmori S, Kitada M. 2003. CYP3A4 and CYP3A7-mediated carbamazepine 10,11-epoxidation are activated by differential endogenous steroids. Drug Metab Dispos 31:432–438.
  • Omura T, Sato R. 1964. The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239:2370–2378.
  • Ozdemir V, Kalow W, Tang BK, Paterson AD, Walker SE, Endrenyi L, Kashuba AD. 2000. Evaluation of the genetic component of variability in CYP3A4 activity: a repeated drug administration method. Pharmacogenetics 10:373–388.
  • Phillips AH, Langdon RG. 1962. Hepatic triphosphopyridine nucleotide-cytochrome c reductase: isolation, characterization, and kinetic studies. J Biol Chem 237:2652–2660.
  • Sai K, Saito Y, Fukushima-Uesaka H, Kurose K, Kaniwa N, Kamatani N, Shirao K, Yamamoto N, Hamaguchi T, Kunitoh H, Ohe Y, Tamura T, Yamada Y, Minami H, Ohtsu A, Yoshida T, Saijo N, Sawada J. 2008. Impact of CYP3A4 haplotypes on irinotecan pharmacokinetics in Japanese cancer patients. Cancer Chemother Pharmacol 62:529–537.
  • Saito Y, Maekawa K, Ozawa S, Sawada J. 2007. Genetic polymorphisms and haplotypes of major drug metabolizing enzymes in Asians and their comparison with other ethnic populations. Curr Pharmacogenomics 5:49–78.
  • Sata F, Sapone A, Elizondo G, Stocker P, Miller VP, Zheng W, Raunio H, Crespi CL, Gonzalez FJ. 2000. CYP3A4 allelic variants with amino acid substitutions in exons 7 and 12: evidence for an allelic variant with altered catalytic activity. Clin Pharmacol Ther 67:48–56.
  • Shimada T, Yamazaki H, Mimura M, Inui Y, Guengerich FP. 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. J Pharmacol Exp Ther 270:414–423.
  • Shou M, Lin Y, Lu P, Tang C, Mei Q, Cui D, Tang W, Ngui JS, Lin CC, Singh R, Wong BK, Yergey JA, Lin JH, Pearson PG, Baillie TA, Rodrigues AD, Rushmore TH. 2001. Enzyme kinetics of cytochrome P450-mediated reactions. Curr Drug Metab 2:17–36.
  • Thummel KE, Wilkinson GR. 1998. In vitro and in vivo drug interactions involving human CYP3A. Annu Rev Pharmacol Toxicol 38:389–430.
  • Williams PA, Cosme J, Vinkovic DM, Ward A, Angove HC, Day PJ, Vonrhein C, Tickle IJ, Jhoti H. 2004. Crystal structures of human cytochrome P450 3A4 bound to metyrapone and progesterone. Science 305:683–686.
  • Yamaoka K, Tanaka H, Okumura K, Yasuhara M, Hori R. 1986. An analysis program MULTI(ELS) based on extended nonlinear least squares method for microcomputers. J Pharmacobiodyn 9:161–173.
  • Yamazaki H, Nakajima M, Nakamura M, Asahi S, Shimada N,Gillam EM, Guengerich FP, Shimada T, Yokoi T. 1999. Enhancement of cytochrome P-450 3A4 catalytic activities by cytochrome b(5) in bacterial membranes. Drug Metab Dispos 27:999–1004.
  • Yano JK, Wester MR, Schoch GA, Griffin KJ, Stout CD, Johnson EF. 2004. The structure of human microsomal cytochrome P450 3A4 determined by X-ray crystallography to 2.05-å resolution. J Biol Chem 279:38091–38094.
  • Yin T, Maekawa K, Kamide K, Saito Y, Hanada H, Miyashita K, Kokubo Y, Akaiwa Y, Otsubo R, Nagatsuka K, Otsuki T, Horio T, Takiuchi S, Kawano Y, Minematsu K, Naritomi H, Tomoike H, Sawada J, Miyata T. 2008. Genetic variations of CYP2C9 in 724 Japanese individuals and their impact on the antihypertensive effects of losartan. Hypertens Res 31:1549–1557.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.