CYP3A4 and CYP3A5 catalyse the conversion of the N-methyl-D-aspartate (NMDA) antagonist CJ-036878 to two novel dimers

Xenobiotica

Volumn 37, Issue 12, 2007, Pages 1408-1420

  Emoto, C ^a   Nishida, H ^a   Hirai, H ^a   Iwasaki, K ^a,b  

^a PFIZER INC   (United States)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

CYP3A4; CYP3A5; Dimerization; Human liver microsomes

Indexed keywords

CJ 036878; CJ 047710; CJ 047713; CYTOCHROME P450; CYTOCHROME P450 3A4; CYTOCHROME P450 3A5; DRUG METABOLITE; KETOCONAZOLE; N (3 PHENETHOXYBENZYL) 4 HYDROXYBENZAMIDE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; PROADIFEN; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DIMERIZATION; DRUG CLEARANCE; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME MECHANISM; ENZYME METABOLISM; ENZYME SPECIFICITY; HUMAN; HUMAN CELL; LIVER MICROSOME; OXIDATION;

ADOLESCENT; ADULT; AGED; BENZAMIDES; CYTOCHROME P-450 CYP3A; DIMERIZATION; FEMALE; HUMANS; MALE; MICROSOMES, LIVER; MIDDLE AGED; OXIDATION-REDUCTION; RECEPTORS, N-METHYL-D-ASPARTATE;

EID: 36348973446     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.1080/00498250701658304     Document Type: Article

References (17)

1. Dansette PM, Bertho G, Mansuy D. 2005. First evidence that cytochrome P450 may catalyse both S-oxidation and epoxidation of thiophene derivatives. Biochemical and Biophysical Research Communications 338:450-455.
2. Emoto C, Iwasaki K. 2006. Enzymatic characteristics of CYP3A5 and CYP3A4: A comparison of in vitro kinetic and drug-drug interaction patterns. Xenobiotica 36:219-233.
3. Guengerich FP. 1995. Human cytochrome P450 enzymes. In: Oritiz de Montellano PR, editor. Cytochrome P450. New York, NY: Plenum. pp 473-535.
4. Guengerich FP. 1999. Cytochrome P-450 3A4: regulation and role in drug metabolism. Annual Reviews in Pharmacology and Toxicology 39:1-17.
5. Ha-Duong NT, Dijols S, Macherey AC, Goldstein JA, Dansette PM, Mansuy D. 2001. Ticlopidine as a selective mechanism-based inhibitor of human cytochrome P450 2C19. Biochemistry 40:12112-12122.
6. Houston JB, Kenworthy KE. 2000. In vitro-in vivo scaling of CYP kinetic data not consistent with the classical Michaelis-Menten model. Drug Metabolism and Disposition 28:246-254.
7. Isin EM, Guengerich FP. 2006. Complex reactions catalysed by cytochrome P450 enzymes. Biochimica et Biophysica Acta 1770:314-329.
8. Krishna DR, Klotz U. 1994. Extrahepatic metabolism of drugs in humans. Clinical Pharmacokinetics Concepts 26:144-160.
9. Lewis DF, Eddershaw PJ, Goldfarb PS, Tarbit MH. 1996. Molecular modelling of CYP3A4 from an alignment with CYP102: identification of key interactions between putative active site residues and CYP3A-specific chemicals. Xenobiotica 26:1067-1086.
10. Nelson DR, Koymans L, Kamataki T, Stegeman JJ, Feyereisen R, Waxman DJ, Waterman MR, Gotoh O, Coon MJ, Estabrook RW, et al. 1996. P450 superfamily: Update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics 6:1-42.
11. Rendic S. 2002. Summary of information on human CYP enzymes: Human P450 metabolism data. Drug Metabolism Reviews 34:83-448.
12. Shou M, Grogan J, Mancewicz JA, Krausz KW, Gonzalez FJ, Gelboin HV, Korzekwa KR. 1994. Activation of CYP3A4: Evidence for the simultaneous binding of two substrates in a cytochrome P450 active site. Biochemistry 33:6450-6455.
13. Spatzenegger M, Jaeger W. 1995. Clinical importance of hepatic cytochrome P450 in drug metabolism. Drug Metabolism Reviews 27:397-417.
14. Stadler R, Zenk MH. 1993. The purification and characterization of a unique cytochrome P-450 enzyme from Berberis stolonifera plant cell cultures. Journal of Biological Chemistry 268:823-831.
15. Suzuki H, Kneller MB, Haining RL, Trager WF, Rettie AE. 2002. (+)-N-3-benzyl-nirvanol and (-)-N-3-benzylphenobarbital: New potent and selective in vitro inhibitors of CYP2C19. Drug Metabolism and Disposition 30:235-239.
16. Zhao B, Guengerich FP, Bellamine A, Lamb DC, Izumikawa M, Lei L, Podust LM, Sundaramoorthy M, Kalaitzis JA, Reddy LM, et al. 2005. Binding of two flaviolin substrate molecules, oxidative coupling, and crystal structure of Streptomyces coelicolor A3(2) cytochrome P450 158A2. Journal of Biological Chemistry 280:11599-11607.
17. Zhuo M. 2002. Glutamate receptors and persistent pain: Targeting forebrain NR2B subunits. Drug Discovery Today 7:259-267.