Putative active site template model for cytochrome P4502C9 (tolbutamide hydroxylase)

Drug Metabolism and Disposition

Volumn 24, Issue 2, 1996, Pages 260-266

  Jones, B C ^a   Hawksworth, G ^b   Horne, V A ^a   Newlands, A ^b   Morsman, J ^b   Tute, M S ^a   Smith, D A ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

^b UNIVERSITY OF ABERDEEN   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 TERT BUTYLCYCLOHEXYL) 3 HYDROXY 1,4 NAPHTHOQUINONE; CYTOCHROME P450; DICLOFENAC; DRONABINOL; IBUPROFEN; NAPROXEN; NONSTEROID ANTIINFLAMMATORY AGENT; PHENYTOIN; SULFAPHENAZOLE; TOLBUTAMIDE; WARFARIN;

ARTICLE; DRUG METABOLISM; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME SPECIFICITY; ENZYME SUBSTRATE; HYDROGEN BOND; MOLECULAR MODEL; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

ARYL HYDROCARBON HYDROXYLASES; BINDING SITES; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN CONFORMATION; STEROID 16-ALPHA-HYDROXYLASE; STEROID HYDROXYLASES; SUBSTRATE SPECIFICITY; SULFAPHENAZOLE; TEMPLATES, GENETIC;

EID: 0030041933     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (13)

1. G. R. Strobl, S. von Kruedener, J. Stockigt, F. P. Guengerich, and T. Wolf: Development of a pharmacophore for inhibition of human liver cytochrome P4502D6: molecular modeling and inhibition studies. J Med. Chem. 36, 1136-1145 (1993).
2. D. A. Smith and B. C. Jones: Speculations on the substrate structureactivity relationship (SSAR) of cytochrome P450 enzymes. Biochem. Pharmacol. 44, 2089-2098 (1992).
3. C. J. Doecke, M. E. Veronese, S. M. Pond, J. O. Miners, D. J. Birkett, and M. E. McManus' Relationship between phenytoin and tolbutamide hydroxylations in human liver microsomes. Br. J. Clin. Pharmacol. 31, 125-130 (1991).
4. J. Zhao, T. Leemann, and P. Dayer In vitro oxidation of oxicam NSAIDS by a human liver cytochrome P450. Life Sci. 51, 575-581 (1992).
5. A. E. Rettie, R. K. Korzekwa, K. L. Kunze, R. F. Lawrence, A. C. Eddy, T. Aoyama, H. V. Gelboin, F. J. Gonzalez, and W. F. Trager: Hydroxylation of warfarin by human cDNA-expressed cytochrome P450: a role for P4502C9 in the etiology of (S)-warfarin-drug interactions. Chem Res. Toxicol. 5, 54-59 (1992).
6. R. J. Weaver, M. Dickins. and M. D. Burke: Cytochrome P4502C9 is responsible for the hydroxylation of the naphthoquinone antimalarial 58C80 in human liver. Biochem. Pharmacol. 46, 1183-1197 (1993)
7. L. M. Distlerath and F. P. Guengerich. Enzymology of human cytochromes P-450. In "Mammalian Cytochromes P450" (F. P. Guengerich. ed.), pp 134-188. CRC Press, Boca Raton, FL. 1987.
8. A. P. Koley, J. T. M. Butters. R C. Robinson, A. Markowitz, and F. K. Friedman: CO binding kinetics of human cytochrome P4503A4. J. Biol. Chem. 270, 5014-5018 (1995).
9. L. D. Heimark and W. F. Trager: The preferred solution conformation of warfarin at the active site of cytochrome P450 based on the CD spectra in octanol/water model system. J. Med. Chem. 27, 1092-1095 (1982).
10. D. A. Smith, B. C. Jones, and D. K. Walker: Design of drugs involving the concepts and theories of drug metabolism and pharmacokinetics. Med. Res. Rev. in press.
11. J. A Goldstein. M. B. Faletto, M. Romekes-Sparks, T. Sullivan, S. Kitareewan, J. L. Raucy, J. M. Lasker, and B. I. Ghanayem: Evidence that CYP2C19 is the major (S)-mephenytom 4′-hydroxylase in humans. Biochemistry 33, 1743-1752 (1994).
12. R. C. Wade: Solvation of the active site of cytochrome P450-cam J Comp.-Aided Mol. Des. 4, 199-204 (1990).
13. J. R. Cuppy-Vickery and T. L. Poulos: Structure of cytochrome P450eryF involved in erythromycin biosynthesis. Struct. Biol. 2, 144-152 (1995)