Comparison of (S)-mephenytoin and proguanil oxidation in vitro: Contribution of several CYP isoforms

British Journal of Clinical Pharmacology

Volumn 48, Issue 2, 1999, Pages 158-167

  Coller, Janet K ^a   Somogyi, A A ^a   Bochner, F ^a  

^a UNIVERSITY OF ADELAIDE   (Australia)

Author keywords

(S) mephenytoin; CYP1A2; CYP2C19; CYP3 A4; Genotype; Human liver microsomes; Proguanil

Indexed keywords

CYCLOGUANIL; CYTOCHROME P450; DIAZEPAM; DIETHYLDITHIOCARBAMIC ACID; DRUG METABOLITE; DRUG METABOLIZING ENZYME; FURAFYLLINE; MEPHENYTOIN; OMEPRAZOLE; PROGUANIL; RESTRICTION ENDONUCLEASE; TROLEANDOMYCIN;

ARTICLE; CONTROLLED STUDY; DRUG CLEARANCE; DRUG METABOLISM; DRUG OXIDATION; DRUG SELECTIVITY; GENOTYPE; HUMAN; HUMAN TISSUE; IN VITRO STUDY; LIVER MICROSOME; MICHAELIS MENTEN KINETICS; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL;

ADULT; AGED; ANTIBODIES, MONOCLONAL; ANTICONVULSANTS; ANTIMETABOLITES; CHLOROGUANIDE; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; FEMALE; FOLIC ACID ANTAGONISTS; GENOTYPE; HUMANS; ISOENZYMES; MALE; MEPHENYTOIN; MICROSOMES, LIVER; MIDDLE AGED; OXIDATION-REDUCTION; TRIAZINES;

EID: 0032813511     PISSN: 03065251     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1365-2125.1999.00005.x     Document Type: Article

References (30)

1. 1 de Morais SMF, Wilkinson GR, Blaisdell J, Meyer UA, Nakamura K, Goldstein JA. Identification of a new genetic defect responsible for the polymorphism of S-mephenytoin metabolism in Japanese. Mol Pharmacol 1994; 46: 594-598.
2. 2 Reviriego J, Bertilsson L, Carrillo JA, Llerena A, Valdivielso MJ, Benitez J. Frequency of S-mephenytoin hydroxylation deficiency in 373 Spanish subjects compared to other Caucasian populations. Eur J Clin Pharmacol 1993; 44: 593-595.
3. 3 Nakamura K, Goto F, Ray WA, et al. Interethnic differences in genetic polymorphism of debrisoquin and mephenytoin hydroxylation between Japanese and Caucasian populations. Clin Pharmacol Ther 1985; 38: 402-408.
4. 4 Wilkinson GR, Guengerich FP, Branch RA. Genetic polymorphism of S-mephenytoin hydroxylation. Pharmacol Ther 1989; 43: 53-76.
5. 5 Kupfer A, Preisig R. Pharmacogenetics of mephenytoin: a new drug hydroxylation polymorphism in man. Eur J Clin Pharmacol 1984; 26: 753-759.
6. 6 de Morais SMF, Wilkinson GR, Blaisdell J, Nakamura K, Meyer UA, Goldstein JA. The major genetic defect responsible for the polymorphism of S-mephenytoin metabolism in humans. J Biol Chem 1994; 269: 15419-15422.
7. 7 Ferguson RJ, de Morais SMF, Benharnou S, et al. A new genetic defect in human CYP2C19: Mutation of the initiation codon is responsible for poor metabolism of S-mephenytoin. J Pharmacol Exp Ther 1998; 284: 356-361.
8. 8 Ibeanu GC, Blaisdell J, Ghanayem BI, et al. An additional defective allele CYP2C19*5, contributes to the S-mephenytoin poor metaboliser phenotype in Caucasians. Pharmacogenetics 1998; 8: 129-135.
9. 9 Ibeanu GC, Goldstein JA, Meyer U, et al. Identification of new human CYP2C19 alleles (CYP2C19*6 and CYP2C19*2B) in a Caucasian poor metaboliser of mephenytoin. J Pharmacol Exp Ther 1998; 286: 1490-1495.
10. 10 Birkett DJ, Rees D, Andersson T, Gonzalez FJ, Miners JO, Veronese ME. In vitro proguanil activation to cycloguanil by human liver microsomes is mediated by CYP3A isoforms as well as by S-mephenytoin hydroxylase. Br J Clin Pharmacol 1994; 37: 413-420.
11. 11 Helsby NA, Ward SA, Howells RE, Breckenridge AM. In vitro metabolism of the biguanide antimalarials in human liver microsomes: evidence for a role of the mephenytoin hydroxylase (P450MP) enzyme. Br J Clin Pharmacol 1990; 30: 287-291.
12. 12 Ward SA, Watkins WM, Mberu E, et al. Inter-subject variability in the metabolism of proguanil to the active metabolite cycloguanil in man. Br J Clin Pharmacol 1989; 27: 781-787.
13. 13 Edstein MD, Shanks GD, Teja-Isavadharm P, Rieckmann KH, Webster HK. Oxidative activation of proguanil and daspone acetytation in Thai soldiers. Br J Clin Pharmacol 1994; 37: 67-70.
14. 14 Meier UT, Dayer P, Male P-J, Kronbach T, Meyer UA. Mephenytoin hydroxylation polymorphism: Characterization of the enzymatic deficiency on liver microsomes of poor metabolizers phenotyped in vivo. Clin Pharmacol Ther 1985; 38: 488-494.
15. 15 Somogyi AA, Reinhard HA, Bochner F. Pharmacokinetic evaluation of proguanil: a probe phenotyping drug for the mephenytoin hydroxylase polymorphism. Br J Clin Pharmacol 1996; 41: 175-179.
16. 16 Coller JK, Somogyi AA, Bochner F. Association between CYP2C19 genotype and proguanil oxidative polymorphism. Br J Clin Pharmacol 1997; 43: 659-660.
17. 17 Hoskins JM, Shenfield GM, Gross AS. Relationship between proguanil metabolic ratio and CYP2C19 genotype in a Caucasian population. Br J Clin Pharmacol 1998; 46: 499-504.
18. 18 Zanger UM, Vilbois F, Hardwick JP, Meyer UA. Absence of hepatic cytochrome P450bufl causes genetically deficient debrisoquine oxidation in man. Biochemistry 1988; 27: 5447-5454.
19. 19 Lowry OH, Roseburg NJ, Farr AL, Randall RJ. Measurement with the folin phenol reagent. J Biol Chem 1951; 193: 265-275.
20. 20 Omura T, Sato R. The carbon monoxide-binding pigment of liver microsomes, II Solubilisation, purification and properties. J Biol Chem 1964; 234: 2374-2385.
21. 21 Newton DJ, Wang RW, Lu AYH. Cytochrome P450 inhibitors: Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metab Dispos 1995; 23: 154-158.
22. 22 Eagling VA, Tjia JF, Back DJ. Differential selectivity of cytochrome P450 inhibitors against probe substrates in human and rat liver microsomes. Br J Clin Pharmacol 1998; 45: 107-114.
23. 23 Andersson T, Miners JO, Veronese ME, Tassaneeyakul W, Meyer UA, Birkett DJ. Identification of human liver cytochrome P450 isoforms mediating omeprazole metabolism. Br J Clin Pharmacol 1993; 36: 521-530.
24. 24 Yasumori T, Qing Hua L, Yamazoe Y, Ueda M, Tsuzuki T, Kato R. Lack of low Km diazepam n demethylase in livers of poor metabolisers for S mephenytoin 4′-hydroxylation. Pharmacogenetics 1994; 4: 323-331.
25. 25 Kerry NL, Somogyi AA, Bochner F, Mikus G. The role of CYP2D6 in primary and secondary oxidative metabolism of dextromethorphan; in vitro studies using human liver microsomes. Br J Clin Pharmacol 1994; 38: 242-248.
26. 26 Jurima M, Inaba T, Kalow W. Mephenytoin metabolism in vitro by human liver. Drug Metab Dispos 1985; 13: 151-155.
27. 27 Hall SD, Guengerich FP, Branch RA, Wilkinson GR. Characterization and inhibition of mephenytoin 4-hydroxylase activity in human liver microsomes. J Pharmacol Exp Ther 1987; 240: 216-222.
28. 28 Chiba K, Saitoh A, Koyama F, Tani M, Hayashi M, Ishizaki T. The role of S-mephenytoin 4′-hydroxylase in imipramine metabolism by human liver microsomes: a two-enzyme kinetic analysis of N-demethylation and 2-hydroxylation. Br J Clin Pharmacol 1994; 37: 237-242.
29. 29 Halpert JR, Guengerich FP, Bend JR, Correia MA. Contemporary issues in toxicology: Selective inhibitors of cytochromes P450. Toxicol Appl Pharmacol 1994; 125: 163-175.
30. 30 Forrester LM, Henderson CJ, Glancey MJ, et al. Relative expression of cytochrome P450 isoenzymes in human liver and association with the metabolism of drugs and xenobiotics. Biochem J 1992; 281: 359-368.