Influence of the genetic polymorphisms in the 5′ flanking and exonic regions of CYP2C19 on proguanil oxidation

Drug Metabolism and Pharmacokinetics

Volumn 24, Issue 6, 2009, Pages 537-548

  Chakradhara, Rao Uppugunduri Satyanarayana ^a   Anichavezhi, Devendran ^a   Muthukumaran, Jayaraman ^b   Jayakanthan, Mannu ^b   Premendu, P Mathur ^b   Shewade, Gopal Deepak ^a   Krishnamoorthy, Rajagopal ^c   Adithan, Chandrasekaran ^a  

^a JAWAHARLAL INSTITUTE OF POSTGRADUATE MEDICAL EDUCATION AND RESEARCH   (India)

^b PONDICHERRY UNIVERSITY   (India)

^c HÔPITAL ROBERT DEBRÉ   (France)

Author keywords

CYP2C19; Docking; Phenotype; Promoter; South Indian; Transcription; Transcription factor; Variant alleles

Indexed keywords

CYCLOGUANIL; CYTOCHROME P450 2C19; LAVERAN; PROGUANIL; UNCLASSIFIED DRUG;

ADULT; ALLELE; AMINO ACID SEQUENCE; ARTICLE; BINDING SITE; COMPUTER MODEL; CONTROLLED STUDY; DNA BINDING; DNA FLANKING REGION; DRUG BLOOD LEVEL; DRUG OXIDATION; DRUG PROTEIN BINDING; EXON; FEMALE; GENE INTERACTION; GENE SEQUENCE; GENETIC POLYMORPHISM; GENETIC VARIABILITY; GENOTYPE; GENOTYPE PHENOTYPE CORRELATION; HUMAN; HUMAN EXPERIMENT; MALE; METABOLITE; MOLECULAR DOCKING; NORMAL HUMAN; NUCLEOTIDE SEQUENCE; PROMOTER REGION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SINGLE DRUG DOSE;

EID: 73349121669     PISSN: 13474367     EISSN: 18800920     Source Type: Journal    
DOI: 10.2133/dmpk.24.537     Document Type: Article

References (34)

1. Ingelman-Sundberg, Sim, S. C. Gomez, A. and Rodriguez, A. C.: Influence of cytochrome P450 polymorphisms on drug therapies: pharmacogenetic, pharmacoepigenetic and clinical aspects. Pharmacol. Ther., 116: 496-526 (2007).
2. Desta, Z., Zhao, X., Shin, J. G. and Flockart, D. A.: Clinical significance of the cytochrome P450 2C19 genetic polymorphism. Clin. Pharmacokinet., 41: 913-958 (2002).
3. Bolaji, O. O., Sadare, I. O., Babalola, C. P. and Ogunbona, F. A.: Polymorphic oxidative metabolism of proguanil in anigerian population. Eur. J. Clin. Pharmacol., 58: 543-545 (2002).
4. Ward, S. A., Helsby, N. A., Skielbo, E., Brosen, K., Gram, L. F. and Breckenridge, A. M.: The activation of the biguanide antimalarial proguanil co-segregates with the mephenytoin oxidation polymorphism-a panel study. Br. J. Clin. Pharmacol., 31: 689-692 (1991).
5. Goldstein, J. A., Ishizaki, T., Chiba, K., de Morais, S. M., Bell, D. Krahn, P. M. and Evans, D. A.: Frequencies of the defective CYP2C19 alleles responsible for the mephenytoin poor metabolizer phenotype in various Oriental, Caucasian, Saudi Arabian and American black populations. Pharmacogenetics, 7: 59-64 (1997).
6. Herrlin, K., Massele, A. Y., Jande, M., Alm, C., Tybring, G., Abdi, Y. A., Wennerholm, A., Johansson, I., Dahl, M. L., Bertilsson, L. and Gustafsson, L. L.: Bantu Tanzanians have a decreased capacity to metabolize omeprazole and mephenytoin in relation to their CYP2C19 genotype. Clin. Pharmacol. Ther., 64: 391-401 (1998).
7. Adithan, C., Gerard, N., Vasu, S., Balakrishnan, R., Shashindran, C. H. and Krishnamoorthy, R.: Allele and genotype frequency of CYP2C19 in a Tamilian population. Br. J. Clin. Pharmacol., 56: 331-333 (2003).
8. Tassaneeyakul, W., Mahatthanatrakul, W., Niwatananun, K., Na-Bangchang, K., Tawalee, A., Krikreangsak, N., Cykleng, U. and Tassaneeyakul, W.: CYP2C19 genetic polymorphism in Thai, Burmese and Karen populations. Drug. Metab. Pharmacokinet., 21: 286-290 (2006).
9. Partovian, C., Jaqcqz-Aigrain, E., Keundijian, A., Jaillon, P. and Funck-Brentano, C.: Comparison of chloroguanide and mephenytoin for the in-vivo assessment of genetically determined CYP2C19 activity in humans. Clin. Pharmacol. Ther., 58: 257-263 (1995).
10. Basci, N. E., Bozkurt, A., Kortunay, S., Isimer, A., Sayal, A. and Kayaalp, S. O.: Proguanil metabolism in relation to Smephenytoin oxidation in a Turkish population. Br. J. Clin. PharPharmacol., 42: 771-773 (1996).
11. Hoskins, J. M., Shenfield, G. M. and Gross, A. S.: Relationship between proguanil metabolic ratio and CYP2C19 genotype in a Caucasian population. Br. J. Clin. Pharmacol., 46: 499-504 (1998).
12. Hoskins, J. M., Shenfield, G. M. and Gross, A. S.: Concordance between proguanil phenotype and CYP2C19 genotype in Chinese. Eur. J. Clin. Pharmacol., 59: 611-614 (2003).
13. Rosemary, J., Adithan, C., Padmaja, N., Shashindran, C. H., Gerard, N. and Krishnamoorthy, R.: The effect of the CYP2C19 genotype on the hydroxylation index of omeprazole in South Indians. Eur. J. Clin. Pharmacol., 61: 19-23 (2005).
14. Coller, J. K., Somogyi, A. A. and Bochner, F.: Comparison of (S)- mephenytoin and proguanil oxidation in vitro: contribution of several CYP isoforms. Br. J. Clin. Pharmacol., 48: 158-167 (1999).
15. Setiabudy, R., Kusaka, M., Chiba, K., Darmansjah, I. and Ishizaki, T.: Metabolic disposition of proguanil in extensive and poor metabolisers of S-mephenytoin 4′-hydroxylation recruited from an Indonesian population. Br. J. Clin. Pharmacol., 39: 297-303 (1995).
16. Nowak, M. P., Sellers, E. M. and Tyndale, R. F.: Canadian Native Indians exhibit unique CYP2A6 and CYP2C19 mutant allele frequencies. Clin. Pharmacol. Ther., 64: 378-383 (1998).
17. Satyanarayana, C. R., Devendran, A., Sundaram, R., Gopal, S. D., Rajagopal, K. and Chandrasekaran, A.: Genetic variations and haplotypes of 5′ regulatory region of CYP2C19 in South Indian population. Drug. Metab. Pharmacokinet., 24: 185-193 (2009).
18. Arnott, S., Smith, P. J. C. and Chandrasekaran, R.: Atomic coordinates and molecular conformations for DNA-DNA., RNA- RNA and DNA-RNA helices. In Fasman, G. D. (ed.): Handbook of Biochemistry and Molecular Biology, Cleveland, CRC Press, 1975, pp. 411-422.
19. Kaplan, W. and Littlejohn, T. G.: Swiss-PDB Viewer (Deep View). Brief. Bioinform., 2: 195-197 (2001).
20. Lovell, S. C., Davis, I. W., Arendall, W. B., de Bakker, P. I., Word, J. M., Prisant, M. G., Richardson, J. S. and Richardson, D. C.: Structure validation by C alpha geometry: phi., psi and C beta deviation. Protein, 50: 437-450 (2003).
21. Duhovny, D., Nussinov, R. and Wolfson, H. J.: Efficient unbound docking of rigid molecules. In Guigo, R. and Gusfield, D. (eds.): Proceedings of the Fourth International Workshop on Algorithms in Bioinformatics, GmbH Rome, Italy, Springer-Verlag, 2002, pp. 185-200.
22. Luscombe, N. M., Laskowski, R. A. and Thornton, J. M.: NUC-PLOT: a program to generate schematic diagams of protein-DNA interactions. Nucleic. Acids. Res., 25: 4940-4945 (1997).
23. de Morais, S. M., Goldstein, J. A., Xie, H. G., Huang, S. L., Lu, Y. Q., Xia, H., Xiao, Z. S., Ile, N. and Zhou, H. H.: Genetic analysis of the S-mephenytoin polymorphism in Chinese population. Clin. Pharmacol. Ther., 58: 404-411 (1995).
24. Edeki, T. I., Goldstein, J. A., de Morais, S. M., Hajiloo, L., Butler, M., Chapdelaine, P. and Wilkinson, G. R.: Genetic polymorphism of S-mephenytoin 4′-hydroxylation in African-Americans. Pharmacogenetics, 6: 357-360 (1996).
25. Ieiri, I., Kubota, T., Urae A., Kimura, M., Wada, Y., Mamiya, K., Yoshioka, S., Irie, S., Amamoto, T., Nakamura, K., Nakano, S. and Higuchi, S.: Pharmacokinetics of omeprazole (a substrate of CYP2C19): and comparison with two mutant alleles, CYP2C19m1 in exon 5 and CYP2C19m2 in exon 4, in Japanese subjects. Clin. Pharmacol. Ther., 59: 647-653 (1996).
26. Wang, J. H., Li, P. Q., Fu, Q. Y., Li, Q. X. and Cai, W. W.: CYP2C19 genotype and omeprazole hydroxylation phenotype in Chinese Li population. Clin. Exp. Pharmacol. Physiol., 34: 421-424 (2007).
27. Funck-Brentano, C., Becquemont, L., Leneveu, A., Roux, A., Jaillon, P. and Beaune, P.: Inhibition by omeprazole of proguanil metabolism: Mechanism of the interaction in vitro and prediction of in vivo results from the in vitro experiments. J. Pharmacol. Exp. Ther., 280: 730-738 (1997).
28. Sim, S. C., Risinger, C., Dahl, M. L., Aklillu, E., Christensen, M., Bertilsson, L. and Ingelman-Sundberg, M. A.: Common novel CYP2C19 gene variant causes ultrarapid drug metabolism relevant for the drug response to proton pump inhibitors and antidepressants. Clin. Pharmacol. Ther., 79: 103-113 (2006).
29. Antes, T. J., Chen, J., Cooper, A. D. and Levy-Wilson, B.: The nuclear matrix protein CDP represses hepatic transcription of the human cholesterol-7alpha hydroxylase gene. J. Biol. Chem., 275: 26649-26660 (2000).
30. Shuman, J. D., Cheong, J. and Coligan, J. E.: ATF-2 and C/EBPalpha can form a heterodimeric DNA binding complex in vitro. Functional implications for transcriptional regulation. J. Biol. Chem., 272: 12793-800 (1997).
31. Jover, R., Bort, R., Gomez-Lechon, M. J. and Castel, J. V.: Re-expression of C/EBPa induces CYP2B6., CYP2C9., and CYP2D6 genes in HepG2 cells. FEBS Lett., 431: 227-230 (1998).
32. Chen, Y., Ferguson, S. S., Negishi, M. and Goldstein, J. A.: Identification of constitutive androstane receptor and glucocorticoid receptor binding sites in the CYP2C19 promoter. Mol. Pharmacol., 64: 316-324 (2003).
33. Yasui-Furukori, N., Takahata, T., Nakagami, T., Yoshiya, G., Inoue, Y., Kaneko, S. and Tateishi, T.: Different inhibitory effect of fluvoxamine on omeprazole metabolism between CYP2C19 genotypes. Br. J. Clin. Pharmacol., 57: 487-494 (2004).
34. Yin, O. Q., Tomlinson, B., Waye, M. M., Chow, A. H. and Chow, M. S.: Pharmacogenetics and herb-drug interactions: experience with Ginkgo biloba and omeprazole. Pharmacogenetics, 14: 841-850 (2004).