Enzyme kinetics for the formation of 3-hydroxyquinine and three new metabolites of quinine in vitro; 3-hydroxylation by CYP3A4 is indeed the major metabolic pathway

Drug Metabolism and Disposition

Volumn 30, Issue 12, 2002, Pages 1368-1371

  Mirghani, Rajaa A ^a,b,c   Yasar, Ümit ^a,b   Zheng, Tao ^a,b   Cook, James M ^a,b   Gustafsson, Lars L ^a,b   Tybring, Gunnel ^a,b   Ericsson, Örjan ^a,b  

^a KAROLINSKA INSTITUTE   (Sweden)

^b UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

^c KAROLINSKA UNIVERSITY HOSPITAL   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

10,11 DIHYDROXYDIHYDROQUININE; 2' QUININONE; 3 HYDROXYQUININE; CYTOCHROME P450 1A2; CYTOCHROME P450 2C19; CYTOCHROME P450 2C9; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; DRUG METABOLITE; FLUVOXAMINE; HYDROQUININE; KETOCONAZOLE; QUININE; RECOMBINANT ENZYME; TROLEANDOMYCIN; UNCLASSIFIED DRUG; 3 HYDROXYQUINIDINE; 3-HYDROXYQUINIDINE; CYP3A PROTEIN, HUMAN; CYP3A4 PROTEIN, HUMAN; CYTOCHROME P450; DRUG DERIVATIVE; QUINIDINE;

ARTICLE; DRUG HYDROXYLATION; DRUG METABOLISM; DRUG TRANSFORMATION; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME KINETICS; HUMAN; HUMAN TISSUE; LIVER MICROSOME; PRIORITY JOURNAL; ENZYMOLOGY; HYDROXYLATION; METABOLISM; PHARMACOKINETICS;

CINCHONA PUBESCENS;

CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; HYDROXYLATION; MICROSOMES, LIVER; PHARMACOKINETICS; QUINIDINE; QUININE;

EID: 0036892715     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.30.12.1368     Document Type: Article

References (18)

1. Bannon P, Yu P, Cook JM, Roy L, and Villeneuve JP (1998) Identification of quinine metabolites in urine after oral dosing in humans. J Chromatogr B Biomed Sci Appl 715:387-393.
2. Brosen K, Skjelbo E, Rasmussen BB, Poulsen HE, and Loft S (1993) Fluvoxamine is a potent inhibitor of cytochrome P4501A2. Biochem Pharmacol 45:1211-1214.
3. Chang TK, Gonzalez FJ, and Waxman DJ (1994) Evaluation of triacetyloleandomycin, alphanaphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Arch Biochem Biophys 311:437-442.
4. Diaz-Arauzo H, Cook JM, and Christie DJ (1990) Synthesis of 10,11-dihydroxydihydroquinidine N-oxide, a new metabolite of quinidine. Preparation and 1H-nmr spectroscopy of the metabolites of quinine and quinidine and conformational analysis via 2D COSY nmr spectroscopy. J Nat Prod 53:112-124.
5. Fleishaker JC and Hulst LK (1994) A pharmacokinetic and pharmacodynamic evaluation of the combined administration of alprazolam and fluvoxamine. Eur J Clin Pharmacol 46:35-39.
6. Gascon MP and Dayer P (1991) In vitro forecasting of drugs which may interfere with the biotransformation of midazolam. Eur J Clin Pharmacol 41:573-578.
7. Jeppesen U, Rasmussen BB, and Brosen K (1997) Fluvoxamine inhibits the CYP2C19-catalyzed bioactivation of chloroguanide. Clin Pharmacol Ther 62:279-286.
8. Krishna S and White NJ (1996) Pharmacokinetics of quinine, chloroquine and amodiaquine. Clinical implications. Clin Pharmacokinet 30:263-299.
9. Kuehl P, Zhang J, Lin Y, Lamba J, Assem M, Schuetz J, Watkins PB, Daly A, Wrighton SA, Hall SD, et al. (2001) Sequence diversity in CYP3A promoters and characterization of the genetic basis of polymorphic CYP3A5 expression. Nat Genet 27:383-391.
10. Lowry OH, Rosebrough NJ, Farr AI and Randall RJ (1951) Protein measurements with the folin phenol reagent. J Biol Chem 193:265-275.
11. Mirghani RA, Ericsson O, Cook J, Yu P, and Gustafsson LL (2001) Simultaneous determination of quinine and four metabolites in plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl 754:57-64.
12. Mirghani RA, Hellgren U, Westerberg PA, Ericsson O, Bertilsson L, and Gustafsson LL (1999) The roles of cytochrome P450 3A4 and 1A2 in the 3-hydroxylation of quinine in vivo. Clin Pharmacol Ther 66:454-460.
13. von Bahr C, Groth CG, Jansson H, Lundgren G, Lind M, and Glaumann H (1980) Drug metabolism in human liver in vitro: Establishment of a human liver bank. Clin Pharmacol Ther 27:711-725.
14. Wanwimolruk S, Wong SM, Zhang H, Coville PF, and Walker RJ (1995) Metabolism of quinine in man: Identification of a major metabolite and effects of smoking and rifampicin pretreatment. J Pharm Pharmacol 47:957-963.
15. White N (1992) Antimalarial pharmacokinelics and treatment regimens. Br J Clin Pharmacol 34:1-10.
16. Zhang H, Coville PF, Walker RJ, Miners JO, Birkett DJ, and Wanwimolruk S (1997) Evidence for involvement of human CYP3A in the 3-hydroxylalion of quinine. Br J Clin Pharmacol 43:245-252.
17. Zhao XJ and Ishizaki T (1997) Metabolic interactions of selected antimalarial and non-antimalarial drugs with the major pathway (3-hydroxylation) of quinine in human liver microsomes. Br J Clin Pharmacol 44:505-511.
18. Zheng T, Flippen-Anderson J, Yu P, Wang T, Mirghani R, and Cook JM (2001) Stereocontrolled conversion of quinine into 10(R), 11-dihydroxydihydroquinine via the sharpless osmylation process. J Org Chem 66:1509-1511.