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Volumn 84, Issue 2, 1997, Pages 125-133

Biotransformation of taxoids by human cytochromes P450: Structure-activity relationship

Author keywords

CYP2C8; CYP3A4; docetaxel; human liver microsomes; induction; inhibition; interactions; metabolism; paclitaxel

Indexed keywords

BARBITURIC ACID DERIVATIVE; CIMETIDINE; CISPLATIN; CYTOCHROME P450; DIPHENHYDRAMINE; DOCETAXEL; DOXORUBICIN; DRUG METABOLITE; KETOCONAZOLE; PACLITAXEL; PACLITAXEL DERIVATIVE; RANITIDINE; VERAPAMIL; VINBLASTINE; VINCRISTINE;

EID: 0030957370     PISSN: 00074551     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (48)

References (59)
  • 3
    • 0028929475 scopus 로고
    • Synthesis and biological activity of para-substituted 3′-phenyl docetaxel analogs
    • Bourzat JM, Lavelle F, Commercon A. Synthesis and biological activity of para-substituted 3′-phenyl docetaxel analogs. Bioorg Med Chem Lett 1995; 5: 809-14.
    • (1995) Bioorg Med Chem Lett , vol.5 , pp. 809-814
    • Bourzat, J.M.1    Lavelle, F.2    Commercon, A.3
  • 5
    • 0022357068 scopus 로고
    • Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: A series of substrates to distinguish between different induced cytochromes P450
    • Burke MD, Thompson S, Elcombe CR, Halpert J, Haaparanta T, Mayer RT. Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochromes P450. Biochem Pharmacol 1985; 34: 3337-45.
    • (1985) Biochem Pharmacol , vol.34 , pp. 3337-3345
    • Burke, M.D.1    Thompson, S.2    Elcombe, C.R.3    Halpert, J.4    Haaparanta, T.5    Mayer, R.T.6
  • 7
    • 0019137067 scopus 로고
    • Neonatal imprinting and hepatic cytochrome P450. Comparison of testosterone hydroxylation in a reconstituted system between neonatally imprinted and nonimprinted rats
    • Chung LWK, Chao H. Neonatal imprinting and hepatic cytochrome P450. Comparison of testosterone hydroxylation in a reconstituted system between neonatally imprinted and nonimprinted rats. Mol Pharmacol 1980; 18: 543-9.
    • (1980) Mol Pharmacol , vol.18 , pp. 543-549
    • Chung, L.W.K.1    Chao, H.2
  • 8
    • 0018765003 scopus 로고
    • Effect of microsomal preparations and induction on cytochrome P450-dependent monooxygenases in fetal and neonatal rat liver
    • Cresteil T, Flinois JP, Pfister A, Leroux JP. Effect of microsomal preparations and induction on cytochrome P450-dependent monooxygenases in fetal and neonatal rat liver. Biochem Pharmacol 1979; 28: 2057-63.
    • (1979) Biochem Pharmacol , vol.28 , pp. 2057-2063
    • Cresteil, T.1    Flinois, J.P.2    Pfister, A.3    Leroux, J.P.4
  • 9
    • 0022356229 scopus 로고
    • Immunoquantification of epoxide hydrolase and cytochrome P-450 isoenzymes in fetal and adult human liver microsomes
    • Cresteil T, Beaune P, Kremers P, Celier C, Guengerich FP, Leroux JP. Immunoquantification of epoxide hydrolase and cytochrome P-450 isoenzymes in fetal and adult human liver microsomes. Eur J Biochem 1985; 151: 345-50.
    • (1985) Eur J Biochem , vol.151 , pp. 345-350
    • Cresteil, T.1    Beaune, P.2    Kremers, P.3    Celier, C.4    Guengerich, F.P.5    Leroux, J.P.6
  • 10
    • 0027954464 scopus 로고
    • Taxol metabolism by human liver microsomes: Identification of cytochrome P450 isozymes involved in its biotransformation
    • Cresteil T, Monsarrat B, Alvinerie P, Treluyer JM, Vieira I, Wright M. Taxol metabolism by human liver microsomes: identification of cytochrome P450 isozymes involved in its biotransformation. Cancer Res 1994; 54: 386-92.
    • (1994) Cancer Res , vol.54 , pp. 386-392
    • Cresteil, T.1    Monsarrat, B.2    Alvinerie, P.3    Treluyer, J.M.4    Vieira, I.5    Wright, M.6
  • 11
    • 0025344378 scopus 로고
    • Cytochrome P450 isoenzymes epoxide hydrolase and glutathione transferases in rat and human hepatic and extrahepatic tissues
    • De Waziers I, Cugnenc PH, Yang CS, Leroux JP, Beaune P. Cytochrome P450 isoenzymes epoxide hydrolase and glutathione transferases in rat and human hepatic and extrahepatic tissues. J Pharmacol Exp Ther 1990; 253: 387-94.
    • (1990) J Pharmacol Exp Ther , vol.253 , pp. 387-394
    • De Waziers, I.1    Cugnenc, P.H.2    Yang, C.S.3    Leroux, J.P.4    Beaune, P.5
  • 12
    • 0028894301 scopus 로고
    • Non linear pharmacokinetics and metabolism of paclitaxel and its pharmacokinetic/pharmacodynamic relationships in humans
    • Gianni L, Kearns CM, Giani A, Capri G, Vigano L, Locatelli A, Bonadonna G, Egorin MJ. Non linear pharmacokinetics and metabolism of paclitaxel and its pharmacokinetic/pharmacodynamic relationships in humans. J Clin Oncol 1995; 13: 180-90.
    • (1995) J Clin Oncol , vol.13 , pp. 180-190
    • Gianni, L.1    Kearns, C.M.2    Giani, A.3    Capri, G.4    Vigano, L.5    Locatelli, A.6    Bonadonna, G.7    Egorin, M.J.8
  • 13
    • 0024236331 scopus 로고
    • The molecular biology of cytochrome P450s
    • Gonzalez FJ. The molecular biology of cytochrome P450s. Pharmacol Rev 1989; 40: 243-88.
    • (1989) Pharmacol Rev , vol.40 , pp. 243-288
    • Gonzalez, F.J.1
  • 14
    • 0014721047 scopus 로고
    • Synthesesteigerung und abbauhemmung bei der vermchrung der mikrosomalen cytochrome P450 und b5 durch phenobarbital
    • Greim H. Synthesesteigerung und abbauhemmung bei der vermchrung der mikrosomalen cytochrome P450 und b5 durch phenobarbital. Arch Pharmacol 1970; 266: 261-75.
    • (1970) Arch Pharmacol , vol.266 , pp. 261-275
    • Greim, H.1
  • 16
    • 0023031049 scopus 로고
    • Chemical studies of 10-deacetylbaccatin III. Hemisynthesis of taxol derivatives
    • Gueritte-Voegelein F, Senilh V, David B, Guenard D, Potier P. Chemical studies of 10-deacetylbaccatin III. Hemisynthesis of taxol derivatives. Tetrahedron 1986; 42: 4451-60.
    • (1986) Tetrahedron , vol.42 , pp. 4451-4460
    • Gueritte-Voegelein, F.1    Senilh, V.2    David, B.3    Guenard, D.4    Potier, P.5
  • 18
    • 0028345782 scopus 로고
    • Isolation structural determination and biological activity of 6α-hydroxytaxol the principal human metabolite of taxol
    • Harris JW, Katki A, Anderson LW, Chmurny GN, Paukstelis JV, Collins JM. Isolation structural determination and biological activity of 6α-hydroxytaxol the principal human metabolite of taxol. J Med Chem 1994a; 37: 706-9.
    • (1994) J Med Chem , vol.37 , pp. 706-709
    • Harris, J.W.1    Katki, A.2    Anderson, L.W.3    Chmurny, G.N.4    Paukstelis, J.V.5    Collins, J.M.6
  • 19
    • 0027957132 scopus 로고
    • Metabolism of taxol by human hepatic microsomes and liver slices: Participotion of cytochrome P450 3A4 and an unknown P450 enzyme
    • Harris JW, Rahman A, Kim BR, Guengerich FP, Collins JM. Metabolism of taxol by human hepatic microsomes and liver slices: participotion of cytochrome P450 3A4 and an unknown P450 enzyme. Cancer Res 1994b; 54: 4026-35.
    • (1994) Cancer Res , vol.54 , pp. 4026-4035
    • Harris, J.W.1    Rahman, A.2    Kim, B.R.3    Guengerich, F.P.4    Collins, J.M.5
  • 21
    • 0029033491 scopus 로고
    • Tubulin alterations in taxol-induced apoptosis parallel those observed with other drugs
    • Ireland CM, Strickland D, Pittman SM. Tubulin alterations in taxol-induced apoptosis parallel those observed with other drugs. Biochem Pharmacol 1995; 49: 1491-9.
    • (1995) Biochem Pharmacol , vol.49 , pp. 1491-1499
    • Ireland, C.M.1    Strickland, D.2    Pittman, S.M.3
  • 22
    • 0023774226 scopus 로고
    • Purification and characterization of P450 isozyme isolated from liver of rats pretreated with clofibrate
    • Kiffel L, Celier C, Leroux JP. Purification and characterization of P450 isozyme isolated from liver of rats pretreated with clofibrate. Biochem Biophys Res Commun 1988; 156: 282-9.
    • (1988) Biochem Biophys Res Commun , vol.156 , pp. 282-289
    • Kiffel, L.1    Celier, C.2    Leroux, J.P.3
  • 24
    • 0023161810 scopus 로고
    • Comparative effects of H2-receptor antagonists on drug metabolism in vitro and in vivo
    • Klotz U, Arvela P, Pasanen M, Kroemer H, Pelkonen O. Comparative effects of H2-receptor antagonists on drug metabolism in vitro and in vivo. Pharmac Ther 1987; 3: 157-61.
    • (1987) Pharmac Ther , vol.3 , pp. 157-161
    • Klotz, U.1    Arvela, P.2    Pasanen, M.3    Kroemer, H.4    Pelkonen, O.5
  • 25
    • 0023355128 scopus 로고
    • Hepatic metabolism of tolbutamide: Characterization of the form of cytochrome P-450 involved in methyl hydroxylation and relationship to in vivo disposition
    • Knodell RG, Hall SD, Wilkinson GR and Guengerich FP. Hepatic metabolism of tolbutamide: characterization of the form of cytochrome P-450 involved in methyl hydroxylation and relationship to in vivo disposition. J Pharmacol Exp Ther 1987; 241: 1112-9.
    • (1987) J Pharmacol Exp Ther , vol.241 , pp. 1112-1119
    • Knodell, R.G.1    Hall, S.D.2    Wilkinson, G.R.3    Guengerich, F.P.4
  • 28
    • 0026778218 scopus 로고
    • Predictability of the in vivo metabolism of verapamil from in vitro data: Contribution of individual metabolic pathways and stereoselective aspects
    • Kroemer HK, Echizen H, Heidemann H, Eichelbaum M. Predictability of the in vivo metabolism of verapamil from in vitro data: contribution of individual metabolic pathways and stereoselective aspects. J Pharmacol Exp Ther 1992; 260: 1052-7.
    • (1992) J Pharmacol Exp Ther , vol.260 , pp. 1052-1057
    • Kroemer, H.K.1    Echizen, H.2    Heidemann, H.3    Eichelbaum, M.4
  • 29
    • 0028154073 scopus 로고
    • 6α-hydroxytaxol: Isolation and identification of the major metabolite of taxol in human liver microsomes
    • Kumar GN, Oatis JE, Thornburg KR, Heldrich FJ, Hazard ES, Walle T. 6α-hydroxytaxol: isolation and identification of the major metabolite of taxol in human liver microsomes. Drug Metab Dispos 1994a; 22: 177-9.
    • (1994) Drug Metab Dispos , vol.22 , pp. 177-179
    • Kumar, G.N.1    Oatis, J.E.2    Thornburg, K.R.3    Heldrich, F.J.4    Hazard, E.S.5    Walle, T.6
  • 30
    • 0028201724 scopus 로고
    • Cytochrome P450 3A-mediated human liver microsomal taxol 6α-hydroxylation
    • Kumar GN, Walle UK, Walle T. Cytochrome P450 3A-mediated human liver microsomal taxol 6α-hydroxylation. J Pharmacol Exp Ther 1994b; 268: 1160-5.
    • (1994) J Pharmacol Exp Ther , vol.268 , pp. 1160-1165
    • Kumar, G.N.1    Walle, U.K.2    Walle, T.3
  • 31
    • 0014949207 scopus 로고
    • Cleavage of structural proteins during the assembly of the head of bacteriophage T4
    • Laemmli UK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature (London) 1970; 227: 680-5.
    • (1970) Nature (London) , vol.227 , pp. 680-685
    • Laemmli, U.K.1
  • 32
    • 0001318007 scopus 로고
    • Relationship between the structures of taxol and baccatine III and their in vitro action on the disassembly of mammalian brain and Physarum amoebal microtubules
    • Lataste H, Senilh V, Wright M, Guenard D, Potier P. Relationship between the structures of taxol and baccatine III and their in vitro action on the disassembly of mammalian brain and Physarum amoebal microtubules. Proc Natl Acad Sci USA 1984; 81: 4090-4.
    • (1984) Proc Natl Acad Sci USA , vol.81 , pp. 4090-4094
    • Lataste, H.1    Senilh, V.2    Wright, M.3    Guenard, D.4    Potier, P.5
  • 33
    • 0020579608 scopus 로고
    • Immunological and enzymatic comparison of hepatic cytochrome P450 fractions from phenobarbital-, 3-methylcholanthrene-, β-naphthoflavone- and 2,3,7,8-tetrachlorodibenzo-p-dioxin-treated rots
    • LeProvost E, Cresteil T, Columelli S, Leroux JP. Immunological and enzymatic comparison of hepatic cytochrome P450 fractions from phenobarbital-, 3-methylcholanthrene-, β-naphthoflavone- and 2,3,7,8-tetrachlorodibenzo-p-dioxin-treated rots. Biochem Pharmacol 1983; 32: 1673-82.
    • (1983) Biochem Pharmacol , vol.32 , pp. 1673-1682
    • LeProvost, E.1    Cresteil, T.2    Columelli, S.3    Leroux, J.P.4
  • 41
    • 0028036727 scopus 로고
    • Selective biotransformation of laxol to 6α-hydroxylaxol by human cytochrome P450 2C8
    • Rahman A, Korzekwa KR, Grogan J, Gonzalez FJ, Harris JW. Selective biotransformation of laxol to 6α-hydroxylaxol by human cytochrome P450 2C8. Cancer Res 1994; 54: 5543-6.
    • (1994) Cancer Res , vol.54 , pp. 5543-5546
    • Rahman, A.1    Korzekwa, K.R.2    Grogan, J.3    Gonzalez, F.J.4    Harris, J.W.5
  • 42
    • 0025296575 scopus 로고
    • Cytochrome P450IIIA enzymes in rat liver microsomes. Involvement in C3-hydroxylation of diazepam and nordazepam but not N-dealkylation of diazepam and temazepam
    • Reilly PEB, Thompson DA, Mason SR, Hooper WD. Cytochrome P450IIIA enzymes in rat liver microsomes. Involvement in C3-hydroxylation of diazepam and nordazepam but not N-dealkylation of diazepam and temazepam. Mol Pharmacol 1990; 37: 767-74.
    • (1990) Mol Pharmacol , vol.37 , pp. 767-774
    • Reilly, P.E.B.1    Thompson, D.A.2    Mason, S.R.3    Hooper, W.D.4
  • 43
    • 0026428123 scopus 로고
    • Studies with RP 56976 (Taxotere): A semi-synthetic analog of taxol
    • Ringel I, Horwitz SB. Studies with RP 56976 (Taxotere): a semi-synthetic analog of taxol. J Natl Cancer Inst 1991; 83: 288-91.
    • (1991) J Natl Cancer Inst , vol.83 , pp. 288-291
    • Ringel, I.1    Horwitz, S.B.2
  • 44
    • 0026345003 scopus 로고
    • The clinical pharmacology and use of antimicrotubule agents in cancer chemotherapeutics
    • Rowinsky EK, Donehower RC. The clinical pharmacology and use of antimicrotubule agents in cancer chemotherapeutics. Pharmacol Ther 1991; 52: 35-84.
    • (1991) Pharmacol Ther , vol.52 , pp. 35-84
    • Rowinsky, E.K.1    Donehower, R.C.2
  • 46
    • 0029173748 scopus 로고
    • Paclitaxel metabolites in human plasma and urine: Identification of 6α-hydroxytaxol, 7-epitaxol and taxol hydrolysis products using liquid chromatography/atmospheric-pressure chemical ionization mass spectrometry
    • Royer I, Alvinerie P, Armand JP, Ho LK, Wright M, Monsarrat B. Paclitaxel metabolites in human plasma and urine: identification of 6α-hydroxytaxol, 7-epitaxol and taxol hydrolysis products using liquid chromatography/atmospheric-pressure chemical ionization mass spectrometry. Rapid Commun Mass Spectrom 1995; 9: 495-502.
    • (1995) Rapid Commun Mass Spectrom , vol.9 , pp. 495-502
    • Royer, I.1    Alvinerie, P.2    Armand, J.P.3    Ho, L.K.4    Wright, M.5    Monsarrat, B.6
  • 47
    • 0030051928 scopus 로고    scopus 로고
    • Metabolism of docetaxel by human cytochromes P450: Interactions with paclitaxel and other antineoplastic drugs
    • Royer I, Monsarrat B, Sonnier M, Wright M, Cresteil T. Metabolism of docetaxel by human cytochromes P450: interactions with paclitaxel and other antineoplastic drugs. Cancer Res 1996; 56: 58-65.
    • (1996) Cancer Res , vol.56 , pp. 58-65
    • Royer, I.1    Monsarrat, B.2    Sonnier, M.3    Wright, M.4    Cresteil, T.5
  • 48
    • 0018387446 scopus 로고
    • Promotion of microtubule assembly in vitro by taxol
    • Schiff PB, Fant J, Horwitz SB. Promotion of microtubule assembly in vitro by taxol. Nature 1979; 22: 665-7.
    • (1979) Nature , vol.22 , pp. 665-667
    • Schiff, P.B.1    Fant, J.2    Horwitz, S.B.3
  • 49
    • 0000297058 scopus 로고
    • Taxol stabilizes microtubules in mouse fibroblast cells
    • Schiff PB, Horwitz SB. Taxol stabilizes microtubules in mouse fibroblast cells. Proc Natl Acad Sci (USA) 1980; 77: 1561-5.
    • (1980) Proc Natl Acad Sci (USA) , vol.77 , pp. 1561-1565
    • Schiff, P.B.1    Horwitz, S.B.2
  • 52
    • 0028283518 scopus 로고
    • Characterization of the taxol structure-activity profile for the locus at the A-ring side chain
    • Swindell CS, Heerding JM, Krauss NE. Characterization of the taxol structure-activity profile for the locus at the A-ring side chain. Bioorg Med Chem Lett 1994; 4: 1531-6.
    • (1994) Bioorg Med Chem Lett , vol.4 , pp. 1531-1536
    • Swindell, C.S.1    Heerding, J.M.2    Krauss, N.E.3
  • 57
    • 0015211527 scopus 로고
    • Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia
    • Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 1971; 93: 2325-7.
    • (1971) J Am Chem Soc , vol.93 , pp. 2325-2327
    • Wani, M.C.1    Taylor, H.L.2    Wall, M.E.3    Coggon, P.4    McPhail, A.T.5


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