메뉴 건너뛰기




Volumn 47, Issue 4, 1999, Pages 403-412

Methadone N-demethylation in human liver microsomes: Lack of stereoselectivity and involvement of CYP3A4

Author keywords

CYP3A4; EDDP formation; Human liver microsomes; Methadone N demethylation; Stereoselectivity

Indexed keywords

2 ETHYLIDENE 1,5 DIMETHYL 3,3 DIPHENYLPYRROLIDINE; COUMARIN; CYTOCHROME P450; CYTOCHROME P450 2C19; CYTOCHROME P450 3A4; DEBRISOQUINE 4 HYDROXYLASE; DIETHYLTHIOCARBAMATE; DIMETHYLNITROSAMINE DEMETHYLASE; ENZYME INHIBITOR; FURAFYLLINE; KETOCONAZOLE; MEPHENYTOIN; METHADONE; MONOCLONAL ANTIBODY; OPIATE AGONIST; PHENACETIN O DEETHYLASE; QUINIDINE; SULFAPHENAZOLE; TROLEANDOMYCIN; UNCLASSIFIED DRUG;

EID: 0032903876     PISSN: 03065251     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1365-2125.1999.00921.x     Document Type: Article
Times cited : (177)

References (44)
  • 1
    • 0028970418 scopus 로고
    • The mu1, mn2, delta, kappa opioid receptor binding profiles of methadone stereoisomers and morphine
    • 1 Kristensen K, Christensen CB, Christrup LL. The mu1, mn2, delta, kappa opioid receptor binding profiles of methadone stereoisomers and morphine. Life Sci 1995; 56: 45-50.
    • (1995) Life Sci , vol.56 , pp. 45-50
    • Kristensen, K.1    Christensen, C.B.2    Christrup, L.L.3
  • 2
    • 78651012481 scopus 로고
    • Pharmacologic comparison of the optical isomers of methadon
    • 2 Scott CC, Robbins EB, Chen KK. Pharmacologic comparison of the optical isomers of methadon. J Pharmacol Exp Ther 1948; 93: 282-286.
    • (1948) J Pharmacol Exp Ther , vol.93 , pp. 282-286
    • Scott, C.C.1    Robbins, E.B.2    Chen, K.K.3
  • 3
    • 84873758541 scopus 로고
    • The addiction liability of some of the drugs of the methadon series
    • 3 Isbell H, Eisenman AJ. The addiction liability of some of the drugs of the methadon series. Fed Proc 1948; 7: 162.
    • (1948) Fed Proc , vol.7 , pp. 162
    • Isbell, H.1    Eisenman, A.J.2
  • 4
    • 0029980977 scopus 로고    scopus 로고
    • Stereoselective pharmacokinetics of methadone in chronic pain patients
    • 4 Kristensen K, Blemmer T, Angelo HR, et al. Stereoselective pharmacokinetics of methadone in chronic pain patients. Ther Drug Monit 1996; 18: 221-227.
    • (1996) Ther Drug Monit , vol.18 , pp. 221-227
    • Kristensen, K.1    Blemmer, T.2    Angelo, H.R.3
  • 5
    • 0025246216 scopus 로고
    • Binding of d-methadone, l-methadone, and dl-methadone to proteins in plasma of healthy volunteers: Role of the variants of alpha 1-acid glycoprotein
    • 5 Eap CB, Cuendet C, Baumann P. Binding of d-methadone, l-methadone, and dl-methadone to proteins in plasma of healthy volunteers: role of the variants of alpha 1-acid glycoprotein. Clin Pharmacol Ther 1990; 47: 338-346.
    • (1990) Clin Pharmacol Ther , vol.47 , pp. 338-346
    • Eap, C.B.1    Cuendet, C.2    Baumann, P.3
  • 6
    • 0019515320 scopus 로고
    • Methadone binding to orosomucoid (alpha 1-acid glycoprotein): Determinant of free fraction in plasma
    • 6 Romach MK, Piafsky KM, Abel JG, Khouw V, Sellers EM. Methadone binding to orosomucoid (alpha 1-acid glycoprotein): determinant of free fraction in plasma. Clin Pharmacol Ther 1981; 29: 211-217.
    • (1981) Clin Pharmacol Ther , vol.29 , pp. 211-217
    • Romach, M.K.1    Piafsky, K.M.2    Abel, J.G.3    Khouw, V.4    Sellers, E.M.5
  • 7
    • 0000239305 scopus 로고
    • Metabolism of d-methadone: Isolation and identification of analgesically active metabolites
    • 7 Sullivan HR, Smits SE, Due SL, Booher RE, McMahon RE. Metabolism of d-methadone: Isolation and identification of analgesically active metabolites. Life Sci 1972; 11: 1093-1104.
    • (1972) Life Sci , vol.11 , pp. 1093-1104
    • Sullivan, H.R.1    Smits, S.E.2    Due, S.L.3    Booher, R.E.4    McMahon, R.E.5
  • 8
    • 0015873764 scopus 로고
    • Urinary metabolites of dl-methadone in maintenance subjects
    • 8 Sullivan HR, Duc SL. Urinary metabolites of dl-methadone in maintenance subjects. J Med Chem 1973; 16: 909-913.
    • (1973) J Med Chem , vol.16 , pp. 909-913
    • Sullivan, H.R.1    Duc, S.L.2
  • 11
    • 0029944684 scopus 로고    scopus 로고
    • Involvement of cytochrome P450 3A4 enzyme in the N-demethylation of methadone in human liver microsomes
    • 11 Iribarne C, Berthou F, Baird S, et al. Involvement of cytochrome P450 3A4 enzyme in the N-demethylation of methadone in human liver microsomes. Chem Res Toxicol 1996; 9: 365-373.
    • (1996) Chem Res Toxicol , vol.9 , pp. 365-373
    • Iribarne, C.1    Berthou, F.2    Baird, S.3
  • 12
    • 0031566987 scopus 로고    scopus 로고
    • Interaction of methadone with substrates of human hepatic cytochrome P450 3A4
    • 12 Iribarne C, Dreano Y, Bardou LG, Menez JF, Berthou F. Interaction of methadone with substrates of human hepatic cytochrome P450 3A4. Toxicol 1997; 117: 13-23.
    • (1997) Toxicol , vol.117 , pp. 13-23
    • Iribarne, C.1    Dreano, Y.2    Bardou, L.G.3    Menez, J.F.4    Berthou, F.5
  • 13
    • 0031942863 scopus 로고    scopus 로고
    • Inhibition of methadone and buprenorphine N-dealkylations by three HIV-1 protease inhibitors
    • 13 Iribarne C, Berthou F, Carlhant D, et al. Inhibition of methadone and buprenorphine N-dealkylations by three HIV-1 protease inhibitors. Drug Metab Dispos 1998; 26: 257-260.
    • (1998) Drug Metab Dispos , vol.26 , pp. 257-260
    • Iribarne, C.1    Berthou, F.2    Carlhant, D.3
  • 14
    • 0031448854 scopus 로고    scopus 로고
    • The involvement of cytochrome P450 3A4 in the N demethylation of 1-alpha acetylmethadol (laam), norlaam, and methadone
    • 14 Moody DE, Alburges ME, Parker RJ, Collins JM, Strong JM. The involvement of cytochrome P450 3A4 in the N demethylation of 1-alpha acetylmethadol (laam), norlaam, and methadone. Drug Metab Dispos 1997; 25: 1347-1353.
    • (1997) Drug Metab Dispos , vol.25 , pp. 1347-1353
    • Moody, D.E.1    Alburges, M.E.2    Parker, R.J.3    Collins, J.M.4    Strong, J.M.5
  • 15
    • 0023684586 scopus 로고
    • Absence of hepatic cytochrome P450bufl causes genetically deficient debrisoquine oxidation in man
    • 15 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.
    • (1988) Biochemistry , vol.27 , pp. 5447-5454
    • Zanger, U.M.1    Vilbois, F.2    Hardwick, J.P.3    Meyer, U.A.4
  • 17
    • 0000622703 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes, II solubilisation, purification and properties
    • 17 Omura T, Sato R. The carbon monoxide-binding pigment of liver microsomes, II Solubilisation, purification and properties. J Biol Chem 1964; 234: 2374-2385.
    • (1964) J Biol Chem , vol.234 , pp. 2374-2385
    • Omura, T.1    Sato, R.2
  • 18
    • 0029102348 scopus 로고
    • Detection of the poor metabolizer-associated CYP2D6 (D) gene deletion allele by long PCR technology
    • 18 Steen VM, Andreassen OA, Daly AK, et al. Detection of the poor metabolizer-associated CYP2D6 (D) gene deletion allele by long PCR technology. Pharmacogenetics 1995; 5: 215-223.
    • (1995) Pharmacogenetics , vol.5 , pp. 215-223
    • Steen, V.M.1    Andreassen, O.A.2    Daly, A.K.3
  • 19
    • 0025080352 scopus 로고
    • Genotyping of poor metabolisers of debrisoquine by allele-specific PCR amplification
    • 19 Heim M, Meyer UA. Genotyping of poor metabolisers of debrisoquine by allele-specific PCR amplification. Lancet 1990; 336: 529-532.
    • (1990) Lancet , vol.336 , pp. 529-532
    • Heim, M.1    Meyer, U.A.2
  • 20
    • 0030738072 scopus 로고    scopus 로고
    • Association between CYP2C19 genotype and proguanil oxidative polymorphism
    • 20 Coller JK, Somogyi AA, Bochner F. Association between CYP2C19 genotype and proguanil oxidative polymorphism. Br J Clin Pharmacol 1997; 43: 659-660.
    • (1997) Br J Clin Pharmacol , vol.43 , pp. 659-660
    • Coller, J.K.1    Somogyi, A.A.2    Bochner, F.3
  • 21
    • 0028858960 scopus 로고
    • Cytochrome P 450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes
    • 21 Newton DJ, Wang RW, Lu AY. Cytochrome P 450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metab Dispos 1995; 23: 154-158.
    • (1995) Drug Metab Dispos , vol.23 , pp. 154-158
    • Newton, D.J.1    Wang, R.W.2    Lu, A.Y.3
  • 22
    • 0027935778 scopus 로고
    • Diazepam metabolism by human liver microsomes is mediated by both S-mephenytoin hydroxylase and CYP3A isoforms
    • 22 Andersson T, Miners JO, Veronese ME, Birkett DJ. Diazepam metabolism by human liver microsomes is mediated by both S-mephenytoin hydroxylase and CYP3A isoforms. Br J Clin Pharmacol 1994; 38: 131-137.
    • (1994) Br J Clin Pharmacol , vol.38 , pp. 131-137
    • Andersson, T.1    Miners, J.O.2    Veronese, M.E.3    Birkett, D.J.4
  • 23
    • 0028898816 scopus 로고
    • Inhibition of alprazolam and desipramme hydroxylation in vitro by paroxetine and fluvoxamine: Comparison with other selective serotonin reuptake inhibitor antidepressants
    • 23 von Moltke LL, Greenblatt DJ, Court MH, Duan SX, Harmatz JS, Shader RI. Inhibition of alprazolam and desipramme hydroxylation in vitro by paroxetine and fluvoxamine: comparison with other selective serotonin reuptake inhibitor antidepressants. J Clin Psychopharmacol 1995; 15: 125-131.
    • (1995) J Clin Psychopharmacol , vol.15 , pp. 125-131
    • Von Moltke, L.L.1    Greenblatt, D.J.2    Court, M.H.3    Duan, S.X.4    Harmatz, J.S.5    Shader, R.I.6
  • 24
    • 0030928512 scopus 로고    scopus 로고
    • An update on the clinical use of methadone for cancer pain
    • 24 Ripamonti C, Zecca E, Bruera E. An update on the clinical use of methadone for cancer pain. Pain 1997; 70: 109-115.
    • (1997) Pain , vol.70 , pp. 109-115
    • Ripamonti, C.1    Zecca, E.2    Bruera, E.3
  • 25
    • 0028237729 scopus 로고
    • Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians
    • 25 Shimada T, Yamazaki H, Mimura M, Inui Y, Guengerich FP. Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther 1994; 270: 414-123.
    • (1994) J Pharmacol Exp Ther , vol.270 , pp. 414-1123
    • Shimada, T.1    Yamazaki, H.2    Mimura, M.3    Inui, Y.4    Guengerich, F.P.5
  • 26
    • 0030006119 scopus 로고    scopus 로고
    • Characterization of microsomal cytochrome P450 enzymes involved in the oxidation of xenobiotic chemicals in human fetal liver and adult lungs
    • 26 Shimada T, Yamazaki H, Mimura M, et al. Characterization of microsomal cytochrome P450 enzymes involved in the oxidation of xenobiotic chemicals in human fetal liver and adult lungs. Drug Metab Dispos 1996; 24: 515-522.
    • (1996) Drug Metab Dispos , vol.24 , pp. 515-522
    • Shimada, T.1    Yamazaki, H.2    Mimura, M.3
  • 27
    • 0024855057 scopus 로고
    • Carbamazepine treatment of cocaine dependence in methadone maintenance patients with dual opiate-cocaine addiction
    • 27 Kuhn KL, Halikas JA, Kemp KD. Carbamazepine treatment of cocaine dependence in methadone maintenance patients with dual opiate-cocaine addiction. NIDA Res Monogr 1989; 95: 316-317.
    • (1989) NIDA Res Monogr , vol.95 , pp. 316-317
    • Kuhn, K.L.1    Halikas, J.A.2    Kemp, K.D.3
  • 28
    • 0024337518 scopus 로고
    • Valproic acid, unlike other anticonvulsants, has no effect on methadone metabolisin: Two cases
    • 28 Saxon AJ, Whittaker S, Hawker CS. Valproic acid, unlike other anticonvulsants, has no effect on methadone metabolisin: two cases. J Clin Psychiatry 1989; 50: 228-229.
    • (1989) J Clin Psychiatry , vol.50 , pp. 228-229
    • Saxon, A.J.1    Whittaker, S.2    Hawker, C.S.3
  • 30
    • 0021126970 scopus 로고
    • Case report of barbiturate induced enhancement of methadone metabolism and withdrawal syndrome
    • 30 Liu SJ, Wang RI. Case report of barbiturate induced enhancement of methadone metabolism and withdrawal syndrome. Am J Psychiatry 1984; 141: 1287-1288.
    • (1984) Am J Psychiatry , vol.141 , pp. 1287-1288
    • Liu, S.J.1    Wang, R.I.2
  • 32
    • 0025689294 scopus 로고
    • Evidence for altered desipramine disposition in methadone-maintained patients treated for cocaine abuse
    • 32 Kosten TR, Gawin FH, Morgan C, Nelson JC, Jatlow P. Evidence for altered desipramine disposition in methadone-maintained patients treated for cocaine abuse. Am J Drug Alcohol Abuse 1990; 16: 329-336.
    • (1990) Am J Drug Alcohol Abuse , vol.16 , pp. 329-336
    • Kosten, T.R.1    Gawin, F.H.2    Morgan, C.3    Nelson, J.C.4    Jatlow, P.5
  • 34
    • 0028038065 scopus 로고
    • The role of CYP2D6 in primary and secondary oxidative metabolism of dextromethorphan: In vitro studies using human liver microsomes
    • 34 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: 243-248.
    • (1994) Br J Clin Pharmacol , vol.38 , pp. 243-248
    • Kerry, N.L.1    Somogyi, A.A.2    Bochner, F.3    Mikus, G.4
  • 35
    • 0027454958 scopus 로고
    • Inhibition of human cytochrome P450 2D6 (CYP2D6) by methadone
    • 35 Wu D, Otton SV, Sproule BA, et al. Inhibition of human cytochrome P450 2D6 (CYP2D6) by methadone. Br J Clin Phamacol 1993; 35: 30-34.
    • (1993) Br J Clin Phamacol , vol.35 , pp. 30-34
    • Wu, D.1    Otton, S.V.2    Sproule, B.A.3
  • 36
    • 0023873009 scopus 로고
    • In vitro evidence against the oxidation of quinidine by the sparteine/debrisoquine monooxygenase of human liver
    • 36 Otton SV, Brinn RU, Gram LF. In vitro evidence against the oxidation of quinidine by the sparteine/debrisoquine monooxygenase of human liver. Drug Metab Dispos 1988; 16: 15-17.
    • (1988) Drug Metab Dispos , vol.16 , pp. 15-17
    • Otton, S.V.1    Brinn, R.U.2    Gram, L.F.3
  • 37
    • 0028174881 scopus 로고
    • Evaluation of triacetyloleandomycin, alpha-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450
    • 37 Chang TK, Gonzalez FJ, Waxman DJ. Evaluation of triacetyloleandomycin, alpha-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Arch Biochem Biophys 1994; 311: 437-442.
    • (1994) Arch Biochem Biophys , vol.311 , pp. 437-442
    • Chang, T.K.1    Gonzalez, F.J.2    Waxman, D.J.3
  • 38
    • 0020064901 scopus 로고
    • Lack of effect of diazepam on methadone metabolism in methadone-maintained addicts
    • 38 Pond SM, Tong TG, Benowitz NL, Jacob PD, Rigod J. Lack of effect of diazepam on methadone metabolism in methadone-maintained addicts. Clin Pharmacol Ther 1982; 31: 139-143.
    • (1982) Clin Pharmacol Ther , vol.31 , pp. 139-143
    • Pond, S.M.1    Tong, T.G.2    Benowitz, N.L.3    Jacob, P.D.4    Rigod, J.5
  • 39
    • 0022452970 scopus 로고
    • Diazepam and methadone blood levels following concurrent administration of diazepam and methadone
    • 39 Preston KL, Griffiths RR, Cone EJ, Darwin WD, Gorodetzky CW. Diazepam and methadone blood levels following concurrent administration of diazepam and methadone. Drug Alcohol Depend 1986; 18: 195-202.
    • (1986) Drug Alcohol Depend , vol.18 , pp. 195-202
    • Preston, K.L.1    Griffiths, R.R.2    Cone, E.J.3    Darwin, W.D.4    Gorodetzky, C.W.5
  • 40
    • 0028279667 scopus 로고
    • Inhibitors of alprazolam metabolism in vitro: Effect of serotonin-reuptake inhibitor antidepressants, ketoconazole and quinidine
    • 40 von Moltke LL, Greenblatt DJ, Cotreau Bibbo MM, Harmatz JS, Shader RI. Inhibitors of alprazolam metabolism in vitro: effect of serotonin-reuptake inhibitor antidepressants, ketoconazole and quinidine. Br J Clin Pharmacol 1994; 38: 23-31.
    • (1994) Br J Clin Pharmacol , vol.38 , pp. 23-31
    • Von Moltke, L.L.1    Greenblatt, D.J.2    Cotreau Bibbo, M.M.3    Harmatz, J.S.4    Shader, R.I.5
  • 41
    • 0029976064 scopus 로고    scopus 로고
    • Newer antidepressants and the cytochrome P450 system
    • 41 Nemeroff CB, DeVane CL, Pollock BG. Newer antidepressants and the cytochrome P450 system. Am J Psychiatry 1996; 153: 311-320.
    • (1996) Am J Psychiatry , vol.153 , pp. 311-320
    • Nemeroff, C.B.1    Devane, C.L.2    Pollock, B.G.3
  • 42
    • 0028276695 scopus 로고
    • Identification of human liver cytochrome P450 isoforms mediating secondary omeprazole metabolism
    • 42 Andersson T, Miners JO, Veronese ME, Birkett DJ. Identification of human liver cytochrome P450 isoforms mediating secondary omeprazole metabolism. Br J Clin Pharmacol 1994; 37: 597-604.
    • (1994) Br J Clin Pharmacol , vol.37 , pp. 597-604
    • Andersson, T.1    Miners, J.O.2    Veronese, M.E.3    Birkett, D.J.4
  • 43
    • 0027145018 scopus 로고
    • Identification of human liver cytochrome P450 isoforms mediating omeprazole metabolism
    • 43 Andersson T, Miners JO, Veronese ME, et al. Identification of human liver cytochrome P450 isoforms mediating omeprazole metabolism. Br J Clin Pharmacol 1993; 36: 521-530.
    • (1993) Br J Clin Pharmacol , vol.36 , pp. 521-530
    • Andersson, T.1    Miners, J.O.2    Veronese, M.E.3
  • 44
    • 0030811096 scopus 로고    scopus 로고
    • Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms
    • 44 Ko J-W, Sukhova N, Thacker D, Chen P, Flockhart DA. Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms. Drug Metab Dispos 1997; 25: 853-862.
    • (1997) Drug Metab Dispos , vol.25 , pp. 853-862
    • Ko, J.-W.1    Sukhova, N.2    Thacker, D.3    Chen, P.4    Flockhart, D.A.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.