메뉴 건너뛰기




Volumn 308, Issue 2, 2004, Pages 547-554

Activation of G-Proteins by Morphine and Codeine Congeners: Insights to the Relevance of O- and N-Demethylated Metabolites at μ- and δ-Opioid Receptors

Author keywords

[No Author keywords available]

Indexed keywords

CODEINE; CYTOCHROME P450; DELTA OPIATE RECEPTOR; DIHYDROCODEINE; DIHYDROMORPHINE; DRUG DERIVATIVE; GUANINE NUCLEOTIDE BINDING PROTEIN; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); HYDROCODONE; HYDROMORPHONE; MORPHINE; MORPHINE DERIVATIVE; MU OPIATE RECEPTOR; NALOXONE; NARCOTIC AGENT; NORDIHYDROCODEINE; NORHYDROCODONE; NORHYDROMORPHINE; NORMORPHINE; NOROXYCODONE; NOROXYMORPHONE; OXYCODONE; OXYMORPHONE; UNCLASSIFIED DRUG;

EID: 1642457241     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.103.058602     Document Type: Article
Times cited : (80)

References (41)
  • 1
    • 0025827095 scopus 로고
    • Selective blockage of delta opioid receptors prevents the development of morphine tolerance and dependence in mice
    • Abdelhamid EE, Sultana M, Portoghese PS, and Takemori AE (1991) Selective blockage of delta opioid receptors prevents the development of morphine tolerance and dependence in mice. J Pharmacol Exp Ther 258:299-303.
    • (1991) J Pharmacol Exp Ther , vol.258 , pp. 299-303
    • Abdelhamid, E.E.1    Sultana, M.2    Portoghese, P.S.3    Takemori, A.E.4
  • 2
    • 0021712818 scopus 로고
    • Catecholamine-stimulated guanosine 5′-O-(3-thiotriphosphate) binding to the stimulatory GTP-binding protein of adenylyl cyclase: Kinetic analysis in reconstituted phospholipid vesicles
    • Asano T and Ross EM (1984) Catecholamine-stimulated guanosine 5′-O-(3-thiotriphosphate) binding to the stimulatory GTP-binding protein of adenylyl cyclase: kinetic analysis in reconstituted phospholipid vesicles. Biochemistry 23:5467-5471.
    • (1984) Biochemistry , vol.23 , pp. 5467-5471
    • Asano, T.1    Ross, E.M.2
  • 3
    • 0029680208 scopus 로고    scopus 로고
    • Microsomal codeine N-demethylation: Cosegregation with cytochrome P4503A4 activity
    • Caraco Y, Tateishi T, Guengerich FP, and Wood AJ (1996) Microsomal codeine N-demethylation: cosegregation with cytochrome P4503A4 activity. Drug Metab Dispos 24:761-764.
    • (1996) Drug Metab Dispos , vol.24 , pp. 761-764
    • Caraco, Y.1    Tateishi, T.2    Guengerich, F.P.3    Wood, A.J.4
  • 4
    • 0025830147 scopus 로고
    • Mu receptor binding of some commonly used opioids and their metabolites
    • Chen ZR, Irvine RJ, Somogyi AA, and Bochner F (1991) Mu receptor binding of some commonly used opioids and their metabolites. Life Sci 48:2165-2171.
    • (1991) Life Sci , vol.48 , pp. 2165-2171
    • Chen, Z.R.1    Irvine, R.J.2    Somogyi, A.A.3    Bochner, F.4
  • 5
    • 0029930195 scopus 로고    scopus 로고
    • N-Cubylmethyl substituted morphinoids as novel narcotic antagonists
    • Cheng CY, Hsin L, Lin Y, Tao P, and Jong T (1996) N-Cubylmethyl substituted morphinoids as novel narcotic antagonists. Bioorg Med Chem 4:73-80.
    • (1996) Bioorg Med Chem , vol.4 , pp. 73-80
    • Cheng, C.Y.1    Hsin, L.2    Lin, Y.3    Tao, P.4    Jong, T.5
  • 6
    • 0028102911 scopus 로고
    • The influence of pharmacogenetics on opioid analgesia: Studies with codeine and oxycodone in the Sprague-Dawley/Dark Agouti rat model
    • Cleary J, Mikus G, Somogyi A, and Bochner F (1994) The influence of pharmacogenetics on opioid analgesia: studies with codeine and oxycodone in the Sprague-Dawley/Dark Agouti rat model. J Pharmacol Exp Ther 271:1528-1534.
    • (1994) J Pharmacol Exp Ther , vol.271 , pp. 1528-1534
    • Cleary, J.1    Mikus, G.2    Somogyi, A.3    Bochner, F.4
  • 8
    • 0023884310 scopus 로고
    • Bioactivation of the narcotic drug codeine in human liver is mediated by the polymorphic monooxygenase catalyzing debrisoquine 4-hydroxylation (cytochrome P-450 dbl/bufI)
    • Dayer P, Desmeules J, Leemann T, and Striberni R (1988) Bioactivation of the narcotic drug codeine in human liver is mediated by the polymorphic monooxygenase catalyzing debrisoquine 4-hydroxylation (cytochrome P-450 dbl/bufI). Biochem Biophys Res Commun 152:411-416.
    • (1988) Biochem Biophys Res Commun , vol.152 , pp. 411-416
    • Dayer, P.1    Desmeules, J.2    Leemann, T.3    Striberni, R.4
  • 9
    • 0035047220 scopus 로고    scopus 로고
    • Reactions of morphine derivatives with phenyliodo(III)diacetate (PIDA): Synthesis of new morphine analogs
    • Garadnay S, Herezegh S, Makleit T, Friedmann P, Riba P, and Fürst S (2001) Reactions of morphine derivatives with phenyliodo(III)diacetate (PIDA): synthesis of new morphine analogs. Curr Med Chem 8:621-626.
    • (2001) Curr Med Chem , vol.8 , pp. 621-626
    • Garadnay, S.1    Herezegh, S.2    Makleit, T.3    Friedmann, P.4    Riba, P.5    Fürst, S.6
  • 10
    • 0028178975 scopus 로고
    • Characterization and use of crude α-subunit preparations for quantitative immunoblotting of G-proteins
    • Gettys TW, Sheriff-Carter K, Moomaw J, Taylor IL, and Raymond JR (1994) Characterization and use of crude α-subunit preparations for quantitative immunoblotting of G-proteins. Anal Biochem 220:82-91.
    • (1994) Anal Biochem , vol.220 , pp. 82-91
    • Gettys, T.W.1    Sheriff-Carter, K.2    Moomaw, J.3    Taylor, I.L.4    Raymond, J.R.5
  • 11
    • 0032436459 scopus 로고    scopus 로고
    • Effects of blocking CYP2D6 on the pharmacokineties and pharmacodynamics of oxycodone
    • Heiskanen T, Olkkola KT, and Kalso E (1998) Effects of blocking CYP2D6 on the pharmacokineties and pharmacodynamics of oxycodone. Clin Pharmacol Ther 64:603-611.
    • (1998) Clin Pharmacol Ther , vol.64 , pp. 603-611
    • Heiskanen, T.1    Olkkola, K.T.2    Kalso, E.3
  • 12
    • 0020456973 scopus 로고
    • Light microscopic localization of brain opiate receptors: A general autoradiographic method which preserves tissue quality
    • Herkenham M and Pert CB (1982) Light microscopic localization of brain opiate receptors: a general autoradiographic method which preserves tissue quality. J Neurosci 2:1129-1149.
    • (1982) J Neurosci , vol.2 , pp. 1129-1149
    • Herkenham, M.1    Pert, C.B.2
  • 14
    • 0024787617 scopus 로고
    • Muscarinic acetylcholine receptor-stimulated binding of guanosine 5′-O-(3-thiotriphosphate) to guanine-nucleotide-binding proteins in cardiac membranes
    • Hilf G, Glerschik P, and Jakobs KH (1989) Muscarinic acetylcholine receptor-stimulated binding of guanosine 5′-O-(3-thiotriphosphate) to guanine-nucleotide-binding proteins in cardiac membranes. Eur J Biochem 186:725-731.
    • (1989) Eur J Biochem , vol.186 , pp. 725-731
    • Hilf, G.1    Glerschik, P.2    Jakobs, K.H.3
  • 15
    • 0020471133 scopus 로고
    • A novel metabolite of oxycodone in the urine of rabbits
    • Ishida T, Oguri K, and Yoshimura H (1982) A novel metabolite of oxycodone in the urine of rabbits. J Pharmacobiodyn 5:134-136.
    • (1982) J Pharmacobiodyn , vol.5 , pp. 134-136
    • Ishida, T.1    Oguri, K.2    Yoshimura, H.3
  • 16
    • 0030908875 scopus 로고    scopus 로고
    • Analgesia by dihydrocodeine is not due to formation of dihydromorphine: Evidence from nociceptive activity in rat thalamus
    • Jurna I, Komen W, Baldauf J, and Fleischer W (1997) Analgesia by dihydrocodeine is not due to formation of dihydromorphine: evidence from nociceptive activity in rat thalamus. J Pharmacol Exp Ther 281:1164-1170.
    • (1997) J Pharmacol Exp Ther , vol.281 , pp. 1164-1170
    • Jurna, I.1    Komen, W.2    Baldauf, J.3    Fleischer, W.4
  • 18
    • 0029054965 scopus 로고
    • Agonist-receptor efficacy. II. Agonist trafficking of receptor signals
    • Kenakin T (1995) Agonist-receptor efficacy. II. Agonist trafficking of receptor signals. Trends Pharmacol Sci 16:232-238.
    • (1995) Trends Pharmacol Sci , vol.16 , pp. 232-238
    • Kenakin, T.1
  • 19
    • 0030661633 scopus 로고    scopus 로고
    • Characterization of the human cytochrome P450 enzymes involved in the metabolism of dihydrocodeine
    • Kirkwood LC, Nation RL, and Somogyi AA (1997) Characterization of the human cytochrome P450 enzymes involved in the metabolism of dihydrocodeine. Br J Clin Pharmacol 44:549-555.
    • (1997) Br J Clin Pharmacol , vol.44 , pp. 549-555
    • Kirkwood, L.C.1    Nation, R.L.2    Somogyi, A.A.3
  • 20
    • 0033057632 scopus 로고    scopus 로고
    • Inhibitors of cytochrome P450 differentially modify discriminative-stimulus and antinociceptive effects of hydrocodone and hydromorphone in rhesus monkeys
    • Lelas S, Wegert S, Otton SV, Sellers EM, and France CP (1999) Inhibitors of cytochrome P450 differentially modify discriminative-stimulus and antinociceptive effects of hydrocodone and hydromorphone in rhesus monkeys. Drug Alcohol Depend 54:239-249.
    • (1999) Drug Alcohol Depend , vol.54 , pp. 239-249
    • Lelas, S.1    Wegert, S.2    Otton, S.V.3    Sellers, E.M.4    France, C.P.5
  • 21
    • 0028198174 scopus 로고
    • The antinociceptive potencies of oxycodone, noroxycodone and morphine after intracerebroventricular administration to rats
    • Leow KP and Smith MT (1994) The antinociceptive potencies of oxycodone, noroxycodone and morphine after intracerebroventricular administration to rats. Life Sci 54:1229-1236.
    • (1994) Life Sci , vol.54 , pp. 1229-1236
    • Leow, K.P.1    Smith, M.T.2
  • 22
    • 0032031040 scopus 로고    scopus 로고
    • mu Opioid receptor knockout in mice: Effects on ligand-induced analgesia and morphine lethality
    • Loh HH, Liu HC, Cavalli A, Yang W, Chen YF, and Wei LN (1998) mu Opioid receptor knockout in mice: effects on ligand-induced analgesia and morphine lethality. Brain Res Mol Brain Res 54:321-326.
    • (1998) Brain Res Mol Brain Res , vol.54 , pp. 321-326
    • Loh, H.H.1    Liu, H.C.2    Cavalli, A.3    Yang, W.4    Chen, Y.F.5    Wei, L.N.6
  • 23
    • 0033847006 scopus 로고    scopus 로고
    • Antagonism of delta(2)-opioid receptors by naltrindole-5′ -isothiocyanate attenuates heroin self-administration but not antinociception in rats
    • Martin TJ, Kim SA, Cannon DG, Sizemore GM, Bian D, Porreca F, and Smith JE (2000) Antagonism of delta(2)-opioid receptors by naltrindole-5′ -isothiocyanate attenuates heroin self-administration but not antinociception in rats. J Pharmacol Exp Ther 294:975-982.
    • (2000) J Pharmacol Exp Ther , vol.294 , pp. 975-982
    • Martin, T.J.1    Kim, S.A.2    Cannon, D.G.3    Sizemore, G.M.4    Bian, D.5    Porreca, F.6    Smith, J.E.7
  • 25
    • 0028836343 scopus 로고
    • Affinity profiles of morphine, codeine, dihydrocodeine and their glucuronides at opioid receptor subtypes
    • Mignat C, Wille U, and Ziegler A (1995) Affinity profiles of morphine, codeine, dihydrocodeine and their glucuronides at opioid receptor subtypes. Life Sci 56:793-799.
    • (1995) Life Sci , vol.56 , pp. 793-799
    • Mignat, C.1    Wille, U.2    Ziegler, A.3
  • 26
    • 0026030901 scopus 로고
    • Codeine O-demethylation: Rat strain differences and the effects of inhibitors
    • Mikus G, Somogyi AA, Bochner F, and Eichelbaum M (1991) Codeine O-demethylation: rat strain differences and the effects of inhibitors. Biochem Pharmacol 41:757-762.
    • (1991) Biochem Pharmacol , vol.41 , pp. 757-762
    • Mikus, G.1    Somogyi, A.A.2    Bochner, F.3    Eichelbaum, M.4
  • 27
    • 0037115025 scopus 로고    scopus 로고
    • Genetic dissociation of opiate tolerance and physical dependence in delta-opioid receptor-1 and preproenkephalin knock-out mice
    • Nitsche JF, Schuller AG, King MA, Zengh M, Pasternak GW, and Pintar JE (2002) Genetic dissociation of opiate tolerance and physical dependence in delta-opioid receptor-1 and preproenkephalin knock-out mice. J Neurosci 22:10906-10913.
    • (2002) J Neurosci , vol.22 , pp. 10906-10913
    • Nitsche, J.F.1    Schuller, A.G.2    King, M.A.3    Zengh, M.4    Pasternak, G.W.5    Pintar, J.E.6
  • 29
    • 0026749081 scopus 로고
    • The pharmacokinetics and metabolism of oxycodone after intramuscular and oral administration to healthy subjects
    • Poyhia R, Seppala T, Olkkola KT, and Kalso E (1992) The pharmacokinetics and metabolism of oxycodone after intramuscular and oral administration to healthy subjects. Br J Clin Pharmacol 33:617-621.
    • (1992) Br J Clin Pharmacol , vol.33 , pp. 617-621
    • Poyhia, R.1    Seppala, T.2    Olkkola, K.T.3    Kalso, E.4
  • 32
    • 0031017050 scopus 로고    scopus 로고
    • mu-Opioid receptor-stimulated guanosine-5′ -O-(gamma-thio)-triphosphate binding in rat thalamus and cultured cell lines: Signal transduction mechanisms underlying agonist efficacy
    • Selley DE, Sim LJ, Xiao R, Liu Q, and Childers SR (1997) mu-Opioid receptor-stimulated guanosine-5′-O-(gamma-thio)-triphosphate binding in rat thalamus and cultured cell lines: signal transduction mechanisms underlying agonist efficacy. Mol Pharmacol 51:87-96.
    • (1997) Mol Pharmacol , vol.51 , pp. 87-96
    • Selley, D.E.1    Sim, L.J.2    Xiao, R.3    Liu, Q.4    Childers, S.R.5
  • 33
    • 0029120593 scopus 로고
    • In vitro autoradiography of receptor-activated G proteins in rat brain by agonist-stimulated guanylyl 5′-[gamma-[35S]thio]-triphosphate binding
    • Sim LJ, Selley DE, and Childers SR (1995) In vitro autoradiography of receptor-activated G proteins in rat brain by agonist-stimulated guanylyl 5′-[gamma-[35S]thio]-triphosphate binding. Proc Natl Acad Sci USA 92:7242-7246.
    • (1995) Proc Natl Acad Sci USA , vol.92 , pp. 7242-7246
    • Sim, L.J.1    Selley, D.E.2    Childers, S.R.3
  • 34
    • 0031030042 scopus 로고    scopus 로고
    • Opiate receptor knockout mice define mu receptor roles in endogenous nociceptive responses and morphine-induced analgesia
    • Sora I, Takahashi N, Funada M, Ujike H, Revay RS, Donovan DM, Miner LL, and Uhl GR (1997) Opiate receptor knockout mice define mu receptor roles in endogenous nociceptive responses and morphine-induced analgesia. Proc Natl Acad Sci USA 94:1544-1549.
    • (1997) Proc Natl Acad Sci USA , vol.94 , pp. 1544-1549
    • Sora, I.1    Takahashi, N.2    Funada, M.3    Ujike, H.4    Revay, R.S.5    Donovan, D.M.6    Miner, L.L.7    Uhl, G.R.8
  • 35
    • 84986701061 scopus 로고
    • Action of bromocyanogen on hydroxycodeinone and dihydrohydroxycodeinone
    • Speyer E and Sarre K (1924) Action of bromocyanogen on hydroxycodeinone and dihydrohydroxycodeinone. Chem Ber 57:1427-1430.
    • (1924) Chem Ber , vol.57 , pp. 1427-1430
    • Speyer, E.1    Sarre, K.2
  • 36
    • 0031456986 scopus 로고    scopus 로고
    • Delta opioid modulation of the binding of guanosine-5′ -O-(3-[35S]thio)triphosphate to NG108-15 cell membranes: Characterization of agonist and inverse agonist effects
    • Szekeres PG and Traynor JR (1997) Delta opioid modulation of the binding of guanosine-5′-O-(3-[35S]thio)triphosphate to NG108-15 cell membranes: characterization of agonist and inverse agonist effects. J Pharmacol Exp Ther 283:1276-1284.
    • (1997) J Pharmacol Exp Ther , vol.283 , pp. 1276-1284
    • Szekeres, P.G.1    Traynor, J.R.2
  • 38
    • 0028986870 scopus 로고
    • 35S]thio)triphosphate binding to membranes from human neuroblastoma SH-SY5Y cells
    • 35S]thio)triphosphate binding to membranes from human neuroblastoma SH-SY5Y cells. Mol Pharmacol 47:848-854.
    • (1995) Mol Pharmacol , vol.47 , pp. 848-854
    • Traynor, J.R.1    Nahorski, S.R.2
  • 39
    • 0018765590 scopus 로고
    • Determination of oxycodone in plasma and identification of a major metabolite
    • Weinstein SH and Gaylord JC (1979) Determination of oxycodone in plasma and identification of a major metabolite. J Pharm Sci 68:527-528.
    • (1979) J Pharm Sci , vol.68 , pp. 527-528
    • Weinstein, S.H.1    Gaylord, J.C.2
  • 40
    • 0031839871 scopus 로고    scopus 로고
    • The visceral and somatic antinociceptive effects of dihydrocodeine and its metabolite, dihydromorphine. A cross-over study with extensive and quinidine-induced poor metabolizers
    • Wilder-Smith CH, Hufschmid E, and Thormann W (1998) The visceral and somatic antinociceptive effects of dihydrocodeine and its metabolite, dihydromorphine. A cross-over study with extensive and quinidine-induced poor metabolizers. Br J Clin Pharmacol 45:575-581.
    • (1998) Br J Clin Pharmacol , vol.45 , pp. 575-581
    • Wilder-Smith, C.H.1    Hufschmid, E.2    Thormann, W.3
  • 41
    • 0036897469 scopus 로고    scopus 로고
    • Expression, purification, biochemical characterization, and comparative function of human cytochrome P450 2D6.1, 2D6.2, 2D6.10 and 2D6.17 allelic isoforms
    • Yu A, Kneller BM, Rettie AE, and Haining RL (2002) Expression, purification, biochemical characterization, and comparative function of human cytochrome P450 2D6.1, 2D6.2, 2D6.10 and 2D6.17 allelic isoforms. J Pharmacol Exp Ther 303:1291-1300.
    • (2002) J Pharmacol Exp Ther , vol.303 , pp. 1291-1300
    • Yu, A.1    Kneller, B.M.2    Rettie, A.E.3    Haining, R.L.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.