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Volumn 375, Issue 1-2, 2009, Pages 48-54

Evaluation of the P-glycoprotein (Abcb1) affinity status of a series of morphine analogs: Comparative study with meperidine analogs to identify opioids with minimal P-glycoprotein interactions

Author keywords

Opioids; P glycoprotein; Transporters

Indexed keywords

6 DESOXYMORPHINE; ADENOSINE TRIPHOSPHATASE; CODEINE; ETORPHINE; GLYCOPROTEIN P; METHYL THEVINOL; MORPHINE; MORPHINE DERIVATIVE; N 2 METHYLPROPYL NORMEPERIDINE; N ALLYL NORMEPERIDINE; N BENZYL NORMEPERIDINE; N BENZYLCODEINE; N BUTYL NORMEPERIDINE; N CROTYL NORMEPERIDINE; N METHYLALLYL NORMEPERIDINE; N PHENYLBUTYL NORMEPERIDINE; N PHENYLPROPYL NORMEPERIDINE; N PROPYL NORMEPERIDINE; NALOXONE; NALTREXONE; NORPETHIDINE; OPIATE; OPIATE AGONIST; OPIATE ANTAGONIST; OXYMORPHONE; PETHIDINE; PETHIDINE DERIVATIVE; PIPERIDINE DERIVATIVE; THEVINONE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 67349278541     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2009.03.037     Document Type: Article
Times cited : (27)

References (41)
  • 2
    • 0017580705 scopus 로고
    • Comparisons of the analgesic effects of oral and intramuscular oxymorphone and of intramuscular oxymorphone and morphine in patients with cancer
    • Beaver W.T., Wallenstein S.L., Houde R.W., and Rogers A. Comparisons of the analgesic effects of oral and intramuscular oxymorphone and of intramuscular oxymorphone and morphine in patients with cancer. J. Clin. Pharmacol. 17 (1977) 186-198
    • (1977) J. Clin. Pharmacol. , vol.17 , pp. 186-198
    • Beaver, W.T.1    Wallenstein, S.L.2    Houde, R.W.3    Rogers, A.4
  • 3
    • 0014213108 scopus 로고
    • Novel analgesics and molecular rearrangements in the morphine-thebaine group. II. Alcohols derived from 6,14-endo-etheno- and 6,14-endo-ethanotetrahydrothebaine
    • Bentley K.W., Hardy D.G., and Meek B. Novel analgesics and molecular rearrangements in the morphine-thebaine group. II. Alcohols derived from 6,14-endo-etheno- and 6,14-endo-ethanotetrahydrothebaine. J. Am. Chem. Soc. 89 (1967) 3273-3280
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 3273-3280
    • Bentley, K.W.1    Hardy, D.G.2    Meek, B.3
  • 4
    • 0027221177 scopus 로고
    • Synthetic and natural opiates interact with P-glycoprotein in multidrug-resistant cells
    • Callaghan R., and Riordan J.R. Synthetic and natural opiates interact with P-glycoprotein in multidrug-resistant cells. J. Biol. Chem. 268 (1993) 16059-16064
    • (1993) J. Biol. Chem. , vol.268 , pp. 16059-16064
    • Callaghan, R.1    Riordan, J.R.2
  • 6
    • 0033051513 scopus 로고    scopus 로고
    • Enhanced antinociception of the model opioid peptide [d-penicillamine] enkephalin by P-glycoprotein modulation
    • Chen C., and Pollack G.M. Enhanced antinociception of the model opioid peptide [d-penicillamine] enkephalin by P-glycoprotein modulation. Pharm. Res. 16 (1999) 296-301
    • (1999) Pharm. Res. , vol.16 , pp. 296-301
    • Chen, C.1    Pollack, G.M.2
  • 7
    • 0002261078 scopus 로고
    • A method for determining loss of pain sensation
    • D'amour F., and Smith D. A method for determining loss of pain sensation. J. Pharmacol. Exp. Ther. 72 (1941) 74-79
    • (1941) J. Pharmacol. Exp. Ther. , vol.72 , pp. 74-79
    • D'amour, F.1    Smith, D.2
  • 8
    • 1642579542 scopus 로고    scopus 로고
    • Variable modulation of opioid brain uptake by P-glycoprotein in mice
    • Dagenais C., Graff C.L., and Pollack G.M. Variable modulation of opioid brain uptake by P-glycoprotein in mice. Biochem. Pharmacol. 67 (2004) 269-276
    • (2004) Biochem. Pharmacol. , vol.67 , pp. 269-276
    • Dagenais, C.1    Graff, C.L.2    Pollack, G.M.3
  • 9
    • 0027285344 scopus 로고
    • Dose-ranging study of oxycodone for chronic pain in advanced cancer
    • Glare P.A., and Walsh T.D. Dose-ranging study of oxycodone for chronic pain in advanced cancer. J. Clin. Oncol. 11 (1993) 973-978
    • (1993) J. Clin. Oncol. , vol.11 , pp. 973-978
    • Glare, P.A.1    Walsh, T.D.2
  • 10
    • 0027218689 scopus 로고
    • Biochemistry of multidrug resistance mediated by the multidrug transporter
    • Gottesman M.M., and Pastan I. Biochemistry of multidrug resistance mediated by the multidrug transporter. Annu. Rev. Biochem. 62 (1993) 385-427
    • (1993) Annu. Rev. Biochem. , vol.62 , pp. 385-427
    • Gottesman, M.M.1    Pastan, I.2
  • 12
    • 34748829961 scopus 로고    scopus 로고
    • Oxycodone induces overexpression of P-glycoprotein (ABCB1) and affects paclitaxel's tissue distribution in Sprague Dawley rats
    • Hassan H.E., Myers A.L., Lee I.J., Coop A., and Eddington N.D. Oxycodone induces overexpression of P-glycoprotein (ABCB1) and affects paclitaxel's tissue distribution in Sprague Dawley rats. J. Pharm. Sci. 96 (2007) 2494-2506
    • (2007) J. Pharm. Sci. , vol.96 , pp. 2494-2506
    • Hassan, H.E.1    Myers, A.L.2    Lee, I.J.3    Coop, A.4    Eddington, N.D.5
  • 13
    • 10044241598 scopus 로고    scopus 로고
    • Hepatobiliary disposition of the metabolically stable opioid peptide [D-Pen2, D-Pen5]-enkephalin (DPDPE): pharmacokinetic consequences of the interplay between multiple transport systems
    • Hoffmaster K.A., Zamek-Gliszczynski M.J., Pollack G.M., and Brouwer K.L. Hepatobiliary disposition of the metabolically stable opioid peptide [D-Pen2, D-Pen5]-enkephalin (DPDPE): pharmacokinetic consequences of the interplay between multiple transport systems. J. Pharmacol. Exp. Ther. 311 (2004) 1203-1210
    • (2004) J. Pharmacol. Exp. Ther. , vol.311 , pp. 1203-1210
    • Hoffmaster, K.A.1    Zamek-Gliszczynski, M.J.2    Pollack, G.M.3    Brouwer, K.L.4
  • 14
    • 0018178770 scopus 로고
    • Studies in the (+)-morphinan series. 5. Synthesis and biological properties of (+)-naloxone
    • Iijima I., Minamikawa J., Jacobson A.E., Brossi A., and Rice K.C. Studies in the (+)-morphinan series. 5. Synthesis and biological properties of (+)-naloxone. J. Med. Chem. 21 (1978) 398-400
    • (1978) J. Med. Chem. , vol.21 , pp. 398-400
    • Iijima, I.1    Minamikawa, J.2    Jacobson, A.E.3    Brossi, A.4    Rice, K.C.5
  • 15
    • 33846910647 scopus 로고
    • Compounds related to pethidine-IV. New general chemical methods of increasing the analgesic activity of pethidine
    • Janssen P.A., and Eddy N.B. Compounds related to pethidine-IV. New general chemical methods of increasing the analgesic activity of pethidine. J. Med. Pharm. Chem. 2 (1960) 31-45
    • (1960) J. Med. Pharm. Chem. , vol.2 , pp. 31-45
    • Janssen, P.A.1    Eddy, N.B.2
  • 16
    • 0029938602 scopus 로고    scopus 로고
    • Cyclosporin A treatment induces overexpression of P-glycoprotein in the kidney and other tissues
    • Jette L., Beaulieu E., Leclerc J.M., and Beliveau R. Cyclosporin A treatment induces overexpression of P-glycoprotein in the kidney and other tissues. Am. J. Physiol. 270 (1996) F756-765
    • (1996) Am. J. Physiol. , vol.270
    • Jette, L.1    Beaulieu, E.2    Leclerc, J.M.3    Beliveau, R.4
  • 17
    • 6344291034 scopus 로고    scopus 로고
    • Use of loperamide as a phenotypic probe of mdr1a status in CF-1 mice
    • Kalvass J.C., Graff C.L., and Pollack G.M. Use of loperamide as a phenotypic probe of mdr1a status in CF-1 mice. Pharm. Res. 21 (2004) 1867-1870
    • (2004) Pharm. Res. , vol.21 , pp. 1867-1870
    • Kalvass, J.C.1    Graff, C.L.2    Pollack, G.M.3
  • 19
    • 0031946026 scopus 로고    scopus 로고
    • Effect of GF120918, a potent P-glycoprotein inhibitor, on morphine pharmacokinetics and pharmacodynamics in the rat
    • Letrent S.P., Pollack G.M., Brouwer K.R., and Brouwer K.L. Effect of GF120918, a potent P-glycoprotein inhibitor, on morphine pharmacokinetics and pharmacodynamics in the rat. Pharm. Res. 15 (1998) 599-605
    • (1998) Pharm. Res. , vol.15 , pp. 599-605
    • Letrent, S.P.1    Pollack, G.M.2    Brouwer, K.R.3    Brouwer, K.L.4
  • 20
    • 0033060742 scopus 로고    scopus 로고
    • Effects of a potent and specific P-glycoprotein inhibitor on the blood-brain barrier distribution and antinociceptive effect of morphine in the rat
    • Letrent S.P., Pollack G.M., Brouwer K.R., and Brouwer K.L. Effects of a potent and specific P-glycoprotein inhibitor on the blood-brain barrier distribution and antinociceptive effect of morphine in the rat. Drug Metab. Dispos. 27 (1999) 827-834
    • (1999) Drug Metab. Dispos. , vol.27 , pp. 827-834
    • Letrent, S.P.1    Pollack, G.M.2    Brouwer, K.R.3    Brouwer, K.L.4
  • 22
    • 0037457793 scopus 로고    scopus 로고
    • Drug-drug interaction mediated by inhibition and induction of P-glycoprotein
    • Lin J.H. Drug-drug interaction mediated by inhibition and induction of P-glycoprotein. Adv. Drug Deliv. Rev. 55 (2003) 53-81
    • (2003) Adv. Drug Deliv. Rev. , vol.55 , pp. 53-81
    • Lin, J.H.1
  • 23
    • 0037229942 scopus 로고    scopus 로고
    • Role of P-glycoprotein in pharmacokinetics: clinical implications
    • Lin J.H., and Yamazaki M. Role of P-glycoprotein in pharmacokinetics: clinical implications. Clin. Pharmacokinet. 42 (2003) 59-98
    • (2003) Clin. Pharmacokinet. , vol.42 , pp. 59-98
    • Lin, J.H.1    Yamazaki, M.2
  • 25
    • 33846902630 scopus 로고    scopus 로고
    • Opioids and efflux transporters. Part 1: P-Glycoprotein substrate activity of N-substituted analogs of meperidine
    • Mercer S.L., Hassan H.E., Cunningham C.W., Eddington N.D., and Coop A. Opioids and efflux transporters. Part 1: P-Glycoprotein substrate activity of N-substituted analogs of meperidine. Bioorg. Med. Chem. Lett. 17 (2007) 1160-1162
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 1160-1162
    • Mercer, S.L.1    Hassan, H.E.2    Cunningham, C.W.3    Eddington, N.D.4    Coop, A.5
  • 26
    • 0033810893 scopus 로고    scopus 로고
    • Incomplete, asymmetric, and route-dependent cross-tolerance between oxycodone and morphine in the Dark Agouti rat
    • Nielsen C.K., Ross F.B., and Smith M.T. Incomplete, asymmetric, and route-dependent cross-tolerance between oxycodone and morphine in the Dark Agouti rat. J. Pharmacol. Exp. Ther. 295 (2000) 91-99
    • (2000) J. Pharmacol. Exp. Ther. , vol.295 , pp. 91-99
    • Nielsen, C.K.1    Ross, F.B.2    Smith, M.T.3
  • 27
    • 67349083402 scopus 로고
    • Comparative studies of 6-substituted delta 6-desoxymorphines and morphine with special reference to 6-methyl-delta6-desoxymorphine
    • Orahovats P.D., Winter C.A., Lehman E.G., and Flataker L. Comparative studies of 6-substituted delta 6-desoxymorphines and morphine with special reference to 6-methyl-delta6-desoxymorphine. J. Pharmacol. Exp. Ther. 114 (1955) 100-109
    • (1955) J. Pharmacol. Exp. Ther. , vol.114 , pp. 100-109
    • Orahovats, P.D.1    Winter, C.A.2    Lehman, E.G.3    Flataker, L.4
  • 29
    • 0030926727 scopus 로고    scopus 로고
    • Methods to compare dissolution profiles and a rationale for wide dissolution specifications for metoprolol tartrate tablets
    • Polli J.E., Rekhi G.S., Augsburger L.L., and Shah V.P. Methods to compare dissolution profiles and a rationale for wide dissolution specifications for metoprolol tartrate tablets. J. Pharm. Sci. 86 (1997) 690-700
    • (1997) J. Pharm. Sci. , vol.86 , pp. 690-700
    • Polli, J.E.1    Rekhi, G.S.2    Augsburger, L.L.3    Shah, V.P.4
  • 31
    • 0001544822 scopus 로고
    • Δ7 and Δ8-desoxycodeine
    • Rapoport H., and Bonner R. Δ7 and Δ8-desoxycodeine. J. Am. Chem. Soc. 73 (1951) 2872-2876
    • (1951) J. Am. Chem. Soc. , vol.73 , pp. 2872-2876
    • Rapoport, H.1    Bonner, R.2
  • 32
    • 0018764468 scopus 로고
    • Deoxymorphines: role of the phenolic hydroxyl in antinociception and opiate receptor interactions
    • Reden J., Reich M.F., Rice K.C., Jacobson A.E., Brossi A., Streaty R.A., and Klee W.A. Deoxymorphines: role of the phenolic hydroxyl in antinociception and opiate receptor interactions. J. Med. Chem. 22 (1979) 256-259
    • (1979) J. Med. Chem. , vol.22 , pp. 256-259
    • Reden, J.1    Reich, M.F.2    Rice, K.C.3    Jacobson, A.E.4    Brossi, A.5    Streaty, R.A.6    Klee, W.A.7
  • 33
    • 0033968760 scopus 로고    scopus 로고
    • Co-administration of sub-antinociceptive doses of oxycodone and morphine produces marked antinociceptive synergy with reduced CNS side-effects in rats
    • Ross F.B., Wallis S.C., and Smith M.T. Co-administration of sub-antinociceptive doses of oxycodone and morphine produces marked antinociceptive synergy with reduced CNS side-effects in rats. Pain 84 (2000) 421-428
    • (2000) Pain , vol.84 , pp. 421-428
    • Ross, F.B.1    Wallis, S.C.2    Smith, M.T.3
  • 34
    • 0029892497 scopus 로고    scopus 로고
    • P-glycoprotein in the blood-brain barrier of mice influences the brain penetration and pharmacological activity of many drugs
    • Schinkel A.H., Wagenaar E., Mol C.A., and van Deemter L. P-glycoprotein in the blood-brain barrier of mice influences the brain penetration and pharmacological activity of many drugs. J. Clin. Invest. 97 (1996) 2517-2524
    • (1996) J. Clin. Invest. , vol.97 , pp. 2517-2524
    • Schinkel, A.H.1    Wagenaar, E.2    Mol, C.A.3    van Deemter, L.4
  • 35
    • 0028825399 scopus 로고
    • Absence of the mdr1a P-Glycoprotein in mice affects tissue distribution and pharmacokinetics of dexamethasone, digoxin, and cyclosporin A
    • Schinkel A.H., Wagenaar E., van Deemter L., Mol C.A., and Borst P. Absence of the mdr1a P-Glycoprotein in mice affects tissue distribution and pharmacokinetics of dexamethasone, digoxin, and cyclosporin A. J. Clin. Invest. 96 (1995) 1698-1705
    • (1995) J. Clin. Invest. , vol.96 , pp. 1698-1705
    • Schinkel, A.H.1    Wagenaar, E.2    van Deemter, L.3    Mol, C.A.4    Borst, P.5
  • 36
    • 1242349778 scopus 로고    scopus 로고
    • Effects of ABCB1 (multidrug resistance transporter) gene mutations on disposition and central nervous effects of loperamide in healthy volunteers
    • Skarke C., Jarrar M., Schmidt H., Kauert G., Langer M., Geisslinger G., and Lotsch J. Effects of ABCB1 (multidrug resistance transporter) gene mutations on disposition and central nervous effects of loperamide in healthy volunteers. Pharmacogenetics 13 (2003) 651-660
    • (2003) Pharmacogenetics , vol.13 , pp. 651-660
    • Skarke, C.1    Jarrar, M.2    Schmidt, H.3    Kauert, G.4    Langer, M.5    Geisslinger, G.6    Lotsch, J.7
  • 37
    • 0034016617 scopus 로고    scopus 로고
    • Opiate-induced analgesia is increased and prolonged in mice lacking P-glycoprotein
    • Thompson S.J., Koszdin K., and Bernards C.M. Opiate-induced analgesia is increased and prolonged in mice lacking P-glycoprotein. Anesthesiology 92 (2000) 1392-1399
    • (2000) Anesthesiology , vol.92 , pp. 1392-1399
    • Thompson, S.J.1    Koszdin, K.2    Bernards, C.M.3
  • 39
    • 0019978757 scopus 로고
    • Antinociceptive activity and toxicity of meperidine and normeperidine in mice
    • Umans J.G., and Inturrisi C.E. Antinociceptive activity and toxicity of meperidine and normeperidine in mice. J. Pharmacol. Exp. Ther. 223 (1982) 203-206
    • (1982) J. Pharmacol. Exp. Ther. , vol.223 , pp. 203-206
    • Umans, J.G.1    Inturrisi, C.E.2
  • 40
    • 0036206856 scopus 로고    scopus 로고
    • Interaction of morphine, fentanyl, sufentanil, alfentanil, and loperamide with the efflux drug transporter P-glycoprotein
    • Wandel C., Kim R., Wood M., and Wood A. Interaction of morphine, fentanyl, sufentanil, alfentanil, and loperamide with the efflux drug transporter P-glycoprotein. Anesthesiology 96 (2002) 913-920
    • (2002) Anesthesiology , vol.96 , pp. 913-920
    • Wandel, C.1    Kim, R.2    Wood, M.3    Wood, A.4
  • 41
    • 0033844780 scopus 로고    scopus 로고
    • Morphine antinociception is enhanced in mdr1a gene-deficient mice
    • Zong J., and Pollack G.M. Morphine antinociception is enhanced in mdr1a gene-deficient mice. Pharm. Res. 17 (2000) 749-753
    • (2000) Pharm. Res. , vol.17 , pp. 749-753
    • Zong, J.1    Pollack, G.M.2


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