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Volumn 809, Issue , 2017, Pages 111-121

New opioid receptor antagonist: Naltrexone-14-O-sulfate synthesis and pharmacology

Author keywords

Isolated organs; Mouse tail flick assay; Naltrexone 14 O sulfate; Opioid receptor binding

Indexed keywords

DELTA OPIATE RECEPTOR; KAPPA OPIATE RECEPTOR; MORPHINE; MU OPIATE RECEPTOR; NALOXONE; NALTREXONE; NALTREXONE 14 O SULFATE; OPIATE AGONIST; UNCLASSIFIED DRUG; ANALGESIC AGENT; NALTREXONE-14-O-SULFATE; NARCOTIC ANTAGONIST; OPIATE RECEPTOR;

EID: 85020107892     PISSN: 00142999     EISSN: 18790712     Source Type: Journal    
DOI: 10.1016/j.ejphar.2017.05.024     Document Type: Article
Times cited : (6)

References (51)
  • 1
    • 0030682389 scopus 로고    scopus 로고
    • Etorphines: mu-opioid receptor-selective antinociception and low physical dependence capacity
    • Aceto, M.D., Harris, L.S., Bowman, E.R., Etorphines: mu-opioid receptor-selective antinociception and low physical dependence capacity. Eur. J. Pharmacol. 338 (1997), 215–223.
    • (1997) Eur. J. Pharmacol. , vol.338 , pp. 215-223
    • Aceto, M.D.1    Harris, L.S.2    Bowman, E.R.3
  • 5
    • 0030611354 scopus 로고    scopus 로고
    • Met5-enkephalin-Arg6-Phe7, an endogenous neuropeptide, binds to multiple opioid and nonopioid sites in rat brain
    • Benyhe, S., Farkas, J., Tóth, G., Wollemann, M., Met5-enkephalin-Arg6-Phe7, an endogenous neuropeptide, binds to multiple opioid and nonopioid sites in rat brain. J. Neurosci. Res. 48 (1997), 249–258.
    • (1997) J. Neurosci. Res. , vol.48 , pp. 249-258
    • Benyhe, S.1    Farkas, J.2    Tóth, G.3    Wollemann, M.4
  • 6
    • 0021884842 scopus 로고
    • The use of quaternary narcotic antagonists in opiate research
    • Brown, D.R., Goldberg, L.I., The use of quaternary narcotic antagonists in opiate research. Neuropharmacology 24 (1985), 181–191.
    • (1985) Neuropharmacology , vol.24 , pp. 181-191
    • Brown, D.R.1    Goldberg, L.I.2
  • 7
    • 0027202213 scopus 로고
    • Molecular cloning and functional expression of a mu-opioid receptor from rat brain
    • Chen, Y., Mestek, A., Liu, J., Hurley, J.A., Yu, L., Molecular cloning and functional expression of a mu-opioid receptor from rat brain. Mol. Pharmacol. 44 (1993), 8–12.
    • (1993) Mol. Pharmacol. , vol.44 , pp. 8-12
    • Chen, Y.1    Mestek, A.2    Liu, J.3    Hurley, J.A.4    Yu, L.5
  • 8
    • 0029048267 scopus 로고
    • Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception
    • Codd, E.E., Shank, R.P., Schupsky, J.J., Raffa, R.B., Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. J. Pharmacol. Exp. Ther. 274 (1995), 1263–1270.
    • (1995) J. Pharmacol. Exp. Ther. , vol.274 , pp. 1263-1270
    • Codd, E.E.1    Shank, R.P.2    Schupsky, J.J.3    Raffa, R.B.4
  • 9
    • 79960031490 scopus 로고    scopus 로고
    • Clinical inquiries. What are the adverse effects of prolonged opioid use in patients with chronic pain?
    • Edgerton, L., Loven, B., Clinical inquiries. What are the adverse effects of prolonged opioid use in patients with chronic pain?. J. Fam. Pract. 60 (2011), 288–289.
    • (2011) J. Fam. Pract. , vol.60 , pp. 288-289
    • Edgerton, L.1    Loven, B.2
  • 10
    • 0027050144 scopus 로고
    • Cloning of a delta opioid receptor by functional expression
    • Evans, C.J., Keith, D.E., Morrison, H., Magendzo, K., Edwards, R.H., Cloning of a delta opioid receptor by functional expression. Science 58 (1992), 1952–1955.
    • (1992) Science , vol.58 , pp. 1952-1955
    • Evans, C.J.1    Keith, D.E.2    Morrison, H.3    Magendzo, K.4    Edwards, R.H.5
  • 11
    • 0033555286 scopus 로고    scopus 로고
    • Transmitters involved in antinociception in the spinal cord
    • Fürst, S., Transmitters involved in antinociception in the spinal cord. Brain Res. Bull. 48 (1999), 129–141.
    • (1999) Brain Res. Bull. , vol.48 , pp. 129-141
    • Fürst, S.1
  • 13
    • 0030931722 scopus 로고    scopus 로고
    • Butorphanol-mediated antinociception in mice: partial agonist effects and mu receptor involvement
    • Garner, H.R., Burke, T.F., Lawhorn, C.D., Stoner, J.M., Wessinger, W.D., Butorphanol-mediated antinociception in mice: partial agonist effects and mu receptor involvement. J. Pharmacol. Exp. Ther. 282 (1997), 1253–1261.
    • (1997) J. Pharmacol. Exp. Ther. , vol.282 , pp. 1253-1261
    • Garner, H.R.1    Burke, T.F.2    Lawhorn, C.D.3    Stoner, J.M.4    Wessinger, W.D.5
  • 14
    • 67349119441 scopus 로고    scopus 로고
    • Opioid receptors in the gastrointestinal tract
    • Holzer, P., Opioid receptors in the gastrointestinal tract. Regul. Pept. 155 (2009), 11–17.
    • (2009) Regul. Pept. , vol.155 , pp. 11-17
    • Holzer, P.1
  • 15
    • 84878309097 scopus 로고    scopus 로고
    • Peripheral antinociceptive efficacy and potency of a novel opioid compound 14-O-MeM6SU in comparison to known peptide and non-peptide opioid agonists in a rat model of inflammatory pain
    • Khalefa, B.I., Mousa, S.A., Shaqura, M., Lackó, E., Hosztafi, S., Riba, P., Schäfer, M., Ferdinandy, P., Fürst, S., Al-Khrasani, M., Peripheral antinociceptive efficacy and potency of a novel opioid compound 14-O-MeM6SU in comparison to known peptide and non-peptide opioid agonists in a rat model of inflammatory pain. Eur. J. Pharmacol. 713 (2013), 54–57.
    • (2013) Eur. J. Pharmacol. , vol.713 , pp. 54-57
    • Khalefa, B.I.1    Mousa, S.A.2    Shaqura, M.3    Lackó, E.4    Hosztafi, S.5    Riba, P.6    Schäfer, M.7    Ferdinandy, P.8    Fürst, S.9    Al-Khrasani, M.10
  • 16
    • 28544453487 scopus 로고    scopus 로고
    • New achievements and pharmacotherapeutic approaches in the treatment of alcohol dependence
    • Kiefer, F., Mann, K., New achievements and pharmacotherapeutic approaches in the treatment of alcohol dependence. Eur. J. Pharmacol. 526 (2005), 163–171.
    • (2005) Eur. J. Pharmacol. , vol.526 , pp. 163-171
    • Kiefer, F.1    Mann, K.2
  • 17
    • 0027052952 scopus 로고
    • The delta-opioid receptor: isolation of a cDNA by expression cloning and pharmacological characterization
    • Kieffer, B.L., Befort, K., Gaveriaux-Ruff, C., Hirth, C.G., The delta-opioid receptor: isolation of a cDNA by expression cloning and pharmacological characterization. Proc. Natl. Acad. Sci. USA 89 (1992), 12048–12052.
    • (1992) Proc. Natl. Acad. Sci. USA , vol.89 , pp. 12048-12052
    • Kieffer, B.L.1    Befort, K.2    Gaveriaux-Ruff, C.3    Hirth, C.G.4
  • 19
    • 0014298035 scopus 로고
    • Kinetic parameters of narcotic agonists and antagonists, with particular reference to N-allylnoroxymorphone (naloxone)
    • Kosterlitz, H.W., Watt, A.J., Kinetic parameters of narcotic agonists and antagonists, with particular reference to N-allylnoroxymorphone (naloxone). Br. J. Pharmacol. Chemother. 33 (1968), 266–276.
    • (1968) Br. J. Pharmacol. Chemother. , vol.33 , pp. 266-276
    • Kosterlitz, H.W.1    Watt, A.J.2
  • 25
    • 0037036212 scopus 로고    scopus 로고
    • Naloxone methiodide reverses opioid-induced respiratory depression and analgesia without withdrawal
    • Lewanowitsch, T., Irvine, R.J., Naloxone methiodide reverses opioid-induced respiratory depression and analgesia without withdrawal. Eur. J. Pharmacol. 445 (2002), 61–67.
    • (2002) Eur. J. Pharmacol. , vol.445 , pp. 61-67
    • Lewanowitsch, T.1    Irvine, R.J.2
  • 26
    • 0015623119 scopus 로고
    • Narcotic antagonists. 1. isomeric sulfate and acetate esters of naloxone (N-allylnoroxymorphone)
    • Linder, C., Fishman, J., Narcotic antagonists. 1. isomeric sulfate and acetate esters of naloxone (N-allylnoroxymorphone). J. Med. Chem. 16 (1973), 553–556.
    • (1973) J. Med. Chem. , vol.16 , pp. 553-556
    • Linder, C.1    Fishman, J.2
  • 27
    • 0028887626 scopus 로고
    • Opioid-receptor mRNA expression in the rat CNS: anatomical and functional implications
    • Mansour, A., Fox, C., Akil, H., Watson, S., Opioid-receptor mRNA expression in the rat CNS: anatomical and functional implications. Trends Neurosci. 18 (1995), 22–29.
    • (1995) Trends Neurosci. , vol.18 , pp. 22-29
    • Mansour, A.1    Fox, C.2    Akil, H.3    Watson, S.4
  • 28
    • 84964043722 scopus 로고    scopus 로고
    • Efficacy of methylnaltrexone for the treatment of opiod-induced constipation: a meta-analysis and systematic review
    • Mehta, N., O'Connell, K., Giambrone, G., Baqai, A., Diwan, S., Efficacy of methylnaltrexone for the treatment of opiod-induced constipation: a meta-analysis and systematic review. Postgrad. Med, 2016.
    • (2016) Postgrad. Med
    • Mehta, N.1    O'Connell, K.2    Giambrone, G.3    Baqai, A.4    Diwan, S.5
  • 31
    • 0027746813 scopus 로고
    • Antagonist effects of beta-funaltrexamine and naloxonazine on alfentanil-induced antinociception and muscle rigidity in the rat
    • Negus, S.S., Pasternak, G.W., Koob, G.F., Weinger, M.B., Antagonist effects of beta-funaltrexamine and naloxonazine on alfentanil-induced antinociception and muscle rigidity in the rat. J. Pharmacol. Exp. Ther., 264, 1993.
    • (1993) J. Pharmacol. Exp. Ther. , vol.264
    • Negus, S.S.1    Pasternak, G.W.2    Koob, G.F.3    Weinger, M.B.4
  • 32
    • 0028198507 scopus 로고
    • Binding characteristics of the novel highly selective delta agonist, [3H]IIe5,6deltorphin II
    • Nevin, S.T., Kabasakal, L., Otvös, F., Töth, G., Borsodi, A., Binding characteristics of the novel highly selective delta agonist, [3H]IIe5,6deltorphin II. Neuropeptides 26 (1994), 261–265.
    • (1994) Neuropeptides , vol.26 , pp. 261-265
    • Nevin, S.T.1    Kabasakal, L.2    Otvös, F.3    Töth, G.4    Borsodi, A.5
  • 33
    • 0025780114 scopus 로고
    • Opioid receptor labeling with the chloromethyl ketone derivative of [3H]Tyr-D-Ala-Gly-(Me)Phe-Gly-ol (DAMGO) II: covalent labeling of mu opioid binding site by 3H-Tyr-D-Ala-Gly-(Me)Phe chloromethyl ketone
    • Oktem, H.A., Moitra, J., Benyhe, S., Toth, G., Lajtha, A., Borsodi, A., Opioid receptor labeling with the chloromethyl ketone derivative of [3H]Tyr-D-Ala-Gly-(Me)Phe-Gly-ol (DAMGO) II: covalent labeling of mu opioid binding site by 3H-Tyr-D-Ala-Gly-(Me)Phe chloromethyl ketone. Life Sci. 48 (1991), 1763–1768.
    • (1991) Life Sci. , vol.48 , pp. 1763-1768
    • Oktem, H.A.1    Moitra, J.2    Benyhe, S.3    Toth, G.4    Lajtha, A.5    Borsodi, A.6
  • 34
    • 37549016836 scopus 로고    scopus 로고
    • Heterotrimeric G protein activation by G-protein-coupled receptors
    • Oldham, W.M., Hamm, H.E., Heterotrimeric G protein activation by G-protein-coupled receptors. Nat. Rev. Mol. Cell Biol. 9 (2008), 60–71.
    • (2008) Nat. Rev. Mol. Cell Biol. , vol.9 , pp. 60-71
    • Oldham, W.M.1    Hamm, H.E.2
  • 35
    • 0028965285 scopus 로고
    • Peripheral effects of naloxone in mice with acute diarrhea associated with intestinal inflammation
    • Pol, O., Planas, E., Puig, M.M., Peripheral effects of naloxone in mice with acute diarrhea associated with intestinal inflammation. J. Pharmacol. Exp. Ther. 272 (1995), 1271–1276.
    • (1995) J. Pharmacol. Exp. Ther. , vol.272 , pp. 1271-1276
    • Pol, O.1    Planas, E.2    Puig, M.M.3
  • 37
    • 77949908684 scopus 로고    scopus 로고
    • Naltrexone for the treatment of alcoholism: clinical findings, mechanisms of action, and pharmacogenetics
    • Ray, L.A., Chin, P.F., Miotto, K., Naltrexone for the treatment of alcoholism: clinical findings, mechanisms of action, and pharmacogenetics. CNS Neurol. Disord. Drug Targets 9 (2010), 13–22.
    • (2010) CNS Neurol. Disord. Drug Targets , vol.9 , pp. 13-22
    • Ray, L.A.1    Chin, P.F.2    Miotto, K.3
  • 38
    • 0017656699 scopus 로고
    • Differential behaviour of LPH-(61–91)-peptide in different model systems: comparison of the opioid activities of LPH-(61–91)-peptide and its fragments
    • Rónai, A.Z., Gráf, L., Székely, J.I., Dunai-Kovács, Z., Bajusz, S., Differential behaviour of LPH-(61–91)-peptide in different model systems: comparison of the opioid activities of LPH-(61–91)-peptide and its fragments. FEBS Lett. 74 (1977), 182–184.
    • (1977) FEBS Lett. , vol.74 , pp. 182-184
    • Rónai, A.Z.1    Gráf, L.2    Székely, J.I.3    Dunai-Kovács, Z.4    Bajusz, S.5
  • 39
    • 0021360975 scopus 로고
    • In vivo studies on spinal opiate receptor systems mediating antinociception. II. Pharmacological profiles suggesting a differential association of mu, delta and kappa receptors with visceral chemical and cutaneous thermal stimuli in the rat
    • Schmauss, C., Yaksh, T.L., In vivo studies on spinal opiate receptor systems mediating antinociception. II. Pharmacological profiles suggesting a differential association of mu, delta and kappa receptors with visceral chemical and cutaneous thermal stimuli in the rat. J. Pharmacol. Exp. Ther., 228, 1984.
    • (1984) J. Pharmacol. Exp. Ther. , vol.228
    • Schmauss, C.1    Yaksh, T.L.2
  • 40
    • 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, L.J., Selley, D.E., Childers, S.R., 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 (1995), 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
  • 41
    • 84860669844 scopus 로고    scopus 로고
    • Recent advances in the development of 14-alkoxy substituted morphinans as potent and safer opioid analgesics
    • Spetea, M., Schmidhammer, H., Recent advances in the development of 14-alkoxy substituted morphinans as potent and safer opioid analgesics. Curr. Med. Chem. 19 (2012), 2442–2457.
    • (2012) Curr. Med. Chem. , vol.19 , pp. 2442-2457
    • Spetea, M.1    Schmidhammer, H.2
  • 43
    • 0023220263 scopus 로고
    • Detailed analysis of heterogeneity of [3H]naloxone binding sites in rat brain synaptosomes
    • Szücs, M., Borsodi, A., Bogdány, A., Gaál, J., Batke, J., Tóth, G., Detailed analysis of heterogeneity of [3H]naloxone binding sites in rat brain synaptosomes. Neurochem. Res. 12 (1987), 581–587.
    • (1987) Neurochem. Res. , vol.12 , pp. 581-587
    • Szücs, M.1    Borsodi, A.2    Bogdány, A.3    Gaál, J.4    Batke, J.5    Tóth, G.6
  • 44
    • 0021137625 scopus 로고
    • Comparative antagonism by naltrexone and naloxone of mu, kappa, and delta agonists
    • Takemori, A.E., Portoghese, P.S., Comparative antagonism by naltrexone and naloxone of mu, kappa, and delta agonists. Eur. J. Pharmacol. 104 (1984), 101–104.
    • (1984) Eur. J. Pharmacol. , vol.104 , pp. 101-104
    • Takemori, A.E.1    Portoghese, P.S.2
  • 45
    • 0028986870 scopus 로고
    • Modulation by mu-opioid agonists of guanosine-5'-O-(3-[35S]thio)triphosphate binding to membranes from human neuroblastoma SH-SY5Y cells
    • Traynor, J.R., Nahorski, S.R., Modulation by mu-opioid agonists of guanosine-5'-O-(3-[35S]thio)triphosphate binding to membranes from human neuroblastoma SH-SY5Y cells. Mol. Pharmacol. 47 (1995), 848–854.
    • (1995) Mol. Pharmacol. , vol.47 , pp. 848-854
    • Traynor, J.R.1    Nahorski, S.R.2
  • 46
    • 0016110486 scopus 로고
    • The increased efficacy of narcotic antagonists induced by various narcotic analgesics
    • Tulunay, F.C., Takemori, A.E., The increased efficacy of narcotic antagonists induced by various narcotic analgesics. J. Pharmacol. Exp. Ther. 190 (1974), 395–400.
    • (1974) J. Pharmacol. Exp. Ther. , vol.190 , pp. 395-400
    • Tulunay, F.C.1    Takemori, A.E.2
  • 48
    • 0028172305 scopus 로고
    • In vivo apparent pA2 analysis for naltrexone antagonism of discriminative stimulus and analgesic effects of opiate agonists in rats
    • Walker, E.A., Makhay, M.M., House, J.D., Young, A.M., In vivo apparent pA2 analysis for naltrexone antagonism of discriminative stimulus and analgesic effects of opiate agonists in rats. J. Pharmacol. Exp. Ther., 271, 1994.
    • (1994) J. Pharmacol. Exp. Ther. , vol.271
    • Walker, E.A.1    Makhay, M.M.2    House, J.D.3    Young, A.M.4
  • 50
    • 0028930716 scopus 로고
    • Effects of methylnaltrexone on morphine-induced inhibition of contraction in isolated guinea-pig ileum and human intestine
    • Yuan, C.S., Foss, J.F., Moss, J., Effects of methylnaltrexone on morphine-induced inhibition of contraction in isolated guinea-pig ileum and human intestine. Eur. J. Pharmacol. 276 (1995), 107–111.
    • (1995) Eur. J. Pharmacol. , vol.276 , pp. 107-111
    • Yuan, C.S.1    Foss, J.F.2    Moss, J.3
  • 51
    • 84939896355 scopus 로고    scopus 로고
    • Methylnaltrexone: its pharmacological effects alone and effects on morphine in healthy volunteers
    • Zacny, J.P., Wroblewski, K., Coalson, D.W., Methylnaltrexone: its pharmacological effects alone and effects on morphine in healthy volunteers. Psychopharmacology 232 (2015), 63–73.
    • (2015) Psychopharmacology , vol.232 , pp. 63-73
    • Zacny, J.P.1    Wroblewski, K.2    Coalson, D.W.3


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