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Original Research

Combining rimonabant and fentanyl in a single entity: preparation and pharmacological results

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Pages 263-277 | Published online: 20 Feb 2014

References

  • Manzanares J Corchero J Romero J Fernandez-Ruiz JJ Ramos JA Fuentes JA Pharmacological and biochemical interactions between opioids and cannabinoids Trends Pharmacol Sci 1999 20 7 287 294 10390647
  • Vigano D Rubino T Parolaro D Molecular and cellular basis of cannabinoid and opioid interactions Pharmacol Biochem Behav 2005 81 2 360 368 15927245
  • Abrams DI Couey P Shade SB Kelly ME Benowitz NL Cannabinoid-opioid interaction in chronic pain Clin Pharmacol Ther 2011 90 6 844 851 22048225
  • Maldonado R Berrendero F Endogenous cannabinoid and opioid systems and their role in nicotine addiction Curr Drug Targets 2010 11 4 440 449 20017727
  • Christie MJ Opioid and cannabinoid receptors: friends with benefits or just close friends? Br J Pharmacol 2006 148 4 385 386 16682965
  • Trang T Sutak M Jhamandas K Involvement of cannabinoid (CB1)-receptors in the development and maintenance of opioid tolerance Neuroscience 2007 146 3 1275 1288 17395382
  • Scavone JL Sterling RC Van Bockstaele EJ Cannabinoid and opioid interactions: Implications for opiate dependence and withdrawal Neuroscience 2013 248 637 654 23624062
  • Morphy R Rankovic Z Designing multiple ligands – medicinal chemistry strategies and challenges Curr Pharm Des 2009 15 6 587 600 19199984
  • Shonberg J Scammells PJ Capuano B Design strategies for bivalent ligands targeting GPCRs Chem Med Chem 2011 6 6 963 974 21520422
  • Davis MP Fentanyl for breakthrough pain: a systematic review Expert Rev Neurother 2011 11 8 1197 1216 21797660
  • Jagerovic N Fernandez-Fernandez C Goya P CB1 cannabinoid antagonists: structure-activity relationships and potential therapeutic applications Curr Top Med Chem 2008 8 3 205 230 18289089
  • Christopoulou FD Kiortsis DN An overview of the metabolic effects of rimonabant in randomized controlled trials: potential for other cannabinoid 1 receptor blockers in obesity J Clin Pharm Ther 2011 36 1 10 18 21198716
  • Montero A Goya P Jagerovic N Guanidinium and aminoimidazolinium derivatives of N-(4-piperidyl)propanamides as potential ligands for mu opioid and I2-imidazoline receptors: synthesis and pharmacological screening Bioorg Med Chem 2002 10 4 1009 1018 11836109
  • Dardonville C Fernandez-Fernandez C Gibbons SL Synthesis and pharmacological studies of new hybrid derivatives of fentanyl active at the mu-opioid receptor and I-2-imidazoline binding sites Bioorg Med Chem 2006 14 19 6570 6580 16797997
  • Thomas BF Francisco MEY Seltzman HH Synthesis of long-chain amide analogs of the cannabinoid CB1 receptor antagonist N-(piperidinyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-py razole-3-carboxamide (SR141716) with unique binding selectivities and pharmacological activities Bioorg Med Chem 2005 13 18 5463 5474 15994087
  • Fernandez-Fernandez C Decara J Bermúdez-Silva FJ Description of a bivalent cannabinoid ligand with hypophagic properties Arch Pharm 2013 346 3 171 179
  • Sasmal PK Reddy DS Talwar R Novel pyrazole-3-carboxamide derivatives as cannabinoid-1 (CB1) antagonists: journey from non-polar to polar amides Bioorg Med Chem Lett 2011 21 1 562 568 21075633
  • Dardonville C Jagerovic N Callado LF Meana JJ Fentanyl derivatives bearing aliphatic alkaneguanidinium moieties: a new series of hybrid molecules with significant binding affinity for mu-opioid receptors and I2-imidazoline binding sites Bioorg Med Chem Lett 2004 14 2 491 493 14698188
  • Krishnamurthy M Li W Moore BM2nd Synthesis, biological evaluation, and structural studies on N1 and C5 substituted cycloalkyl analogues of the pyrazole class of CB1 and CB2 ligands Bioorg Med Chem 2004 12 2 393 404
  • De Jesus ML Salles J Meana JJ Callado LF Characterization of CB1 cannabinoid receptor immunoreactivity in postmortem human brain homogenates Neuroscience 2006 140 2 635 643 16563642
  • Cumella J Hernandez-Folgado L Giron R Chromenopyrazoles: non-psychoactive and selective CB1 cannabinoid agonists with peripheral antinociceptive properties ChemMedChem 2012 7 3 452 463 22302767
  • Gonzalez-Maeso J Rodriguez-Puertas R Gabilondo AM Meana JJ Characterization of receptor-mediated [35S]GTPgammaS binding to cortical membranes from postmortem human brain Eur J Pharmacol 2000 390 1–2 25 36 10708703
  • Pertwee RG The ring test: a quantitative method for assessing the ‘cataleptic’ effect of cannabis in mice Br J Pharmacol 1972 46 4 753 763 4655271
  • Serra S Carai MA Brunetti G The cannabinoid receptor antagonist SR 141716 prevents acquisition of drinking behavior in alcohol-preferring rats Eur J Pharmacol 2001 430 2–3 369 371 11711056
  • Erdozain AM Diez-Alarcia R Meana JJ Callado LF The inverse agonist effect of rimonabant on G protein activation is not mediated by the cannabinoid CB1 receptor: evidence from postmortem human brain Biochem Pharmacol 2012 83 2 260 268 22093909
  • Rowland NE Mukherjee M Robertson K Effects of the cannabinoid receptor antagonist SR 141716, alone and in combination with dexfenfluramine or naloxone, on food intake in rats Psychopharmacology 2001 159 1 111 116 11797078
  • Robledo P Berrendero F Ozaita A Maldonado R Advances in the field of cannabinoid-opioid cross-talk Addict Biol 2008 13 2 213 224 18482431
  • Tallett AJ Blundell JE Rodgers RJ Effects of acute low-dose combined treatment with naloxone and AM 251 on food intake, feeding behaviour and weight gain in rats Pharmacol Biochem Behav 2009 91 3 358 366 18755211
  • Wright FL Rodgers RJ Low dose naloxone attenuates the pruritic but not anorectic response to rimonabant in male rats Psychopharmacology 2013 226 2 415 431
  • Pertwee RG Stevenson LA Elrick DB Mechoulam R Corbett AD Inhibitory effects of certain enantiomeric cannabinoids in the mouse vas deferens and the myenteric plexus preparation of guinea-pig small intestine Br J Pharmacol 1992 105 4 980 984 1324060
  • Heyser CJ Moc K Koob GF Effects of naltrexone alone and in combination with acamprosate on the alcohol deprivation effect in rats Neuropsychopharmacology 2003 28 8 1463 1471 12700689
  • Lopez-Moreno JA Gonzalez-Cuevas G Rodriguez de Fonseca F Navarro M Long-lasting increase of alcohol relapse by the cannabinoid receptor agonist WIN 55,212-2 during alcohol deprivation J Neurosci 2004 24 38 8245 8252 15385608
  • Bowen JP Guner OF A perspective on quantum mechanics calculations in ADMET predictions Curr Top Med Chem 2013 13 11 1257 1272 23675934
  • Lipinski CA Lombardo F Dominy BW Feeney PJ Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv Drug Deliv Rev 2001 46 1–3 3 26 11259830
  • Jorgensen WL Duffy EM Prediction of drug solubility from structure Adv Drug Deliv Rev 2002 54 3 355 366 11922952
  • Le Naour M Akgun E Yekkirala A Bivalent ligands that target mu opioid (MOP) and cannabinoid1 (CB) receptors are potent analgesics devoid of tolerance J Med Chem 2013 56 13 5505 5513 23734559