Analgesic activity and pharmacological characterization of N-[1-phenylpyrazol-3-yl]-N-[1-(2-phenethyl)-4-piperidyl] propenamide, a new opioid agonist acting peripherally

European Journal of Pharmacology

Volumn 595, Issue 1-3, 2008, Pages 22-29

  Goicoechea, Carlos ^a   Sánchez, Eva ^a   Cano, Carolina ^b   Jagerovic, Nadine ^b   Martín, Maria Isabel ^a  

^a UNIVERSIDAD REY JUAN CARLOS   (Spain)

^b CSIC   (Spain)

Author keywords

Analgesia; Dependence; Opioid; Peripheral effect; Tolerance

Indexed keywords

17 METHYLNALOXONE; FENTANYL; IQMF 4; MORPHINE; N (1 PHENYLPYRAZOL 3 YL) N [1 (2 PHENETHYL) 4 PIPERIDYL]PROPENAMIDE; NALOXONE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ANTAGONISM; DRUG EFFECT; DRUG POTENCY; DRUG TOLERABILITY; GUINEA PIG; HOT PLATE TEST; IN VITRO STUDY; IN VIVO STUDY; MALE; MOUSE; MYENTERIC PLEXUS; NONHUMAN; PRIORITY JOURNAL; WITHDRAWAL SYNDROME;

ADMINISTRATION, ORAL; ANALGESICS, OPIOID; ANIMALS; DISEASE MODELS, ANIMAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG TOLERANCE; FENTANYL; GUINEA PIGS; HEAT; ILEUM; INJECTIONS, INTRAPERITONEAL; INJECTIONS, INTRAVENTRICULAR; MALE; MICE; MORPHINE; MUSCLE CONTRACTION; MUSCLE, SMOOTH; NALOXONE; NARCOTIC ANTAGONISTS; OPIOID-RELATED DISORDERS; PAIN; PAIN MEASUREMENT; PAIN THRESHOLD; PIPERIDINES; PROPANE; QUATERNARY AMMONIUM COMPOUNDS; REACTION TIME; SUBSTANCE WITHDRAWAL SYNDROME; TIME FACTORS;

EID: 52049117377     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejphar.2008.07.052     Document Type: Article

References (33)

1. Abalo R., Vera G., Rivera A.J., and Martín M.I. Age-related changes in the gastrointestinal tract: a functional and immunohistochemical study in guinea-pig ileum. Life Sci. 80 26 (2007) 2436-2445
2. Alfaro M.J., Colado M.I., López F., and Martín M.I. Effect of clonidine, nimodipine and diltiazem on the in vitro opioid withdrawal response in the guinea-pig ileum. Br. J. Pharmacol. 101 (1990) 958-960
3. Al-Khrasani M., Spetea M., Friedmann T., Riba P., Király K., Schmidhammerb H., and Furst S. DAMGO and 6b-glycine substituted 14-O-methyloxymorphone but not morphine show peripheral, preemptive antinociception after systemic administration in a mouse visceral pain model and high intrinsic efficacy in the isolated rat vas deferens. Brain Res. Bull. 74 (2007) 369-375
4. Ambache N., Freeman M.A., and Hobbiger F. Localization of acetyl- and butyrylcholinesterases in the myenteric plexus and longitudinal muscle of the guinea-pig's ileum. J. Physiol. 200 (1969) 50-51P
5. Arias A., Feinn R., and Kranzler H.R. Association of an Asn40Asp (A118G) polymorphism in the mu-opioid receptor gene with substance dependence: a meta-analysis. Drug Alcohol Depend. 83 (2006) 262-268
6. Bileviciute-Ljungar I., Spetea M., Guo Y., Schutz J., Windisch P., and Schmidhammer H. Peripherally mediated antinociception of the m-opioid receptor agonist 2-[(4,5{alpha}-Epoxy-3-hydroxy-14beta-methoxy-17-methylmorphinan-6beta-yl) amino] acetic acid (HS-731) after subcutaneous and oral administration in rats with carrageenan-induced hindpaw inflammation. J. Pharmacol. Exp. Ther. 317 (2006) 220-227
7. Eisenberg E., McNicol E.D., and Carr D.B. Efficacy of mu-opioid agonists in the treatment of evoked neuropathic pain: systematic review of randomized controlled trials. Eur. J. Pain. 10 (2006) 667-676
8. Eisenberg R.M. Further studies on the acute dependence produced by morphine in opiate naive rats. Life Sci. 31 (1982) 1531-1540
9. Essawi M.Y.H. Fentanyl analogues with a modified propanamido group as potential affinity labels: synthesis and in vivo activity. Pharmazie 54 4 (1999) 307-308
10. Gebhart G.F., and Mitchell C.L. Further studies on the development of tolerance to the analgesic effect of morphine: the role played by the cylinder in the hot plate testing procedure. Arch. Int. Pharmacodyn. Ther. 191 (1971) 96-103
11. Gillan M.G., Kosterlitz H.W., Robson L.E., and Waterfiel A.A. The inhibitory effects of presynaptic alpha-adrenoceptor agonists on contractions of guinea-pig ileum and mouse vas deferens in the morphine-dependent and withdrawn states produced in vitro. Br. J. Pharmacol. 66 (1979) 601-608
12. Ginztler A.R. Substance P involvement in the expression of gut dependence on opiates. Brain Res. 182 (1980) 224-228
13. Girón R., Abalo R., Goicoechea C., Martín M.I., Callado L.F., Cano C., Goya P., and Jagerovic N. Synthesis and opioid activity of new fentanyl analogs. Life Sci. 71 (2002) 1023-1034
14. Ji Y., Murphy A.Z., and Traub R.J. Sex differences in morphine-induced analgesia of visceral pain are supraspinally and peripherally mediated. Am. J. Physiol., Regul. Integr. Comp. Physiol. 291 (2006) R307-R314
15. Kumar V., Guo D., Cassel J.A., Daubert J.D., Dehaven R.N., Dehaven-Hudkins D.L., Gauntner E.K., Gottshall S.L., Greiner S.L., Koblish M., Little P.J., Mansson E., and Maycock A.L. Synthesis and evaluation of novel peripherally restricted kappa-opioid receptor agonists. Bioorg. Med. Chem. Lett. 15 (2005) 1091-1095
16. Langford R., McKenna F., Ratcliffe S., Vojtassak J., and Richarz U. Transdermal fentanyl for improvement of pain and functioning in osteoarthritis: a randomized, placebo-controlled trial. Arthritis Rheum. 54 (2006) 1829-1837
17. Leslie F.M. Methods used for the study of opioid receptors. Pharmacol. Rev. 39 (1987) 197-249
18. Lizasoaín I., Leza J.C., Cuellar B., Moro M.A., and Lorenzo P. Inhibition of morphine withdrawal by lamotrigine: involvement of nitric oxide. Eur. J. Pharmacol. 299 (1996) 41-45
19. Menéndez L., Lastra A., Hidalgo A., Meana A., García E., and Baamonde A. Peripheral opioids act as analgesics in bone cancer pain in mice. NeuroReport 14 (2003) 867-869
20. Morgan J.P. American opiophobia: customary underutilization of opioid analgesics. Adv. Alcohol Subst. Abuse 5 (1985) 163-173
21. Mystakidou K., Katsouda E., Parpa E., Vlahos L., and Tsiatas M.L. Oral transmucosal fentanyl citrate: overview of pharmacological and clinical characteristics. Drug Deliv. 13 (2006) 269-276
22. Pugsley M. The diverse molecular mechanisms responsible for the actions of opioids on the cardiovascular system. Pharmacol. Therapeutics 93 (2002) 51-75
23. Ray S.B., Gupta H., and Gupta Y.K. Up-regulation of m-opioid receptors in the spinal cord of morphine-tolerant rats. J. Biosci. 29 (2004) 51-56
24. Russell N.J., Schaible H.G., and Schmidt R.F. Opiates inhibit the discharges of fine afferent units from inflamed knee joint of the cat. Neurosci. Lett. 76 (1987) 107-112
25. Schaumann W. The paralysing action of morphine on guinea pig ileum. Br. J. Pharmacol. 10 (1955) 456-461
26. Schulz R., and Herz A. Aspects of opiate dependence in the myenteric plexus of the guinea pig. Life Sci. 19 (1976) 1117-1128
27. Stafford K., Gomes A.B., Shen J., and Yoburn B.C. μ-opioid receptor downregulation contributes to opioid tolerance in vivo. Pharmacol. Biochem. Behav. 69 (2001) 233-237
28. Stein C., Millan M.J., Shippenberg T.S., Peter K., and Herz A. Peripheral opioid receptors mediating antinociception in inflammation. Evidence for involvement of mu, delta and kappa receptors. J. Pharmacol. Exp. Ther. 248 (1989) 1269-1275
29. Tamayo A.C., and Díaz Zuluaga P.A. Management of opioid-induced bowel dysfunction in cancer patients. Support. Care Cancer 12 (2004) 613-618
30. Varrassi G., Marinangeli F., Ciccozzi A., Iovinelli G., Facchetti G., and Ciccone A. Intra-articular buprenorphine after knee arthroscopy. A randomised, prospective, double-blind study. Acta Anaesthesiol. Scand. 43 (1999) 51-55
31. Viscusi E.R., Goldstein S., Witkowski T., Andonakakis A., Jan R., Gabriel K., Du W., Techner L., and Wallin B. Alvimopan, a peripherally acting mu-opioid receptor antagonist, compared with placebo in postoperative ileus after major abdominal surgery. Results of a randomized, double-blind, controlled study. Surg. Endosc. 20 (2006) 64-70
32. Wenk H.N., Brederson J.D., and Honda C.N. Morphine directly inhibits nociceptors in inflamed skin. Neurophysiology 95 (2006) 2083-2097
33. Zimmermann M. Ethical guidelines for investigations of experimental pain in conscious animals. Pain 16 (1983) 109-110