Novel qualitative structure-activity relationships for the antinociceptive actions of H2 antagonists, H3 antagonists and derivatives

Journal of Pharmacology and Experimental Therapeutics

Volumn 283, Issue 3, 1997, Pages 1534-1543

  Hough, L B ^a   Nalwalk, J W ^a   Li, B Y ^a   Leurs, R ^b   Menge, W M P B ^b   Timmerman, H ^b   Carlile, M E ^a   Cioffi, C ^c   Wentland, M ^c  

^a ALBANY MEDICAL COLLEGE   (United States)

^b VU UNIVERSITY AMSTERDAM   (Netherlands)

^c Research Rensselaer Polytechnic Institute   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 [3 (3 ANILINOPROPOXY)BENZYL]PIPERIDINE; 1 CYANO 2 [2 [(4 IMIDAZOLYL)METHYL]ETHYL] 3 METHYLGUANIDINE; ANALGESIC AGENT; ANTIHISTAMINIC AGENT; BURIMAMIDE; CIMETIDINE; CLOBENPROPIT; HISTAMINE H2 RECEPTOR ANTAGONIST; HISTAMINE H3 RECEPTOR ANTAGONIST; IMPROGAN; METIAMIDE; NORBURIMAMIDE; RANITIDINE; THIOPERAMIDE; TIOTIDINE; UNCLASSIFIED DRUG; VUF 4684; VUF 4685; VUF 4686; VUF 4687; VUF 4740; VUF 4741; VUF 5261; VUF 5262; VUF 8298; VUF 8299; ZOLANTIDINE;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANTINOCICEPTION; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG POTENCY; HOT PLATE TEST; INTRACEREBROVENTRICULAR DRUG ADMINISTRATION; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION; TAIL FLICK TEST;

ANALGESICS, NON-NARCOTIC; ANIMALS; BURIMAMIDE; DOSE-RESPONSE RELATIONSHIP, DRUG; HISTAMINE ANTAGONISTS; HISTAMINE H2 ANTAGONISTS; IMIDAZOLES; MALE; PIPERIDINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, HISTAMINE H3; STRUCTURE-ACTIVITY RELATIONSHIP; THIOUREA;

EID: 0031459938     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (72)

1. 2 biosynthesis in human platelets by burimamide. Br. J. Pharmacol. 71: 157-164, 1980.
2. APPELBAUM, B. D. AND HOLTZMAN, S. G.: Stress-induced changes in the analgesic and thermic effects of morphine induced centrally. Brain Res. 358: 303-308, 1985.
3. ARRANG, J.-M., GARBARG, M., LANCELOT, J.-, LECOMTE, J.-M., ROBBA, M.-F. AND SCHWARTZ, J.-C.: (4-Imidazolyl)piperidines, the preparation thereof and their application in therapy. U. S. Patent 4,707487, 1987.
4. BARKE, K. E. AND HOUGH, L. B.: Characterization of basal and morphine-induced histamine release in the rat periaqueductal gray. J. Neurochem. 63: 238-244, 1994.
5. 1- and muscarinic receptor antagonist activity of cimetidine and tiotidine in the guinea pig isolated ileum. Agents Actions 11: 699-705, 1981.
6. 2-receptor antagonists on gastric histamine methyl-transferaae. Agents Actions 3: 138-147, 1973.
7. BHATTACHARYA, S. K. AND PARMAR, S. S.: Antinociceptive effect of intracerebroventricularly administered histamine in rats. Res. Commun. Chem. Pathol. Pharmacol. 49: 125-136, 1985.
8. BIEGANSKI, T., KUSCHE, J., FEUSSNER, K. D., HESTERBERG, R., RICHTER, H. AND LORENZ, W.: Human intestinal diamine oxidase: Substrate specificity and comparative inhibitor study. Agents Actions 10: 108-110, 1980.
9. 2-receptors. Nature 236: 385-390, 1972.
10. 2-receptor antagonists. Fed. Proc. 35: 1931-1934, 1976.
11. 2-receptor antagonists. In Pharmacological and Biochemical Properties of Drug Substances, ed. by M. E. Goldberg, pp. 329-353, American Pharmaceutical Association, Washington, D.C., 1977.
12. 2-receptor antagonist, with those of cimetidine, ranitidine and Tiotidine. J. Pharmacol. Exp. Ther. 224: 171-179, 1983.
13. COOPER, D. G., YOUNG, R. C., DURANT, G. J. AND GANELLIN, C. R.: Histamine receptors. Comp. Med. Chem. 3: 323-421, 1990.
14. CRANE, L. A. AND GLICK, S. D.: Simple cannula for repeated intracerebral drug administration in rats. Pharmacol. Biochem. Behav. 10: 799-800, 1979.
15. D'AMOUR, F. E. AND SMITH, D. L.: A method for determining loss of pain sensation. J. Pharmacol. Exp. Ther. 72: 74-79, 1941.
16. DEWS, P. B. AND GRAHAM, J. D. P.: The antihistamine substance 2786 r.p. Br. J. Pharmacol. 1: 278-286, 1946.
17. EDDY, N. B. AND LEIMBACH, D.: Synthetic analgesics, II Dithienylbutenyl and dithienylbutylamines. J. Pharmacol. Exp. Ther. 107: 385-393, 1953.
18. 2-adrenoceptors in the ventrolateral medulla. Eur. J. Pharmacol. 134: 1-13, 1987.
19. 1-Imidazoline receptors: Definition, characterization, distribution and transmembrane signaling. In The Imidazoline Receptor: Pharmacology, Functions, Ligands, and Relevance to Biology and Medicine, ed. by D. J. Reis, P. Bousquet and A. Parini, pp. 22-42, N.Y. Academy of Science, New York, 1995.
20. 1-imidazoline receptors. J. Cardiovasc. Pharmacol. 20: suppl. 4, S1-S10, 1992.
21. FUJISAWA PHARMACEUTICAL CO. LTD.: Jpn. Kokai Tokkyo Koh Patent 58 90,569, 1983.
22. GANELLIN, C. R.: Chemistry and structure-activity relationships of drugs acting at histamine receptors. In Pharmacology of Histamine Receptors, ed. by C. R. Ganellin and M. E. Parsons, pp. 10-102, John Wright & Sons, Ltd., Bristol, 1982.
23. GLICK, S. D. AND CRANE, L. A.: Opiate-like and abstinence-like effects of intracerebral histamine administration in rats. Nature 273: 547-549, 1978.
24. 2 receptors in opioid antinociception. J. Pharmacol. Exp. Ther. 250: 476-484, 1989.
25. 2 antagonists. J. Pharmacol. Exp. Ther. 248: 262-267, 1989.
26. HILL, S. J.: Distribution, properties, and functional characteristics of three classes of histamine receptor. Pharmacol. Rev. 42: 45-83, 1990.
27. 2 receptors in the periaqueductal grey. Brain Res. 588: 58-66, 1992.
28. IDÄNPÄÄN-HEIKKILÄ, J. J., KALSO, E. A. AND SEPPÄLÄ, T.: Antinociceptive actions of dexmedetomidine and the kappa-opioid agonist U-50,488H against noxious thermal, mechanical and inflammatory stimuli. J. Pharmacol. Exp. Ther. 271: 1306-1313, 1994.
29. ITOH, Y., OISHI, R., NISHIBORI, M. AND SAEKI, K.: Characterization of histamine release from the hypothalamus as measured by in vivo microdialysis. J. Neurochem. 56: 769-774, 1991.
30. KARPPANEN, H.: Interrelationships between clonidine and histaminergic mechanisms. Trends Pharmacol Sci. 18: 35-37, 1981.
31. 2-receptor antagonists with GABA and benzodiazepine binding sites in the CNS. Eur. J. Pharmacol. 88: 241-245, 1983.
32. LAMBERTI, C., BARTOLINI, A., GHELARDINI, C. AND MALMBERG-AIELLO, P.: Investigation into the role of histamine receptors in rodent antinociception. Pharmacol. Biochem. Behav. 53: 567-574, 1996.
33. LAUNAY, J.-M., BONDOUX, D., OSET-GASQUE, M.-J., EMAMI, S., MUTEL, V., HAIMART, M. AND GESPACH, C.: Increase of human platelet serotonin uptake by atypical histamine receptors. Am. J. Physiol. Regul. Integr. Comp. Physiol. 266: R526-R536, 1994.
34. 3 receptor revealed. Br. J. Pharmacol. 116: 2315-2321, 1995a.
35. 3 receptor. In Progress in Drug Research, ed. by E. Jucker, pp. 107-165, Birkhauser Verlag, Basel, Switzerland, 1995b.
36. 3 receptor assays. Evidence for H3 receptor heterogeneity? J. Pharmacol. Exp. Ther. 276: 1009-1015, 1996.
37. 3 receptor: A target for developing new drugs. Prog. Drug Res. 39: 127-165, 1992.
38. 2-histamine receptor blockers and opiate analgesia in mice. Methods Find. Exp. Clin. Pharmacol. 12: 671-678, 1990.
39. LI, B. Y., NALWALK, J. W., BARKER, L. A., CUMMING, P., PARSONS, M. E. AND HOUGH, L. B.: Characterization of the antinociceptive properties of cimetidine and a structural analog. J. Pharmacol. Exp. Ther. 276: 500-508, 1996.
40. LI, B. Y., NALWALK, J. W., FINKEL, J. M., GLICK, S. D. AND HOUGH, L. B.: SKF92374, a cimetidine analog, produces mechanical and thermal antinociception in the absence of motor impairment. Analgesia 3: 15-20, 1997a.
41. LI, B. Y., NALWALK, J. W. AND HOUGH, L. B.: Effects of naltrexone and histamine antagonists on the antinociceptive activity of the cimetidine analog SKF92374 in rats. Brain Res. 748: 168-174, 1997b.
42. MALMBERG-AIELLO, P., LAMBERTI, C., GHELARDINI, C., GIOTTI, A. AND BARTOLINI, A.: Role of histamine in rodent antinociception. Br. J. Pharmacol. 111: 1269-1279, 1994.
43. 2-receptor blocking drugs burimamide and cimetidine on noradrenergic transmission in the isolated aorta of the rabbit and atria of the guinea-pig. Br. J. Pharmacol. 67: 535-543, 1979.
44. MOCHIZUKI, T., YAMATODANI, A., OKAKURA, K., TAKEMURA, M., INAGAKI, N. AND WADA, H.: In vivo release of neuronal histamine in the hypothalamus of rats measured by microdialysis. Naunyn-Schmiedebergs Arch. Pharmacol. 343: 190-195, 1991.
45. NETTI, C., BOSSA, R., GALATULAS, I., SIBILIA, V. AND PECILE, A.: Antinociceptive effect of centrally administered cimetidine and dimaprit in the rat. Pharmacology 28: 262-267, 1984.
46. 2-receptor agonists and antagonists on nociception in the rat. Agents Actions 23: 247-249, 1988.
47. 2-receptor antagonists with the noradrenergic system in rat brain. Eur. J. Pharmacol. 51: 71-75, 1978.
48. 2-receptor blocking drugs with the noradrenergic system in rat brain and heart. Eur. J. Pharmacol. 68: 69-72, 1980.
49. OLUYOMI, A. O. AND HART, S. L.: Involvement of histamine in naloxone-resistant and naloxone-sensitive models of swim stress-induced antinociception in the mouse. Neuropharmacology 30: 1021-1027, 1991.
50. ONODERA, K. AND OGURA, Y.: Opiate-like actions by intracerebroventricular histamine in mice and its antagonism by naloxone. Jpn. J. Oral Biol. 25: 1144-1147, 1983.
51. PAROLARO, D., PATRINI, G., MASSI, P., MAINARDI, P., GIAGNONI, G., SALA, M. AND GORI, E.: Histamine as a central modulator of rat intestinal transit. J. Pharmacol. Exp. Ther. 249: 324-328, 1989.
52. PAXINOS, G. AND WATSON, C.: The Rat Brain in Stereotaxic Coordinates, Academic Press, Sydney, 1988.
53. RAIBLE, D. G., LENAHAN, T., FAYVILEVICH, Y., KOSINSKI, R. AND SCHULMAN, E. S.: Pharmacologic characterization of a novel histamine receptor on human eosinophils. Am. J. Respir. Crit. Care Med. 149: 1506-1511, 1997.
54. SAXENA, S. P., BRANDES, L. J., BECKER, A. B., SIMONS, K. J., LABELLA, F. S. AND GERRARD, J. M.: Histamine is an intracellular messenger mediating platelet aggregation. Science 243: 1596-1599, 1989.
55. 2 receptor antagonists on androgen action in vivo and dihydrotestosterone binding to the rat prostate androgen receptor in vitro. Biochem. Pharmacol. 31: 677-684, 1982.
56. 3H]cimetidine to rat brain tissue. Agents Actions 10: 422-426, 1980.
57. SMYTHE, J. W. AND PAPPAS, B. A.: Noradrenergic and serotonergic mediation of the locomotor and antinociceptive effects of clonidine in infant and adult rats. Pharmacol. Biochem. Behav. 34: 413-418, 1989.
58. 2 antihistamines. J. Lab Clin Med. 97: 112-122, 1981.
59. STERK, G. J., VAN DER GOOT, H. AND TIMMERMAN, H.: Studies on histaminergic compounds VI. Synthesis and structure-activity relationships of a series of cimetidine and impromidine congeners. Eur. J. Med. Chem. 22: 427-432, 1987.
60. TAKAYANAGI, I., IWAYAMA, Y. AND KASUYA, Y.: Narcotic antagonistic action of cimetidine on the guinea-pig ileum. J. Pharm. Pharmacol. 30: 519-520, 1978.
61. TASKER, R. A. R. AND MELZACK, R.: Different alpha-receptor subtypes are involved in clonidine-produced analgesia in different pain tests. Life Sci. 44: 9-17, 1989.
62. TAYLOR, K. M.: Comparison of the antihistaminic effect of burimamide and mepyramine and their effect on the activity of histamine methyltransferase. Biochem. Pharmacol. 22: 2775-2776, 1973.
63. 3 receptor antagonist; in vitro and in vivo studies. J. Pharmacol. Exp. Ther. 275: 598-604, 1995.
64. THOBURN, K. K., HOUGH, L. B., NALWALK, J. W. AND MISCHLER, S. A.: Histamine-induced modulation of nociceptive responses. Pain 58: 29-37, 1994.
65. THOMAS, B. AND PRELL, G. D.: Imidazoleacetic acid, γ-aminobutyric acid receptor agonist, can be formed in rat brain by oxidation of histamine. J. Neurochem. 65: 818-826, 1995.
66. 2 antagonists not caused by gaba blockade. Eur. J. Pharmacol. 124: 231-241, 1986.
67. 3-receptor. Eur. J. Med. Chem. 27: 511-517, 1992.
68. 3 ligands. Methods Find. Exp. Clin. Pharmacol. 14: 747-751, 1992.
69. 3 receptor antagonists: the effect of chain length variation of the alkyl spacer and modifications of the n-thiourea substituent. J. Med. Chem. 38: 2244-2250, 1995.
70. 3-histamine receptor subtypes. Mol. Pharmacol. 38: 610-613, 1990.
71. YEUNG, J. C. AND RUDY, T. A.: Multiplicative interaction between narcotic agonisms expressed at spinal and supraspinal sites of antinociceptive action as revealed by concurrent intrathecal and intracerebroventricular injections of morphine. J. Pharmacol. Exp. Ther. 215: 633-642, 1980.
72. 2 receptor histamine antagonists. J. Med. Chem. 31: 656-671, 1988.