Bioavailability, antinociceptive and antiinflammatory properties of BP 2-94, a histamine H 3 receptor agonist prodrug

Journal of Pharmacology and Experimental Therapeutics

Volumn 281, Issue 3, 1997, Pages 1085-1094

  Rouleau, A ^a   Garbarg, M ^a   Ligneau, X ^b   Mantion, C ^b   Lavie, P ^b   Advenier, C ^c   Lecomte, J M ^b   Krause, M ^d   Stark, H ^d   Schunack, W ^d   Schwartz, J C ^a  

^a INSERM   (France)

^b Laboratoire Bioprojet   (France)

^c CENTRE HOSPITALIER DE VERSAILLES   (France)

^d FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 [[N [1 (1H IMIDAZOL 4 YL) 2 PROPYL]IMINO]PHENYLMETHYL]PHENOL; BP 294; CAPSAICIN; HISTAMINE H3 RECEPTOR AGONIST; IMIDAZOLE DERIVATIVE; PHENYLQUINONE; UNCLASSIFIED DRUG; ZYMOSAN;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ANTINOCICEPTION; AREA UNDER THE CURVE; ARTICLE; DOSE RESPONSE; DRUG BIOAVAILABILITY; DRUG MECHANISM; HISTAMINE RELEASE; HYDROLYSIS; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ADULT; ANIMALS; BIOLOGICAL AVAILABILITY; DOSE-RESPONSE RELATIONSHIP, DRUG; HISTAMINE AGONISTS; HUMANS; IMINES; INFLAMMATION; MALE; MICE; NOCICEPTORS; PHENOLS; PRODRUGS; RATS; RATS, WISTAR;

EID: 15644382969     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (76)

1. 3) of histamine receptor. Nature (Lond.) 302: 832-837, 1983.
2. 3 receptors. Nature (Lond.) 327: 117-123, 1987.
3. 3 receptor binding sites in rat brain membranes: Modulation by guanine nucleotides and divalent cations. Eur. J. Pharmacol. 188: 219-227, 1990.
4. 3 receptor in the control of gastric acid secretion in cats. Am. J. Physiol. 260: G631-G635, 1991.
5. BARNES, P. J.: Histamine receptors in the respiratory tract. In The Histamine Receptor, Receptor Biochemistry and Methodology, ed. by J.-C. Schwartz and H. L. Haas, pp. 253-270, Wiley Liss Inc., New York, 1992.
6. 2-receptor antagonists. Agents Actions 8: 359-365, 1978.
7. BARTH, H., CROMBACH, H., SCHUNACK, W. AND LORENZ, W.: Evidence for a less high acceptor substrate specificity of gastric histamine methyltransferase: methylation of imidazole compounds. Biochem. Biophys. Res. Commun. 29: 1399-1408, 1980.
8. BERGMANN, K. J.: Progabide: a new GABA-mimetic agent in clinical use. Clin. Neuropharmacol. 8: 13-26, 1985.
9. 3 receptors and gastrointestinal functions. Dig. Dis. Sci. 40: 2052-2063, 1995.
10. BOWSHER, R. R., VERBURG, K. M. AND HENRY, D. P.: Rat histamine N-methyltransferase. J. Biol. Chem. 258: 12215-12220, 1983.
11. BROWN, D., TOMCHICK, R. AND AXELROD, J.: The distribution and properties of a histamine-methylating enzyme. J. Biol. Chem. 224: 2948-2950, 1959.
12. BUZZI, M. G., CARTER, W. B., SHIMIZU, T., HEATH III H. AND MOSKOWITZ, M. A.: Dihydroergotamine and sumatriptan attenuate levels of CGRP in plasma in rat superior sagittal sinus during electrical stimulation of the trigeminal ganglion. Neuropharmacology 30: 1193-1200, 1991.
13. CHAILLET, P., MARCAIS-COLLADO, H., COSTENTIN, J., YI, C. C., DE LA BAUME, S. AND SCHWARTZ, J.-C.: Inhibition of enkephalin metabolism by, and antinociceptive activity of bestatin, an aminopeptidase inhibitor. Eur. J. Pharmacol. 86: 329-336, 1983.
14. 3-receptor subtypes. Br. J. Pharmacol. 107: 919-923, 1992.
15. 3 receptors are involved in the control of gastric acid secretion in the conscious cat. Naunyn-Schmiedeberg Arch. Pharmacol. 343: 225-227, 1991.
16. 3 receptor modulation in rat lung and spleen. Clin. Sci. 87: 151-163, 1994.
17. DIMITRIADOU, V., ROULEAU, A., DAM TRUNG TUONG, M., NEWLANDS, G. J. F., MILLER, H. R. P., LUFFAU, G., SCHWARTZ, J.-C. AND GARBARG, M.: Functional relationships between sensory nerve fibers and mast cells of dura mater in normal and inflammatory conditions. Neuroscience 77: 829-840, 1997.
18. 2. Prostaglandins 30: 769-789, 1985.
19. EDDY, W. B. AND LEIMBACH, D.: Synthetic analgesics. II. Dithenylbutenyl and dithenylbutylamines. J. Pharmacol. Exp. Ther. 107: 385-393, 1953.
20. FOREMAN, J.-C.: Substance P and calcitonin gene-related peptide: Effects on mast cells and in human skin. Int. Arch. Allergy Appl. Immunol. 82: 366-371, 1987.
21. FUJIBAYASHI, K. AND IIZUKA, Y.: Profiles of the antinociceptive effects of R-84760, a selective κ-opioid receptor agonist, in the formalin test in mice. Jpn. J. Pharmacol. 68: 57-63, 1995.
22. GAMSE, R., HOLZER, P. AND LEMBECK, F.: Decrease of substance P in primary afferent neurones and impairment of neurogenic plasma extravasation by capsaicin. Br. J. Pharmacol. 68: 207-213, 1980.
23. 3-receptor histamine antagonists. J. Med. Chem. 38: 3342-3350, 1995.
24. GARBARG, M., POLLARD, H., QUACH, T. T. AND SCHWARTZ, J.-C.: Methods in brain histamine research. In Methods in Biogenic Amines Research, ed. by S. Parvez, T. Nagatsu, I. Nayatsu and H. Parvez, pp. 623-662, Elsevier Science Publishers, New York, 1983.
25. GARBARG, M., POLLARD, H., TRUNG TUONG, M. D., SCHWARTZ, J.-C. AND GROS, C.: Sensitive radioimmunoassays for histamine and tele-methylhistamine in the brain. J. Neurochem. 53: 1724-1730, 1989a.
26. 3-receptor ligands on various biochemical indices of histaminergic neuron activity in rat brain. Eur. J. Pharmacol. 164: 1-11, 1989b.
27. 3-receptor agonist. J. Pharmacol. Exp. Ther. 263: 304-310, 1992.
28. 3 receptor for therapeutic use, pharmaceutical compositions acting as agonists of the said receptor and preparation process. US Patent 5 342 960 (30.8.1994).
29. HESTERBERG, R., SATTLER, J., LORENZ, W., STAHLKNECHT, C. D., BARTH, H., CROMBACH, M. AND WEBER, D.: Distribution and metabolism of histamine. Histamine content, diamine oxidase activity and histamine methyltransferase activity in human tissues: fact or fictions? Agents Actions 14: 325-334, 1984.
30. 3-selective ligands. Br. J. Pharmacol. 101: 621-624, 1990.
31. HOLZER, P.: Capsaicin: cellular targets, mechanisms of action, and selectivity for thin sensory neurons. Pharmacol. Rev. 43: 144-201, 1991.
32. HOUGH, L. B., KHANDELWAL, J. K. AND MITTAG, T. W.: Alpha-methylhistamine methylation by histamine methyltransferase. Agents Actions 11: 425-428, 1981.
33. 3-receptor agonists. Bioorg. Med. Chem. Lett. 2: 77-78, 1992.
34. HUNTER, W. M. AND GREENWOOD, F. C.: Preparation of iodine-131 labelled human growth hormone of high specific activity. Nature (Lond.) 194: 495-496, 1962.
35. 3 receptors on cholinergic nerves in human airways. Eur. J. Pharmacol. 163: 383-386, 1989a.
36. 3-receptors modulate nonadrenergic noncholinergic neural bronchoconstriction in guinea-pig in vivo. Eur. J. Pharmacol. 174: 49-55, 1989b.
37. 3-receptors inhibit cholinergic neurotransmission in guinea pig airways. Br. J. Pharmacol. 97: 13-15, 1989.
38. 3-receptors inhibit neurogenic microvascular leakage in airways. J. Appl. Physiol. 68: 21-25, 1990.
39. 3-receptor-mediated downregulation of calcitonin-gene-related peptide release from cardiac C-fibers: A regulatory negative feedback loop. Cir. Res. 78: 863-869, 1996.
40. JILEK, J., POMYKACEK, J., FRYCOVA, H. AND POLIVKA, Z.: Synthesis of analogues of progabide and fengabine. Cesk. Farm. 39: 249-253, 1990.
41. KAPLAN, J. P., RAIZON, B. M., DESARMIEN, M., FELTZ, P., HEADLY, P. M., WORMS, P., LLOYD, K. G. AND BARTHOLINI, G.: New anticonvulsants: Shiff bases of γ-aminobutyric acid and γ-aminobutyramide. J. Med. Chem. 23: 702-704, 1980.
42. KAYSER, V. AND GUILBAUD, G.: Peripheral aspects of opioid activity: Studies in animals. In Peripheral neurons in nociception. Physio-pharmacological aspects, ed. by J. M. Besson, G. Guilbaud and H. Ollat, pp. 13-156, John Libbey Eurotext, Paris, 1994.
43. 3 receptor agonists. J. Med. Chem. 38: 4070-4079, 1995.
44. KUROSE, I., POTHOULAKIS, C., LAMONT, J. T., ANDERSON, D. C., PAULSON, J. C., MIYASAKA, M., WOLF, R. AND GRANGER, D. N.: Clostridium difficile toxin A-induced microvascular dysfunction. J. Clin. Invest. 94: 1919-1926, 1994.
45. 3-receptor agonist. J. Med. Chem. 35: 4434-4441, 1992.
46. MAGGI, C. A.: Tachykinins and calcitonin gene-related peptide (CGRP) as co-transmitters released from peripheral endings of sensory nerves. Prog. Neurobiol. 45: 1-45, 1995.
47. MATSUBARA, T., MOSKOWITZ, M. A. AND HUANG, Z.: UK-14,304, R(-)-α-methylhistamine and SMS 201-995 block plasma protein leakage within dura mater by prejunctional mechanisms. Eur. J. Pharmacol. 224: 145-150, 1992.
48. 3 receptors? Digestion 56: 145-152, 1995.
49. MOSKOWITZ, M. A.: The visceral organ brain: Implications for the pathophysiology of vascular head pain. Neurology-41: 182-186, 1991.
50. 3 receptor. Eur. J. Pharmacol. 277: 45-49, 1995.
51. 3-receptor on mast cells in the rat skin. Arch. Int. Pharmacodyn. 328: 307-314, 1994.
52. 3-receptors. Eur. J. Pharmacol. 273: 83-88, 1995.
53. PARKER, R. B. AND WAUD, D. R.: Pharmacological estimation of drug-receptor dissociation constants. Statistical evaluation. I. Agonists J. Pharmacol Exp Ther. 177: 1-24, 1971.
54. PAYAN, D. G.: Neuropeptides and inflammation: the role of substance P. Ann Rev. Med. 40: 341-352, 1989.
55. PRINZ, C., KAJIMURA, M., SCOTT, D. R., MERCIER, F., HELANDER, H. F. AND SACHS, G.: Histamine secretion from rat enterochromaffin like cells. Gastroenterology 105: 449-461, 1993.
56. RAO, T. S., CURRIE, J. L., SHAFFER, A. F. AND ISAKSON P. C.: In vivo characterization of zymosan-induced mouse peritoneal inflammation. J. Pharmacol Exp. Ther. 269: 917-925, 1994.
57. 1 receptor antagonists: non-specific effects of racemic RP67580. Br. J. Pharmacol. 110: 1607-1613, 1993.
58. 3-receptor mediated inhibition of serotonin release in the rat brain cortex. Naunyn Schmiedeberg Arch. Pharmacol. 337: 588-590, 1988.
59. 3 receptors. Naunyn-Schmiedeberg Arch. Pharmacol. 340: 633-638, 1989.
60. 3 receptors. J. Neural Transm. [Gen. sect.] 93: 1-10, 1993.
61. 3 receptor. Agents Actions 30: 13-23, 1990a.
62. SCHWARTZ, J.-C., ARRANG, J.-M., GARBARG, M., GULAT-MARNAY, C. AND POLLARD, H.: Modulation of histamine synthesis and release in brain via presynaptic autoreceptors and heteroreceptors. Presynaptic receptors and the question of autoregulation of neurotransmitter release. Ann. N.Y. Acad. Sci. 604: 40-54, 1990b.
63. SCHWARTZ, J.-C., ARRANG, J.-M., GARBARG, M., POLLARD, H. ANU RUAT, M.: Histaminergic transmission in the mammalian brain. Physiol. Rev. 71: 1-51, 1991.
64. SIEGMUND, E., CADMUS, R. AND LU, G.: A method for evaluating both non-narcotic and narcotic analgesics. Proc. Soc. Exp. Biol. Med. 95: 729-731, 1957.
65. 3-receptor agonist. J. Med. Chem. 38: 1593-1599, 1995.
66. 3 receptors-mediated inhibition of gastric acid secretion in conscious dogs. Naunyn-Schmiedeberg Arch. Pharmacol. 347: 61-65, 1993.
67. 3 receptors in the dog. Scand. J. Gastroenterol. 31: 631-638, 1996.
68. 3-receptor antagonists. Eur. J. Med. Chem. 29: 695-700, 1994.
69. 3-receptor antagonists of the amide type. Eur. J. Pharm. Sci. 3: 95-104, 1995.
70. STEFANOVA, Z., NEYCHEV, H., IVANOSKA, N. AND KOSTOVA, I.: Effect of a total extract from Fraxinus ornus stem bark and esculin on zymosan-and carrageenan-induced paw oedema in mice. J. Ethnopharmacol. 46: 101-106, 1995.
71. STRETTON, D., MIURA, M., BELVISI, M. G. AND BARNES, P. J.: Calcium-activated potassium channels mediate prejunctional inhibition of peripheral sensory nerves. Proc. Natl. Acad. Sci. U.S.A. 89: 1325-1329, 1992.
72. TERNYNCK, T. AND AVRAMEAS, S.: Conjugation of p-benzoquinone treated enzyme with antibodies and Fab fragments. Immunochemistry 14: 767-774, 1977.
73. 3-subtype. J. Pharmacol. Exp. Ther. 243: 874-880, 1987.
74. 3 receptor. Eur. J. Med. Chem. 27: 511-517, 1992.
75. 3-receptor agonist, 4-(1H-imidazol-4-ylmethyl) piperidine. J. Med. Chem. 37: 332-333, 1994.
76. VON VOIGTLANDER, P. F. AND LEWIS, R. A.: Analgesic and mechanistic evaluation of spiradoline, a potent kappa opioid. J. Pharmacol. Exp. Ther. 246: 259-262, 1988.