Second-generation histamine H2-receptor antagonists with gastric mucosal defensive properties

Mini-Reviews in Medicinal Chemistry

Volumn 9, Issue 5, 2009, Pages 581-589

  Ichikawa, Takafumi ^a   Hotta, Kyoko ^a   Ishihara, Kazuhiko ^b  

^a KITASATO UNIVERSITY SCHOOL OF MEDICINE   (Japan)

^b KITASATO UNIVERSITY GRADUATE SCHOOL OF MEDICAL SCIENCES   (Japan)

Author keywords

Calcitonin gene related peptide (CGRP); Capsaicin sensitive nerves; Gastroprotective action; Histamine H2 receptor antagonists; Lafutidine; Mucin; Roxatidine; Structure activity relationship

Indexed keywords

[3 [3 (PIPERIDINOMETHYL)PHENOXY]PROPYL]ACETAMIDE DERIVATIVE; ACETAMIDE DERIVATIVE; ANTACID AGENT; CALCITONIN GENE RELATED PEPTIDE; CIMETIDINE; FAMOTIDINE; HISTAMINE H2 RECEPTOR ANTAGONIST; LAFUTIDINE; MUCIN; NITRIC OXIDE SYNTHASE INHIBITOR; NIZATIDINE; PHENOXYPROPYLACETAMIDE DERIVATIVE; PROTON PUMP INHIBITOR; RANITIDINE; ROXATIDINE; TETRODOTOXIN; UNCLASSIFIED DRUG; HISTAMINE H2 RECEPTOR;

CELL PROTECTION; CLINICAL TRIAL; DRUG ANTAGONISM; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; HUMAN; NONHUMAN; PEPTIC ULCER; REVIEW; STOMACH ACID SECRETION; STOMACH MUCOSA LESION; STOMACH PROTECTION; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMISTRY; DRUG EFFECT; METABOLISM; PHYSIOLOGY; SECRETION; STOMACH ACID; STOMACH MUCOSA;

ANIMALS; GASTRIC ACID; GASTRIC MUCOSA; HISTAMINE H2 ANTAGONISTS; HUMANS; RECEPTORS, HISTAMINE H2; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 67649892035     PISSN: 13895575     EISSN: None     Source Type: Journal    
DOI: 10.2174/138955709788167646     Document Type: Review

References (88)

1. Schwarz, K. Über penetrierende Magen und Jejunalgeschwüre. Beitr. Klin. Chir., 1910, 67, 96-128.
2. Isenberg, J.I.; Spector, H.; Hootkin, L.A.; Pitcher, J.L. An apparent exception to Schwarz's dictum, "no acid - no ulcer". N. Engl. J. Med., 1971, 285, 620.
3. 2-receptors. Nature, 1972, 236, 385-90.
4. 2-receptor antagonist. Br. J. Pharmacol., 1975, 53, 435-6.
5. Buyniski, R.L.; Cavanagh, A.W.; Pircio, A.A.; Crenshaw, R.R., In Highlights in Receptor Chemistry; Melchiorre, C.; Gianella, M., Eds.; Elsevier Science Publishers: Amsterdam, 1984; pp. 195-215.
6. 2 receptors. J. Med. Chem., 1981, 24, 913-20.
7. 2-receptor antagonists? Aliment. Pharmacol. Ther., 1987, 1(Suppl 1), 493S-503S.
8. Kinoshita, M.; Kume, E.; Tamaki, H. J. Pharmacol. Exp. Ther., 1995, 275, 494-501.
9. Kinoshita, M.; Tamaki, H. Roles of prostaglandins, nitric oxide and the capsaicin-sensitive sensory nerves in gastroprotection produced by ecabet sodium. Dig. Dis. Sci., 1997, 42, 83-90.
10. Kishimoto, M.; Yanai, H.; Okazaki, Y.; Matsui, H.; Yoshida, T.; Okita, K. Characteristics of gastric mucus in elderly patients with gastric ulcers. Hepatogastroenterology, 2001, 48, 1594-8.
11. Lam, S.K. Why do ulcers heal with sucralfate? Scand. J. Gastroenterol. Suppl., 1990, 173, 6-16.
12. Marshall, B.J.; Warren, J.R. Unidentified curved bacilli in the stomach of patients with gastritis and peptic ulceration. Lancet, 1984, 1, 1311-5.
13. Peterson, W.L. Helicobacter pylori and peptic ulcer disease. N. Engl. J. Med., 1991, 324, 1043-8.
14. Sato, N.; Kawano, S.; Tsuji, S.; Ogihara, T.; Yamada, S. Gastric blood flow in ulcer diseases. Scand. J. Gastroenterol. Suppl., 1995, 208, 14-20.
15. Tsuji, S.; Kawano, S.; Hayashi, N.; Tsujii, M.; Takei, Y.; Nagano, K.; Sasayama, Y.; Kobayashi, I.; Fusamoto, H.; Kamada, T. Simultaneous analysis of mucosal and submucosal hemodynamics using infrared electronic endoscopy: effects of intraluminal acid on ulcer scars. Endoscopy, 1995, 27, 679-82.
16. Wolfe, M.M.; Lichtenstein, D.R.; Singh, G. Gastrointestinal toxicity of nonsteroidal antiinflammatory drugs. N. Engl. J. Med., 1999, 340, 1888-99.
17. Hagiwara, T.; Mukaisho, K.; Ling, Z. Q.; Sakano, T.; Sugihara, H.; Hattori, T. Rebamipide contributes to reducing adverse effects of long-term administration of omeprazole in rats. Dig. Dis. Sci., 2007, 52, 988-94.
18. Ichikawa, T.; Ito, Y.; Saegusa, Y.; Iwai, T.; Goso, Y.; Ikezawa, T.; Ishihara, K. Effects of combination treatment with famotidine and methylmethionine sulfonium chloride on the mucus barrier of rat gastric mucosa. J. Gastroenterol. Hepatol., 2009, in press.
19. Kinoshita, M.; Noto, T.; Tamaki, H. Effect of a combination of ecabet sodium and cimetidine on experimentally induced gastric lesions and gastric mucosal resistance to ulcerogenic agents in rats. Biol. Pharm. Bull., 1995, 18, 223-6.
20. Murata, H.; Kawano, S.; Tsuji, S.; Kamada, T.; Matsuzawa, Y.; Katsu, K.; Inoue, K.; Kobayashi, K.; Mitsufuji, S.; Bamba, T.; Kawasaki, H.; Kajiyama, G.; Umegaki, E.; Inoue, M.; Saito, I. Combination therapy of ecabet sodium and cimetidine compared with cimetidine alone for gastric ulcer: prospective randomized multicenter study. J. Gastroenterol. Hepatol., 2003, 18, 1029-33.
21. Murata, H.; Kawano, S.; Tsuji, S.; Tsujii, M.; Hori, M.; Kamada, T.; Matsuzawa, Y.; Katsu, K.; Inoue, K.; Kobayashi, K.; Mitsufuji, S.; Bamba, T.; Kawasaki, H.; Kajiyama, G.; Umegaki, E.; Inoue, M.; Saito, I. Combination of enprostil and cimetidine is more effective than cimetidine alone in treating gastric ulcer: prospective multicenter randomized controlled trial. Hepatogastroenterology, 2005, 52, 1925-9.
22. Terano, A.; Arakawa, T.; Sugiyama, T.; Yoshikawa, T.; Haruma, K.; Asaka, M.; Shimosegawa, T.; Sakaki, N.; Ishii, H.; Sakamoto, C.; Takahashi, S.; Kinoshita, Y.; Fujioka, T.; Kobayashi, K. A pilot study to evaluate a new combination therapy for gastric ulcer: Helicobacter pylori eradication therapy followed by gastroprotective treatment with rebamipide. J. Gastroenterol. Hepatol., 2006, 21, 103-9.
23. 2-receptor antagonist, on the recurrence of gastric ulcer after healing by drug treatment in rats. Pharmacology, 2000, 61, 83-90.
24. Fukushima, K.; Aoi, Y.; Kato, S.; Takeuchi, K. Gastro-protective action of lafutidine mediated by capsaicin-sensitive afferent neurons without interaction with TRPV1 and involvement of endogenous prostaglandins. World J. Gastroenterol., 2006, 12, 3031-7.
25. 2-receptor antagonist, through enhancement of sensory neuron activation contributes to the reduction of stress-induced gastric mucosal injury in rats. Dig. Dis. Sci., 2007, 52, 469-77.
26. Ichikawa, T.; Ishihara, K.; Saigenji, K.; Hotta, K. Effects of acid-inhibitory antiulcer drugs on mucin biosynthesis in the rat stomach. Eur. J. Pharmacol., 1994, 251, 107-11.
27. Ichikawa, T.; Ishihara, K.; Saigenji, K.; Hotta, K. Structural requirements for roxatidine in the stimulant effect of rat gastric mucin synthesis and the participation of nitric oxide in this mechanism. Br. J. Pharmacol., 1997, 122, 1230-6.
28. Ichikawa, T.; Ishihara, K.; Shibata, M.; Yamaura, T.; Saigenji, K.; Hotta, K. Stimulation of mucin biosynthesis in rat gastric mucosa by FRG-8813 and its structural analogs. Eur. J. Pharmacol., 1996, 297, 87-92.
29. 2-receptor antagonist, lafutidine, on the mucus barrier of human gastric mucosa. J. Gastroenterol. Hepatol., 2007, 22, 1800-5.
30. Marazova, K.; Klouchek, E.; Popov, A.; Ivanov, C.; Krushkov, I.; Ichikawa, T.; Ishihara, K.; Hotta, K. Effect of roxatidine bismuth citrate (MX1) against acetylsalicylic acid- and indomethacin-induced gastric mucosal damage in rats. Methods Find. Exp. Clin. Pharmacol., 1998, 20, 667-72.
31. 3-secretion in rats: relation to capsaicin-sensitive afferent neurons. Dig. Dis. Sci., 2002, 47, 2696-703.
32. 2 receptor antagonist, mediated by capsaicin-sensitive afferent neurons. Dig. Dis. Sci., 2009, 54, 36-45.
33. 2-receptor antagonist, Z-300, on gastric secretion and gastroduodenal lesions in rats: comparison with roxatidine. Jpn. J. Pharmacol., 1992, 59, 275-89.
34. 2-receptor antagonist, in rats. Jpn. J. Pharmacol., 1995, 68, 161-73.
35. Saegusa, Y.; Ichikawa, T.; Iwai, T.; Goso, Y.; Ikezawa, T.; Nakano, M.; Shikama, N.; Saigenji, K.; Ishihara, K. Effects of acid antisecretory drugs on mucus barrier of the rat against 5-fluorouracil-induced gastrointestinal mucositis. Scand. J. Gastroenterol., 2008, 43, 531-7.
36. 2-receptor antagonist, increases serum calcitonin generelated peptide in rats after water immersion-restraint stress. J. Lab. Clin. Med., 2003, 141, 102-5.
37. 2) receptor antagonist with gastroprotective activity. I. Synthesis and pharmacological evaluation of N-phenoxypropylacetamide derivatives with thioether function. Chem. Pharm. Bull. (Tokyo), 1998, 46, 610-5.
38. 2 receptor antagonist, in rats and dogs. Eur. J. Pharmacol., 1993, 235, 245-53.
39. Shiratsuchi, K.; Fuse, H.; Hagiwara, M.; Mikami, T.; Miyasaka, K.; Sakuma, H. Cytoprotective action of roxatidine acetate HCl. Arch. Int. Pharmacodyn. Ther., 1988, 294, 295-304.
40. Sugiyama, T.; Hatanaka, Y.; Iwatani, Y.; Jin, X.; Kawasaki, H. Lafutidine facilitates calcitonin gene-related peptide (CGRP) nerve-mediated vasodilation via vanilloid-1 receptors in rat mesenteric resistance arteries. J. Pharmacol. Sci., 2008, 106, 505-11.
41. 2 receptor antagonist, roxatidine, stimulates mucus secretion and synthesis by cultured rabbit gastric mucosal cells. J. Physiol. Pharmacol., 1995, 46, 503-11.
42. 2-receptor antagonists: an overview. J. Int. Med. Res., 1989, 17(Suppl 1), 9A-16A.
43. Ganellin, C. R. In Molecular and Quantum Pharmacology, Bergmann, E.; Pullman, B., Eds.; Kluwer Academic Publishers: Dordrecht, 1974; pp. 45-53.
44. 2-receptor antagonists: an overview. Scand. J. Gastroenterol. Suppl., 1981, 69, 1-9.
45. 2-receptor antagonists. Relationship between intrinsic potency and effective plasma concentrations. Clin. Pharmacokinet., 1991, 20, 218-36.
46. Campoli-Richards, D.M.; Clissold, S.P. Famotidine. Pharmacodynamic and pharmacokinetic properties and a preliminary review of its therapeutic use in peptic ulcer disease and Zollinger-Ellison syndrome. Drugs, 1986, 32, 197-221.
47. 2-receptor antagonists on the mouse isolated stomach assay. Br. J. Pharmacol., 1985, 86, 581-7.
48. Ganellin, C.R., In Frontiers in Histamine Research, Ganellin, C.R., Ed.; Pergamon Press: Oxford, 1985; pp. 47-59.
49. 3H-cimetidine binding and histamine-stimulation of cellular cAMP in isolated guinea pig gastric glands. Jpn. J. Pharmacol., 1987, 45, 97-105.
50. 2-receptor antagonistic property of FRG-8813, a novel anti-ulcer drug. Nippon Yakurigaku Zasshi, 1995, 105, 231-41.
51. Chaudhury, T.K.; Jacobson, E.D. Prostaglandin cytoprotection of gastric mucosa. Gastroenterology, 1978, 74, 58-63.
52. Robert, A. Cytoprotection by prostaglandins. Gastroenterology, 1979, 77, 761-7.
53. Szabo, S.; Trier, J.S.; Frankel, P.W. Sulfhydryl compounds may mediate gastric cytoprotection. Science, 1981, 214, 200-2.
54. Tarnawski, A.; Hollander, D.; Gergely, H.; Stachura, J. Comparison of antacid, sucralfate, cimetidine, and ranitidine in protection of the gastric mucosa against ethanol injury. Am. J. Med., 1985, 79, 19-23.
55. Rees, W.D.W.; Brown, C.M., In Bockus Gastroenterology, 5th edn, Haubrich, W.S.; Schaffner, F.; Berk, J.E., Eds.; Saunders Company: Philadelphia, 1995; pp. 582-614.
56. Allen, A.; Hutton, D.A.; Leonard, A.J.; Pearson, J.P.; Sellers, L.A. The role of mucus in the protection of the gastroduodenal mucosa. Scand. J. Gastroenterol. Suppl., 1986, 125, 71-8.
57. 2) receptor antagonist with gastroprotective activity. II. Synthesis and pharmacological evaluation of 2-furfuryl-thio and 2-furfurylsulfinyl acetamide derivatives with heteroaromatic rings. Chem. Pharm. Bull. (Tokyo), 1998, 46, 616-22.
58. 2 receptor stably expressed in Chinese hamster ovary cells. Br. J. Pharmacol., 1994, 112, 847-54.
59. 125I]iodinated probes. Proc. Natl. Acad. Sci. USA, 1990, 87, 1658-62.
60. Nishihara, K.; Nozawa, Y.; Nakano, M.; Ajioka, H.; Matsuura, N. Sensitizing effects of lafutidine on CGRP-containing afferent nerves in the rat stomach. Br. J. Pharmacol., 2002, 135, 1487-94.
61. Holzer, P. Neural emergency system in the stomach. Gastroenterology, 1998, 114, 823-39.
62. Sobue, M.; Joh, T.; Oshima, T.; Suzuki, H.; Seno, K.; Kasugai, K.; Nomura, T.; Ohara, H.; Yokoyama, Y.; Itoh, M. Contribution of capsaicin-sensitive afferent nerves to rapid recovery from ethanol-induced gastric epithelial damage in rats. J. Gastroenterol. Hepatol., 2003, 18, 1188-95.
63. Holzer, P. Capsaicin: cellular targets, mechanisms of action, and selectivity for thin sensory neurons. Pharmacol. Rev., 1991, 43, 143-201.
64. Green, T.; Dockray, G.J. Characterization of the peptidergic afferent innervation of the stomach in the rat, mouse and guinea-pig. Neuroscience, 1988, 25, 181-93.
65. Sternini, C.; Reeve, J.R.Jr; Brecha, N. Distribution and characterization of calcitonin gene-related peptide immunoreactivity in the digestive system of normal and capsaicin-treated rats. Gastroenterology, 1987, 93, 852-62.
66. Green, T.; Dockray, G.J. Calcitonin gene-related peptide and substance P in afferents to the upper gastrointestinal tract in the rat. Neurosci. Lett., 1987, 76, 151-6.
67. 2 regulates the neural emergency system through release of calcitonin gene related peptide. Gut, 2003, 52, 1242-9.
68. 2 is attributable to sensitization of CRGP-containing sensory nerves. Gastroenterology, 2001, 120, 134-43.
69. Hayashi, H.; Ohno, T.; Nishiyama, K.; Boku, K.; Katori, M.; Majima, M. Transient prevention of ethanol-induced gastric lesion by capsaicin due to release of endogenous calcitonin gene-related peptide in rats. Jpn. J. Pharmacol., 2001, 86, 351-4.
70. Ichikawa, T.; Ishihara, K.; Kusakabe, T.; Hiruma, H.; Kawakami, T.; Hotta, K. CGRP modulates mucin synthesis in surface mucus cells of rat gastric oxyntic mucosa. Am. J. Physiol., 2000, 279, G82-9.
71. Mizuguchi, S.; Ohno, T.; Hattori, Y.; Kamata, K.; Arai, K.; Saeki, T.; Saigenji, K.; Hayashi, I.; Kuribayashi, Y.; Majima, M. Calcitonin gene-related peptide released by capsaicin suppresses myoelectrical activity of gastric smooth muscle. J. Gastroenterol. Hepatol., 2005, 20, 611-8.
72. Ohno, T.; Hattori, Y.; Komine, R.; Ae, T.; Mizuguchi, S.; Arai, K.; Saeki, T.; Suzuki, T.; Hosono, K.; Hayashi, I.; Oh-Hashi, Y.; Kurihara, Y.; Kurihara, H.; Amagase, K.; Okabe, S.; Saigenji, K.; Majima, M. Roles of calcitonin gene-related peptide in maintenance of gastric mucosal integrity and in enhancement of ulcer healing and angiogenesis. Gastroenterology, 2008, 134, 215-25.
73. 2 in rats. Am. J. Physiol., 2004, 286, G68-75.
74. Onodera, S.; Tanaka, M.; Aoyama, M.; Arai, Y.; Inaba, N.; Suzuki, T.; Nishizawa, A.; Shibata, M.; Sekine, Y. Antiulcer effect of lafutidine on indomethacin-induced gastric antral ulcers in refed rats. Jpn. J. Pharmacol., 1999, 80, 229-35.
75. Ikawa, K.; Shimatani, T.; Azuma, Y.; Inoue, M.; Morikawa, N. Calcitonin gene-related peptide and somatostatin releases correlated with the area under the lafutidine concentration-time curve in human plasma. J. Clin. Pharm. Ther., 2006, 31, 351-6.
76. Shimatani, T.; Inoue, M.; Kuroiwa, T.; Xu, J.; Nakamura, M.; Tazuma, S.; Ikawa, K.; Morikawa, N. Lafutidine, a newly developed antiulcer drug, elevates postprandial intragastric pH and increases plasma calcitonin gene-related peptide and somatostatin concentrations in humans: comparisons with famotidine. Dig. Dis. Sci., 2006, 51, 114-20.
77. Ichikawa, T.; Ishihara, K.; Saigenji, K.; Hotta, K. Lafutidine-induced stimulation of mucin biosynthesis mediated by nitric oxide is limited to the surface mucous cells of rat gastric oxyntic mucosa. Life Sci., 1998, 62, PL259-64.
78. Ichikawa, T.; Ishihara, K.; Kusakabe, T.; Kawakami, T.; Hotta, K. Stimulant effect of nitric oxide generator and roxatidine on mucin biosynthesis of rat gastric oxyntic mucosa. Life Sci., 1999, 65, PL41-6.
79. Kato, S.; Tanaka, A.; Kunikata, T.; Umeda, M.; Takeuchi, K. Protective effect of lafutidine against indomethacin-induced intestinal ulceration in rats: relation to capsaicin-sensitive sensory neurons. Digestion, 2000, 61, 39-46.
80. 2-receptor antagonist: mucosal protection throughout gastrointestinal tract mediated by capsaicin-sensitive afferent neurons. Curr. Pharm. Des., 2004, 1, 133-44.
81. Onodera, S.; Shibata, M.; Tanaka, M.; Inaba, N.; Arai, Y.; Aoyama, M.; Lee, B.; Yamaura, T. Antiulcer effect of lafutidine on indomethacin-induced gastric antral ulcers in refed rats. Arzneimittelforschung, 1999, 49, 519-26.
82. 2-receptor antagonist, on reflux esophagitis in rats through capsaicin-sensitive afferent neurons. J. Pharmacol. Sci., 2003, 93, 55-61.
83. Ichikawa, T.; Ishihara, K.; Kusakabe, T.; Kurihara, M.; Kawakami, T.; Takenaka, T.; Saigenji, K.; Hotta, K. Distinct effects of tetragastrin, histamine, and CCh on rat gastric mucin synthesis and contribution of NO. Am. J. Physiol., 1998, 274, G138-46.
84. 2-receptor antagonist, on dextran sulfate sodium-induced colonic inflammation through capsaicin-sensitive afferent neurons in rats. Dig. Dis. Sci., 2004, 49, 1696-704.
85. Someya, A.; Horie, S.; Yamamoto, H.; Murayama, T. Modifications of capsaicin-sensitive neurons in isolated guinea pig ileum by [6]-gingerol and lafutidine. J. Pharmacol. Sci., 2003, 92, 359-66.
86. 2-receptor antagonist, against indomethacin-induced damage in rats - role of endogenous nitric oxide. Med. Sci. Monit., 2001, 7, 869-77.
87. Asahina, A.; Moro, O.; Hosoi, J.; Lerner, E.A.; Xu, S.; Takashima, A.; Granstein, R.D. Specific induction of cAMP in Langerhans cells by calcitonin gene-related peptide: relevance to functional effects. Proc. Natl. Acad. Sci. U S A, 1995, 92, 8323-7.
88. Beresford, L.; Orange, O.; Bell, E.B.; Miyan, J.A. Nerve fibres are required to evoke a contact sensitivity response in mice. Immunology, 2004, 111, 118-25.