Molecular mechanisms of 5-HT3 and NK1 receptor antagonists in prevention of emesis

European Journal of Pharmacology

Volumn 722, Issue 1, 2014, Pages 26-37

  Rojas, Camilo ^a   Raje, Mithun ^a   Tsukamoto, Takashi ^a   Slusher, Barbara S ^a  

^a JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

5 HT3 receptor; Aprepitant; Dolasetron; Granisetron; Netupitant; NK1 receptor; Ondansetron; Palonosetron; Tropisetron

Indexed keywords

2 [3,5 BIS(TRIFLUOROMETHYL)BENZYLOXY] 4 (3 OXO 1,2,4 TRIAZOL 5 YLMETHYL) 3 PHENYLMORPHOLINE; 2 BENZHYDRYL 3 (2 METHOXYBENZYLAMINO) 1 AZABICYCLO[2.2.2]OCTANE; 3 (2 METHOXYBENZYLAMINO) 2 PHENYLPIPERIDINE; 3 [3,5 BIS(TRIFLUOROMETHYL)BENZYLOXY] 2 PHENYLPIPERIDINE; APREPITANT; BEMESETRON; CASOPITANT; DOLASETRON MESILATE; FOSAPREPITANT; GRANISETRON; METOCLOPRAMIDE; NETUPITANT; NEUROKININ 1 RECEPTOR; NEUROKININ 1 RECEPTOR ANTAGONIST; ONDANSETRON; PALONOSETRON; PROCAINAMIDE; SEROTONIN; SEROTONIN 3 ANTAGONIST; SEROTONIN 3 RECEPTOR; SUBSTANCE P; TROPISETRON; VESTIPITANT;

ALLOSTERISM; ANTIEMETIC ACTIVITY; CHEMOTHERAPY INDUCED NAUSEA AND VOMITING; DRUG EFFICACY; DRUG MECHANISM; DRUG RECEPTOR BINDING; DRUG STRUCTURE; HUMAN; INTERNALIZATION; PRIORITY JOURNAL; REVIEW; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION;

5-HT(3) RECEPTOR; APREPITANT; DOLASETRON; GRANISETRON; NETUPITANT; NK(1) RECEPTOR; ONDANSETRON; PALONOSETRON; TROPISETRON;

ANIMALS; DRUG DISCOVERY; HUMANS; NEUROKININ-1 RECEPTOR ANTAGONISTS; RECEPTORS, NEUROKININ-1; RECEPTORS, SEROTONIN, 5-HT3; SEROTONIN 5-HT3 RECEPTOR ANTAGONISTS; VOMITING;

EID: 84892868999     PISSN: 00142999     EISSN: 18790712     Source Type: Journal    
DOI: 10.1016/j.ejphar.2013.08.049     Document Type: Review

References (106)

1. M. Aapro Serotonin receptor antagonists P.J. Hesketh, Management of Nausea and Vomiting in Cancer and Cancer Treatment 2005 Jones and Bartlett Publishers, Inc. London 161 180
2. M.S. Aapro, S.M. Grunberg, G.M. Manikhas, G. Olivares, T. Suarez, S.A. Tjulandin, L.F. Bertoli, F. Yunus, B. Morrica, F. Lordick, and A. Macciocchi A phase III, double-blind, randomized trial of palonosetron compared with ondansetron in preventing chemotherapy-induced nausea and vomiting following highly emetogenic chemotherapy Ann. Oncol. 17 2006 1441 1449 (Pubitemid 44400384)
3. E. Basch, A.A. Prestrud, P.J. Hesketh, M.G. Kris, P.C. Feyer, M.R. Somerfield, M. Chesney, R.A. Clark-Snow, A.M. Flaherty, B. Freundlich, G. Morrow, K.V. Rao, R.N. Schwartz, and G.H. Lyman Antiemetics: American society of clinical oncology clinical practice guideline update J. Clin. Oncol. 29 2011 4189 4198
4. M. Bigaud, J. Elands, P.R. Kastner, R.A. Bohnke, L.W. Emmert, and M. Galvan Pharmacology of the human metabolites of dolasetron, an antiemetic 5-HT3 receptor antagonist Drug Dev. Res. 34 1995 289 296
5. P.H. Boeijinga, M. Galvan, B.M. Baron, M.W. Dudley, B.W. Siegel, and A.L. Slone Characterization of the novel 5-HT3 antagonists MDL 73147EF (dolasetron mesilate) and MDL 74156 in NG108-15 neuroblastoma x glioma cells Eur. J. Pharmacol. 219 1992 9 13
6. C. Bountra, K. Bunce, T. Dale, C. Gardner, C. Jordan, D. Twissell, and P. Ward Antiemetic profile of a nonpeptide neurokinin-NK(1) receptor antagonist, CP-99,994 in ferrets Eur. J. Pharmacol. 249 1993 R3 R4
7. R.T. Brittain, A. Butler, I.H. Coates, D.H. Fortune, R. Hagan, J.M. Hill, D.C. Humber, P.P.A. Humphrey, S.J. Ireland, D. Jack, C.C. Jordan, A. Oxford, D.W. Straughan, and M.B. Tyers Communication Br. J. Pharmacol. 90 1987 87P
8. K.H. Buchheit, B. Costall, G. Engel, S.J. Gunning, R.J. Naylor, and B.P. Richardson 5-Hydroxytryptamine receptor antagonism by metoclopramide and ICS 205-930 in the guinea-pig leads to enhancement of contractions of stomach muscle strips induced by electrical field stimulation and facilitation of gastric emptying in-vivo J. Pharm. Pharmacol. 37 1985 664 667 (Pubitemid 15016379)
9. M.M. Chang, and S.E. Leeman Isolation of a sialogogic peptide from bovine hypothalamic tissue and its characterization as substance P J. Biol. Chem. 245 1970 4784 4790
10. R.D. Clark, A.B. Miller, J. Berger, D.B. Repke, K.K. Weinhardt, B.A. Kowalczyk, R.M. Eglen, D.W. Bonhaus, C.H. Lee, and A.D. Michel et al. 2-(Quinuclidin-3-yl)pyrido[4,3-b]indol-1-ones and isoquinolin-1-ones. Potent conformationally restricted 5-HT3 receptor antagonists J. Med. Chem. 36 1993 2645 2657 (Pubitemid 23294131)
11. M. Constenla 5-HT3 receptor antagonists for prevention of late acute-onset emesis Ann. Pharmacother. 38 2004 1683 1691 (Pubitemid 39297769)
12. L.X. Cubeddu, I.S. Hoffmann, N.T. Fuenmayor, and A.L. Finn Efficacy of ondansetron (GR 38032F) and the role of serotonin in cisplatin-induced nausea and vomiting N. Engl. J. Med. 322 1990 810 816 (Pubitemid 20094144)
13. N.A. Darmani, and A.P. Ray Evidence for a re-evaluation of the neurochemical and anatomical bases of chemotherapy-induced vomiting Chem. Rev. 109 2009 3158 3199
14. N.A. Darmani, Y. Wang, J. Abad, A.P. Ray, G.R. Thrush, and J. Ramirez Utilization of the least shrew as a rapid and selective screening model for the antiemetic potential and brain penetration of substance P and NK1 receptor antagonists Brain Res. 1214 2008 58 72
15. N.A. Darmani, J.L. Crim, J.J. Janoyan, J. Abad, and J. Ramirez A re-evaluation of the neurotransmitter basis of chemotherapy-induced immediate and delayed vomiting: evidence from the least shrew Brain Res. 1248 2009 40 58
16. N.A. Darmani, S. Chebolu, B. Amos, and T. Alkam Synergistic antiemetic interactions between serotonergic 5-HT(3) and tachykininergic NK(1)-receptor antagonists in the least shrew (Cryptotis parva) Pharmacol. Biochem. Behav. 99 2011 573 579
17. N.A. Darmani, D. Dey, S. Chebolu, B. Amos, R. Kandpal, and T. Alkam Cisplatin causes over-expression of tachykinin NK(1) receptors and increases ERK1/2- and PKA-phosphorylation during peak immediate- and delayed-phase emesis in the least shrew (Cryptotis parva) brainstem Eur. J. Pharmacol. 698 2013 161 169
18. P.H. De Mulder, C. Seynaeve, J.B. Vermorken, P.A. van Liessum, S. Mols-Jevdevic, E.L. Allman, P. Beranek, and J. Verweij Ondansetron compared with high-dose metoclopramide in prophylaxis of acute and delayed cisplatin-induced nausea and vomiting. A multicenter, randomized, double-blind, crossover study Ann. Intern. Med. 113 1990 834 840
19. O. Dery, K.A. Defea, and N.W. Bunnett Protein kinase C-mediated desensitization of the neurokinin 1 receptor Am. J. Physiol. Cell Physiol. 280 2001 C1097 C1106
20. M.C. Desai, S.L. Lefkowitz, P.F. Thadeio, K.P. Longo, and R.M. Snider Discovery of a potent substance P antagonist: recognition of the key molecular determinant J. Med. Chem. 35 1992 4911 4913 (Pubitemid 23030928)
21. R. Di Fabio, C. Griffante, G. Alvaro, G. Pentassuglia, D.A. Pizzi, D. Donati, T. Rossi, G. Guercio, M. Mattioli, Z. Cimarosti, C. Marchioro, S. Provera, L. Zonzini, D. Montanari, S. Melotto, P.A. Gerrard, D.G. Trist, E. Ratti, and M. Corsi Discovery process and pharmacological characterization of 2-(S)-(4-fluoro-2-methylphenyl)piperazine-1-carboxylic Acid [1-(R)-(3,5-bis- trifluoromethylphenyl)ethyl]methylamide (vestipitant) as a potent, selective, and orally active NK1 receptor antagonist J. Med. Chem. 52 2009 3238 3247
22. R. Di Fabio, G. Alvaro, C. Griffante, D.A. Pizzi, D. Donati, M. Mattioli, Z. Cimarosti, G. Guercio, C. Marchioro, S. Provera, L. Zonzini, D. Montanari, S. Melotto, P.A. Gerrard, D.G. Trist, E. Ratti, and M. Corsi Discovery and biological characterization of (2R,4S)-1â€Â-acetyl-N-{(1R)-1- [3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4, 4â€Â-bipiperidine-1-carboxamide as a new potent and selective neurokinin 1 (NK1) receptor antagonist clinical candidate J. Med. Chem. 54 2011 1071 1079
23. P. Eisenberg, J. Figueroa-Vadillo, R. Zamora, V. Charu, J. Hajdenberg, A. Cartmell, A. Macciocchi, and S. Grunberg Improved prevention of moderately emetogenic chemotherapy-induced nausea and vomiting with palonosetron, a pharmacologically novel 5-HT3 receptor antagonist: results of a phase III, single-dose trial versus dolasetron Cancer 98 2003 2473 2482 (Pubitemid 37466663)
24. M.B. Emerit, M. Riad, C.M. Fattaccini, and M. Hamon Characteristics of [14C]guanidinium accumulation in NG 108-15 cells exposed to serotonin 5-HT3 receptor ligands and substance P J. Neurochem. 60 1993 2059 2067 (Pubitemid 23148777)
25. G. Engberg, T.H. Svensson, S. Rosell, and K. Folkers A synthetic peptide as an antagonist of substance-P Nature 293 1981 222 223
26. TM) Antiemesis, version 1.2012. NCCNorg.
27. C.S. Fake, F.D. King, and G.J. Sanger Communications Br. J. Pharmacol. 91 1987 335P
28. P. Feyer, and K. Jordan Update and new trends in antiemetic therapy: the continuing need for novel therapies Ann. Oncol. 22 2011 30 38
29. P. Fludzinski, D.A. Evrard, W.E. Bloomquist, W.B. Lacefield, W. Pfeifer, N.D. Jones, J.B. Deeter, and M.L. Cohen Indazoles as indole bioisosteres: synthesis and evaluation of the tropanyl ester and amide of indazole-3- carboxylate as antagonists at the serotonin 5HT3 receptor J. Med. Chem. 30 1987 1535 1537 (Pubitemid 17135896)
30. T.M. Fong, S.A. Anderson, H. Yu, R.R. Huang, and C.D. Strader Differential activation of intracellular effector by two isoforms of human neurokinin-1 receptor Mol. Pharmacol. 41 1992 24 30
31. J.R. Fozard Poster communications Br. J. Pharmacol. 80 1983 466P
32. J.R. Fozard, and M.W. Gittos Poster communications Br. J. Pharmacol. 80 1983 511P
33. J.R. Fozard, and M. Host Poster communications Br. J. Pharmacol. 1982 77
34. J.R. Fozard, and A.A. Mobarok Blockade of neuronal tryptamine receptors by metoclopramide Eur. J. Pharmacol. 49 1978 109 112 (Pubitemid 9193629)
35. J.R. Fozard, A.T. Mobarok Ali, and G. Newgrosh Blockade of serotonin receptors on autonomic neurones by (-)-cocaine and some related compounds Eur. J. Pharmacol. 59 1979 195 210 (Pubitemid 10159511)
36. S.L. Freeman, J. Glatzle, C.S. Robin, M. Valdellon, C. Sternini, J.W. Sharp, and H.E. Raybould Ligand-induced 5-HT3 receptor internalization in enteric neurons in rat ileum Gastroenterology 131 2006 97 107 (Pubitemid 44040915)
37. O. Geling, and H.G. Eichler Should 5-hydroxytryptamine-3 receptor antagonists be administered beyond 24 h after chemotherapy to prevent delayed emesis? Systematic re-evaluation of clinical evidence and drug cost implications J. Clin. Oncol. 23 2005 1289 1294 (Pubitemid 46202287)
38. R. Gralla, M. Lichinitser, S. Van Der Vegt, H. Sleeboom, J. Mezger, C. Peschel, G. Tonini, R. Labianca, A. Macciocchi, and M. Aapro Palonosetron improves prevention of chemotherapy-induced nausea and vomiting following moderately emetogenic chemotherapy: results of a double-blind randomized phase III trial comparing single doses of palonosetron with ondansetron Ann. Oncol. 14 2003 1570 1577 (Pubitemid 37304615)
39. R.J. Gralla Metoclopramide. A review of antiemetic trials Drugs 25 1 1983 63 73 (Pubitemid 13195447)
40. R.J. Gralla, R.M. Navari, P.J. Hesketh, W. Popovic, J. Strupp, J. Noy, L. Einhorn, D. Ettinger, W. Bushnell, and C. Friedman Single-dose oral granisetron has equivalent antiemetic efficacy to intravenous ondansetron for highly emetogenic cisplatin-based chemotherapy J. Clin. Oncol. 16 1998 1568 1573 (Pubitemid 28175782)
41. J. Hainsworth, W. Harvey, K. Pendergrass, B. Kasimis, D. Oblon, G. Monaghan, D. Gandara, P. Hesketh, A. Khojasteh, and G. Harker et al. A single-blind comparison of intravenous ondansetron, a selective serotonin antagonist, with intravenous metoclopramide in the prevention of nausea and vomiting associated with high-dose cisplatin chemotherapy J. Clin. Oncol. 9 1991 721 728
42. J.J. Hale, S.G. Mills, M. MacCoss, S.K. Shah, H.B. Qi, D.J. Mathre, M.A. Cascieri, S. Sadowski, C.D. Strader, D.E. MacIntyre, and J.M. Metzger 2(S)-((3,5-bis(trifluoromethyl)benzyl)oxy)-3(S)-phenyl-4-((3-oxo-1,2,4-t riazol-5-yl)methyl)morpholine.1. A potent, orally active, morpholine-based human neurokinin-1 receptor antagonist J. Med. Chem. 39 1996 1760 1762
43. J.J. Hale, S.G. Mills, M. MacCoss, P.E. Finke, M.A. Cascieri, S. Sadowski, E. Ber, G.G. Chicchi, M. Kurtz, J. Metzger, G. Eiermann, N.N. Tsou, F.D. Tattersall, N.M.J. Rupniak, A.R. Williams, W. Rycroft, R. Hargreaves, and D.E. MacIntyre Structural optimization affording 2-(R)-(1-(R)-3,5- bis(trifluoromethyl)phenylethoxy)-3-(S)-(4-fluoro)pheny l-4-(3-oxo-1,2,4- triazol-5-yl)methylmorpholine, a potent, orally active, long-acting morpholine acetal human NK-1 receptor antagonist J. Med. Chem. 41 1998 4607 4614 (Pubitemid 28516459)
44. J.J. Hale, S.G. Mills, M. MacCoss, C.P. Dorn, P.E. Finke, R.J. Budhu, R.A. Reamer, S.E.W. Huskey, D. Luffer-Atlas, B.J. Dean, E.M. McGowan, W.P. Feeney, S.H.L. Chiu, M.A. Cascieri, G.G. Chicchi, M.M. Kurtz, S. Sadowski, E. Ber, F.D. Tattersall, N.M.J. Rupniak, A.R. Williams, W. Rycroft, R. Hargreaves, J.M. Metzger, and D.E. MacIntyre Phosphorylated morpholine acetal human neurokinin-1 receptor antagonists as water-soluble prodrugs J. Med. Chem. 43 2000 1234 1241 (Pubitemid 30173749)
45. R. Hargreaves, J.C.A. Ferreira, D. Hughes, J. Brands, J. Hale, B. Mattson, and S. Mills Development of aprepitant, the first neurokinin-1 receptor antagonist for the prevention of chemotherapy-induced nausea and vomiting Ann. N. Y. Acad. Sci. 1222 2011 40 48
46. T. Harrison, B.J. Williams, C.J. Swain, and R.G. Ball Piperidine-ether based hNK1 antagonists 1: determination of the relative and absolute stereochemical requirements Bioorg. Med. Chem. Lett. 4 1994 2545 2550 (Pubitemid 24342942)
47. T. Harrison, A.P. Owens, B.J. Williams, C.J. Swain, R. Baker, P.H. Hutson, S. Sadowski, and M.A. Cascieri Piperidine-ether based hNK1 antagonists 2: investigation of the effect of N-substitution Bioorg. Med. Chem. Lett. 5 1995 209 212
48. P.J. Hesketh Management of nausea and vomiting in cancer treatment: introduction, scope of the problem P.J. Hesketh, Management of Nausea and Vomiting in Cancer and Cancer Treatment 2005 Jones and Bartlett Publishers Sudbury, MA
49. P.J. Hesketh, S.M. Grunberg, R.J. Gralla, D.G. Warr, F. Roila, R. de Wit, S.P. Chawla, A.D. Carides, J. Ianus, M.E. Elmer, J.K. Evans, K. Beck, S. Reines, and K.J. Horgan The oral neurokinin-1 antagonist aprepitant for the prevention of chemotherapy-induced nausea and vomiting: a multinational, randomized, double-blind, placebo-controlled trial in patients receiving high-dose cisplatin - the aprepitant protocol 052 study group J. Clin. Oncol. 21 2003 4112 4119 (Pubitemid 46606178)
50. P.J. Hesketh, S. Van Belle, M. Aapro, F.D. Tattersall, R.J. Naylor, R. Hargreaves, A.D. Carides, J.K. Evans, and K.J. Horgan Differential involvement of neurotransmitters through the time course of cisplatin-induced emesis as revealed by therapy with specific receptor antagonists Eur. J. Cancer 39 2003 1074 1080 (Pubitemid 36555864)
51. M.F. Hibert, R. Hoffmann, R.C. Miller, and A.A. Carr Conformation- activity relationship study of 5-HT3 receptor antagonists and a definition of a model for this receptor site J. Med. Chem. 33 1990 1594 1600 (Pubitemid 20180616)
52. G.M. Higa, M.L. Auber, R. Altaha, D. Piktel, S. Kurian, G. Hobbs, and K. Landreth 5-Hydroxyindoleacetic acid and substance P profiles in patients receiving emetogenic chemotherapy J. Oncol. Pharm. Pract. 12 2006 201 209 (Pubitemid 46091933)
53. T. Hoffmann, M. Bos, H. Stadler, P. Schnider, W. Hunkeler, T. Godel, G. Galley, T.M. Ballard, G.A. Higgins, S.M. Poli, and A.J. Sleight Design and synthesis of a novel, achiral class of highly potent and selective, orally active neurokinin-1 receptor antagonists Bioorg. Med. Chem. Lett. 16 2006 1362 1365 (Pubitemid 43143023)
54. P.J. Hornby Central neurocircuitry associated with emesis Am. J. Med. 111 8A 2001 106S 112S (Pubitemid 34032001)
55. W. Howson, J. Hodgson, R. Richardson, L. Walton, S. Guard, and K. Watling An SAR study for the nonpeptide substance-P receptor (NK1) antagonist, CP-96,345 Bioorg. Med. Chem. Lett. 2 1992 559 564
56. W.P. Hu, X.H. You, B.C. Guan, L.Q. Ru, J.G. Chen, and Z.W. Li Substance P potentiates 5-HT3 receptor-mediated current in rat trigeminal ganglion neurons Neurosci. Lett. 365 2004 147 152
57. J.M. Humphrey Medicinal chemistry of selective neurokinin-1 antagonists Curr. Top. Med. Chem. 3 2003 1423 1435
58. F.D. King, B.J. Jones, and G.J. Sanger 5-Hydroxytryptamine-3 Receptor Antagonists 1994 CRC Press
59. M.G. Kris, S.M. Grunberg, R.J. Gralla, L. Baltzer, S.A. Zaretsky, D. Lifsey, L.B. Tyson, L. Schmidt, and W.F. Hahne Dose-ranging evaluation of the serotonin antagonist dolasetron mesylate in patients receiving high-dose cisplatin J. Clin. Oncol. 12 1994 1045 1049 (Pubitemid 24145335)
60. C.M. Lee, N.J. Campbell, B.J. Williams, and L.L. Iversen Multiple tachykinin binding sites in peripheral tissues and in brain Eur. J. Pharmacol. 130 1986 209 217 (Pubitemid 17193205)
61. L.E. Limbird Cell Surface Receptors: A Short Course on Theory and Methods third ed. 2005 Springer
62. J.W. Lin, W. Ju, K. Foster, S.H. Lee, G. Ahmadian, M. Wyszynski, Y.T. Wang, and M. Sheng Distinct molecular mechanisms and divergent endocytotic pathways of AMPA receptor internalization Nat. Neurosci. 3 2000 1282 1290
63. J.A. Lowe, S.E. Drozda, R.M. Snider, K.P. Longo, S.H. Zorn, J. Morrone, E.R. Jackson, S. McLean, and D.K. Bryce The discovery of (2S,3S)-cis-2- (diphenylmethyl)-N-[(2-methoxyphenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine as a novel, nonpeptide substance P antagonist J. Med. Chem. 35 1992 2591 2600
64. M. Marty, P. Pouillart, S. Scholl, J.P. Droz, M. Azab, N. Brion, E. Pujade-Lauraine, B. Paule, D. Paes, and J. Bons Comparison of the 5-hydroxytryptamine3 (serotonin) antagonist ondansetron (GR 38032F) with high-dose metoclopramide in the control of cisplatin-induced emesis N. Engl. J. Med. 322 1990 816 821 (Pubitemid 20094145)
65. M. Minami, T. Endo, H. Yokota, T. Ogawa, M. Nemoto, N. Hamaue, M. Hirafuji, M. Yoshioka, A. Nagahisa, and P.L. Andrews Effects of CP-99, 994, a tachykinin NK(1) receptor antagonist, on abdominal afferent vagal activity in ferrets: evidence for involvement of NK(1) and 5-HT(3) receptors Eur. J. Pharmacol. 428 2001 215 220 (Pubitemid 33000143)
66. W.D. Miner, and G.J. Sanger Inhibition of cisplatin-induced vomiting by selective 5-hydroxytryptamine M-receptor antagonism Br. J. Pharmacol. 88 1986 497 499 (Pubitemid 16066912)
67. R.M. Navari Fosaprepitant: a neurokinin-1 receptor antagonist for the prevention of chemotherapy-induced nausea and vomiting Expert Rev. Anticancer Ther. 8 2008 1733 1742
68. D.G. Payan Neuropeptides and inflammation: the role of substance P Annu. Rev. Med. 40 1989 341 352 (Pubitemid 19145362)
69. E.A. Perez, P. Hesketh, J. Sandbach, J. Reeves, S. Chawla, M. Markman, J. Hainsworth, W. Bushnell, and C. Friedman Comparison of single-dose oral granisetron versus intravenous ondansetron in the prevention of nausea and vomiting induced by moderately emetogenic chemotherapy: a multicenter, double-blind, randomized parallel study J. Clin. Oncol. 16 1998 754 760 (Pubitemid 28135625)
70. L.H. Pheng, Y. Dumont, A. Fournier, J.G. Chabot, A. Beaudet, and R. Quirion Agonist- and antagonist-induced sequestration/internalization of neuropeptide Y Y1 receptors in HEK293 cells Br. J. Pharmacol. 139 2003 695 704 (Pubitemid 36819596)
71. S. Poli-Bigelli, J. Rodrigues-Pereira, A.D. Carides, Ma, G. Julie, K. Eldridge, A. Hipple, J.K. Evans, K.J. Horgan, and F. Lawson Addition of the neurokinin 1 receptor antagonist aprepitant to standard antiemetic therapy improves control of chemotherapy-induced nausea and vomiting. Results from a randomized, double-blind, placebo-controlled trial in Latin America Cancer 97 2003 3090 3098 (Pubitemid 36676265)
72. L. Quartara, and C.A. Maggi The tachykinin NK1 receptor. Part I: Ligands and mechanisms of cellular activation Neuropeptides 31 1997 537 563 (Pubitemid 28037471)
73. L. Quartara, and C.A. Maggi The tachykinin NK1 receptor. Part I: Ligands and mechanisms of cellular activation Neuropeptides 31 1997 537 563 (Pubitemid 28037471)
74. A.P. Ray, S. Chebolu, J. Ramirez, and N.A. Darmani Ablation of least shrew central neurokinin NK1 receptors reduces GR73632-induced vomiting Behav. Neurosci. 123 2009 701 706
75. G. Reiser, and B. Hamprecht Substance P and serotonin act synergistically to activate a cation permeability in a neuronal cell line Brain Res. 479 1989 40 48 (Pubitemid 19030911)
76. B.P. Richardson, G. Engel, P. Donatsch, and P.A. Stadler Identification of serotonin M-receptor subtypes and their specific blockade by a new class of drugs Nature 316 1985 126 131 (Pubitemid 15073674)
77. J.P. Rizzi, A.A. Nagel, T. Rosen, S. McLean, and T. Seeger An initial three-component pharmacophore for specific serotonin-3 receptor ligands J. Med. Chem. 33 1990 2721 2725 (Pubitemid 20312134)
78. E.S.M. Rocha, J.R. Valle, and P. Picarelli A pharmacological analysis of the mode of action of serotonin (5-hydroxytryptamine) upon the guinea-pig ileum Br. J. Pharmacol. Chemother. 8 1953 378 388
79. B.F. Roettger, D. Ghanekar, R. Rao, C. Toledo, J. Yingling, D. Pinon, and L.J. Miller Antagonist-stimulated internalization of the G protein-coupled cholecystokinin receptor Mol. Pharmacol. 51 1997 357 362 (Pubitemid 27118469)
80. F. Roila, J. Herrstedt, M. Aapro, R.J. Gralla, L.H. Einhorn, E. Ballatori, E. Bria, R.A. Clark-Snow, B.T. Espersen, P. Feyer, S.M. Grunberg, P.J. Hesketh, K. Jordan, M.G. Kris, E. Maranzano, A. Molassiotis, G. Morrow, I. Olver, B.L. Rapoport, C. Rittenberg, M. Saito, M. Tonato, and D. Warr Guideline update for MASCC and ESMO in the prevention of chemotherapy- and radiotherapy-induced nausea and vomiting: results of the Perugia consensus conference Ann. Oncol. 21 Suppl. 5 2010 v232 v243
81. C. Rojas, M. Stathis, A.G. Thomas, E.B. Massuda, J. Alt, J. Zhang, E. Rubenstein, S. Sebastiani, S. Cantoreggi, S.H. Snyder, and B. Slusher Palonosetron exhibits unique molecular interactions with the 5-HT3 receptor Anesth. Analg. 107 2008 469 478
82. C. Rojas, Y. Li, J. Zhang, M. Stathis, J. Alt, A.G. Thomas, S. Cantoreggi, S. Sebastiani, C. Pietra, and B.S. Slusher The antiemetic 5-HT3 receptor antagonist palonosetron inhibits substance P-mediated responses in vitro and in vivo J. Pharmacol. Exp. Ther. 335 2010 362 368
83. C. Rojas, A.G. Thomas, J. Alt, M. Stathis, J. Zhang, E.B. Rubenstein, S. Sebastiani, S. Cantoreggi, and B.S. Slusher Palonosetron triggers 5-HT(3) receptor internalization and causes prolonged inhibition of receptor function Eur. J. Pharmacol. 626 2010 193 199
84. B. Rosenberg, L. VanCamp, J.E. Trosko, and V.H. Mansour Platinum compounds: a new class of potent antitumour agents Nature 222 1969 385 386
85. J.A. Rudd, and P.L.R. Andrews Mechanisms of acute, delayed, and anticipatory emesis induced by anticancer therapies P.J. Hesketh, Management of Nausea and Vomiting in Cancer and Cancer Treatment 2005 Jones and Bartlett Publishers Sudbury
86. S.M. Sagar The current role of anti-emetic drugs in oncology: a recent revolution in patient symptom control Cancer Treat. Rev. 18 1991 95 135
87. M. Saito, K. Aogi, I. Sekine, H. Yoshizawa, Y. Yanagita, H. Sakai, K. Inoue, C. Kitagawa, T. Ogura, and S. Mitsuhashi Palonosetron plus dexamethasone versus granisetron plus dexamethasone for prevention of nausea and vomiting during chemotherapy: a double-blind, double-dummy, randomised, comparative phase III trial Lancet Oncol. 10 2009 115 124
88. 2+ channels Eur. J. Pharmacol. 219 1992 491 492
89. L. Schwartzberg, J. Jackson, G. Jain, S. Balu, and D. Buchner Impact of 5-HT(3) RA selection within triple antiemetic regimens on uncontrolled highly emetogenic chemotherapy-induced nausea/vomiting Expert Rev. Pharmacoecon. Outcomes Res. 11 2011 481 488
90. E.M. Seward, C.J. Swain, K.J. Merchant, S.N. Owen, V. Sabin, M.A. Cascieri, S. Sadowski, C. Strader, and R. Baker Quinuclidine-based NK-1 antagonists. 1. 3-benzyloxy-1-azabicyclo[2.2.2]octanes Bioorg. Med. Chem. Lett. 3 1993 1361 1366
91. R.M. Snider, J.W. Constantine, J.A.L. Iii, K.P. Longo, W.S. Lebel, H.A. Woody, S.E. Drozda, M.C. Desai, F.J. Vinick, R.W. Spencer, and H.-J. Hess A potent nonpeptide antagonist of the substance P (NK$-1$) receptor Science 251 1991 435 437
92. S.M. Sorensen, T.M. Humphreys, and M.G. Palfreyman Effect of acute and chronic MDL 73,147EF, a 5-HT3 receptor antagonist, on A9 and A10 dopamine neurons Eur. J. Pharmacol. 163 1989 115 118 (Pubitemid 19107549)
93. M. Soukop, B. McQuade, E. Hunter, A. Stewart, S. Kaye, J. Cassidy, D. Kerr, S. Khanna, J. Smyth, and R. Coleman et al. Ondansetron compared with metoclopramide in the control of emesis and quality of life during repeated chemotherapy for breast cancer Oncology 49 1992 295 304
94. M. Stathis, C. Pietra, C. Rojas, and B.S. Slusher Inhibition of substance P-mediated responses in NG108-15 cells by netupitant and palonosetron exhibit synergistic effects Eur. J. Pharmacol. 689 2012 25 30
95. R. Stoltz, J.C. Cyong, A. Shah, and S. Parisi Pharmacokinetic and safety evaluation of palonosetron, a 5-hydroxytryptamine-3 receptor antagonist, in U.S. and Japanese healthy subjects J. Clin. Pharmacol. 44 2004 520 531 (Pubitemid 38509721)
96. H. Sun, X.Q. Hu, E.M. Moradel, F.F. Weight, and L. Zhang Modulation of 5-HT3 receptor-mediated response and trafficking by activation of protein kinase C J. Biol. Chem. 278 2003 34150 34157 (Pubitemid 37553256)
97. C.J. Swain, E.M. Seward, V. Sabin, S. Owen, R. Baker, M.A. Cascieri, S. Sadowski, C. Strader, and R.G. Ball Quinuclidine based NK-1 antagonists 2: determination of the absolute stereochemical requirements Bioorg. Med. Chem. Lett. 3 1993 1703 1706 (Pubitemid 23270215)
98. S.J. Van Belle, L. Stamatakis, H. Bleiberg, V.F. Cocquyt, J. Michel, and K.M. de Bruijn Dose-finding study of tropisetron in cisplatin-induced nausea and vomiting Ann. Oncol. 5 1994 821 825 (Pubitemid 24341875)
99. J. Verweij, R. de Wit, and P.H. de Mulder Optimal control of acute cisplatin-induced emesis Oncology 53 Suppl. 1 1996 56 64 (Pubitemid 26335151)
100. U.S. Von Euler, and J.H. Gaddum An unidentified depressor substance in certain tissue extracts J. Physiol. 72 1931 74 87
101. E.H. Wong, R. Clark, E. Leung, D. Loury, D.W. Bonhaus, L. Jakeman, H. Parnes, R.L. Whiting, and R.M. Eglen The interaction of RS 25259-197, a potent and selective antagonist, with 5-HT3 receptors, in vitro Br. J. Pharmacol. 114 1995 851 859
102. X. Wu, J. Fan, C. Owyang, and Y. Li Upregulation of vagal NK1 receptor by cisplatin facilitates the interaction of substance P and serotoninin the vagal afferent neurons: implication in the emesis related to chemotherapy Gastroenterology 136 Suppl. 2009 A98 A99
103. D. Yan, M.K. Schulte, K.E. Bloom, and M.M. White Structural features of the ligand-binding domain of the serotonin 5HT3 receptor J. Biol. Chem. 274 1999 5537 5541 (Pubitemid 29109202)
104. S.N. Young Mechanism of decline in rat brain 5-hydroxytryptamine after induction of liver tryptophan pyrrolase by hydrocortisone: roles of tryptophan catabolism and kynurenine synthesis Br. J. Pharmacol. 74 1981 695 700 (Pubitemid 12239839)
105. R.D. Youssefyeh, H.F. Campbell, J.E. Airey, S. Klein, M. Schnapper, M. Powers, R. Woodward, W. Rodriguez, S. Golec, and W. Studt et al. Development of high-affinity 5-HT3 receptor antagonists. 2. Two novel tricyclic benzamides J. Med. Chem. 35 1992 903 911
106. R.D. Youssefyeh, H.F. Campbell, S. Klein, J.E. Airey, P. Darkes, M. Powers, M. Schnapper, K. Neuenschwander, L.R. Fitzpatrick, and C.E. Pendley et al. Development of high-affinity 5-HT3 receptor antagonists. 1. Initial structure-activity relationship of novel benzamides J. Med. Chem. 35 1992 895 903