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Histamine H3 Receptor as a Drug Discovery Target

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Chemical Research, Merck Research Laboratories, 2015 Galloping Hill Road, Kenilworth, New Jersey 07033, United States
*To whom correspondence should be addressed. Phone: 1-908-740-3909. Fax: 1-908-740-7152. E-mail: [email protected]
Cite this: J. Med. Chem. 2011, 54, 1, 26–53
Publication Date (Web):November 9, 2010
https://doi.org/10.1021/jm100064d
Copyright © 2010 American Chemical Society

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    Details of the H3 receptor signaling pathways (summarized in Figure 4) and details of the clinical trials targeting H3 receptor (as listed on www.clinicaltrials.gov). This material is available free of charge via the Internet at http://pubs.acs.org.

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    32. Infant Sagayaraj Ravhe, Arunkumar Krishnan, Narayanan Manoj. Evolutionary history of histamine receptors: Early vertebrate origin and expansion of the H3-H4 subtypes. Molecular Phylogenetics and Evolution 2021, 154 , 106989. https://doi.org/10.1016/j.ympev.2020.106989
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    45. Nermin Eissa, Sheikh Azimullah, Petrilla Jayaprakash, Richard L. Jayaraj, David Reiner, Shreesh K. Ojha, Rami Beiram, Holger Stark, Dorota Łażewska, Katarzyna Kieć-Kononowicz, Bassem Sadek. The dual-active histamine H3 receptor antagonist and acetylcholine esterase inhibitor E100 ameliorates stereotyped repetitive behavior and neuroinflammmation in sodium valproate induced autism in mice. Chemico-Biological Interactions 2019, 312 , 108775. https://doi.org/10.1016/j.cbi.2019.108775
    46. Nakisa Ghamari, Omid Zarei, José-Antonio Arias-Montaño, David Reiner, Siavoush Dastmalchi, Holger Stark, Maryam Hamzeh-Mivehroud. Histamine H3 receptor antagonists/inverse agonists: Where do they go?. Pharmacology & Therapeutics 2019, 200 , 69-84. https://doi.org/10.1016/j.pharmthera.2019.04.007
    47. David Schaller, Stefanie Hagenow, Holger Stark, Gerhard Wolber, . Ligand-guided homology modeling drives identification of novel histamine H3 receptor ligands. PLOS ONE 2019, 14 (6) , e0218820. https://doi.org/10.1371/journal.pone.0218820
    48. Anne C. Baakman, Rob Zuiker, Joop M.A. van Gerven, Nicholas Gross, Ronghua Yang, Michael Fetell, Ari Gershon, Yossi Gilgun‐Sherki, Edward Hellriegel, Ofer Spiegelstein. Central nervous system effects of the histamine‐3 receptor antagonist CEP‐26401, in comparison with modafinil and donepezil, after a single dose in a cross‐over study in healthy volunteers. British Journal of Clinical Pharmacology 2019, 85 (5) , 970-985. https://doi.org/10.1111/bcp.13885
    49. Nakisa Ghamari, Omid Zarei, David Reiner, Siavoush Dastmalchi, Holger Stark, Maryam Hamzeh‐Mivehroud. Histamine H 3 receptor ligands by hybrid virtual screening, docking, molecular dynamics simulations, and investigation of their biological effects. Chemical Biology & Drug Design 2019, 93 (5) , 832-843. https://doi.org/10.1111/cbdd.13471
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    54. Dorota Łażewska, Katarzyna Kieć-Kononowicz. Progress in the development of histamine H 3 receptor antagonists/inverse agonists: a patent review (2013-2017). Expert Opinion on Therapeutic Patents 2018, 28 (3) , 175-196. https://doi.org/10.1080/13543776.2018.1424135
    55. Anna Affini, Stefanie Hagenow, Aleksandra Zivkovic, Jose Marco-Contelles, Holger Stark. Novel indanone derivatives as MAO B/H3R dual-targeting ligands for treatment of Parkinson’s disease. European Journal of Medicinal Chemistry 2018, 148 , 487-497. https://doi.org/10.1016/j.ejmech.2018.02.015
    56. Roman Guryn, Marek Staszewski, Anna Stasiak, Daniel McNaught Flores, Wiesława Fogel, Rob Leurs, Krzysztof Walczyński. Non-Imidazole Histamine H3 Ligands. Part VII. Synthesis, In Vitro and In Vivo Characterization of 5-Substituted-2-thiazol-4-n-propylpiperazines. Molecules 2018, 23 (2) , 326. https://doi.org/10.3390/molecules23020326
    57. Jian Xin, Min Hu, Qian Liu, Tian Tai Zhang, Dong Mei Wang, Song Wu. Design, synthesis, and biological evaluation of novel iso-flavones derivatives as H 3 R antagonists. Journal of Enzyme Inhibition and Medicinal Chemistry 2018, 33 (1) , 1545-1553. https://doi.org/10.1080/14756366.2018.1509212
    58. Ida Osborn Frandsen, Michael W. Boesgaard, Kimberley Fidom, Alexander S. Hauser, Vignir Isberg, Hans Bräuner-Osborne, Petrine Wellendorph, David E. Gloriam. Identification of Histamine H3 Receptor Ligands Using a New Crystal Structure Fragment-based Method. Scientific Reports 2017, 7 (1) https://doi.org/10.1038/s41598-017-05058-w
    59. Emanuele Amata, Agostino Marrazzo, Maria Dichiara, Maria N. Modica, Loredana Salerno, Orazio Prezzavento, Giovanni Nastasi, Antonio Rescifina, Giuseppe Romeo, Valeria Pittalà. Heme Oxygenase Database (HemeOxDB) and QSAR Analysis of Isoform 1 Inhibitors. ChemMedChem 2017, 12 (22) , 1873-1881. https://doi.org/10.1002/cmdc.201700321
    60. Dorota Łażewska, Maria Kaleta, J. Stephan Schwed, Tadeusz Karcz, Szczepan Mogilski, Gniewomir Latacz, Agnieszka Olejarz, Agata Siwek, Monika Kubacka, Annamaria Lubelska, Ewelina Honkisz, Jadwiga Handzlik, Barbara Filipek, Holger Stark, Katarzyna Kieć-Kononowicz. Biphenyloxy-alkyl-piperidine and azepane derivatives as histamine H3 receptor ligands. Bioorganic & Medicinal Chemistry 2017, 25 (20) , 5341-5354. https://doi.org/10.1016/j.bmc.2017.07.058
    61. Weiwei Hu, Zhong Chen. The roles of histamine and its receptor ligands in central nervous system disorders: An update. Pharmacology & Therapeutics 2017, 175 , 116-132. https://doi.org/10.1016/j.pharmthera.2017.02.039
    62. Fereshteh Shiri, Maryam Teymoori. In silico approaches to explore structure of new GPR 119 agonists for treatment of type 2 diabetes mellitus. Medicinal Chemistry Research 2017, 26 (5) , 947-961. https://doi.org/10.1007/s00044-017-1808-y
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    66. Bassem Sadek, Ali Saad, Adel Sadeq, Fakhreya Jalal, Holger Stark. Histamine H3 receptor as a potential target for cognitive symptoms in neuropsychiatric diseases. Behavioural Brain Research 2016, 312 , 415-430. https://doi.org/10.1016/j.bbr.2016.06.051
    67. Bassem Sadek, Nadia Khan, Fouad H. Darras, Steffen Pockes, Michael Decker. The dual-acting AChE inhibitor and H3 receptor antagonist UW-MD-72 reverses amnesia induced by scopolamine or dizocilpine in passive avoidance paradigm in rats. Physiology & Behavior 2016, 165 , 383-391. https://doi.org/10.1016/j.physbeh.2016.08.022
    68. Wilber Montejo-López, Nayeli Rivera-Ramírez, Juan Escamilla-Sánchez, Ubaldo García-Hernández, José-Antonio Arias-Montaño. Heterologous, PKC-Mediated Desensitization of Human Histamine H3 Receptors Expressed in CHO-K1 Cells. Neurochemical Research 2016, 41 (9) , 2415-2424. https://doi.org/10.1007/s11064-016-1954-5
    69. Robert L. Hudkins, John A. Gruner, Rita Raddatz, Joanne R. Mathiasen, Lisa D. Aimone, Michael J. Marino, Edward R. Bacon, Michael Williams, Mark A. Ator. 3-(1′-Cyclobutylspiro[4H-1,3-benzodioxine-2,4′-piperidine]-6-yl)-5,5-dimethyl-1,4-dihydropyridazin-6-one (CEP-32215), a new wake-promoting histamine H3 antagonist/inverse agonist. Neuropharmacology 2016, 106 , 37-45. https://doi.org/10.1016/j.neuropharm.2015.09.025
    70. Bassem Sadek, Holger Stark. Cherry-picked ligands at histamine receptor subtypes. Neuropharmacology 2016, 106 , 56-73. https://doi.org/10.1016/j.neuropharm.2015.11.005
    71. Mohammad A. Khanfar, Anna Affini, Kiril Lutsenko, Katarina Nikolic, Stefania Butini, Holger Stark. Multiple Targeting Approaches on Histamine H3 Receptor Antagonists. Frontiers in Neuroscience 2016, 10 https://doi.org/10.3389/fnins.2016.00201
    72. B. Sadek, D. Łażewska, S. Hagenow, K. Kieć-Kononowicz, H. Stark. Histamine H3R Antagonists: From Scaffold Hopping to Clinical Candidates. 2016, 109-155. https://doi.org/10.1007/978-3-319-40308-3_5
    73. Ruben Vardanyan, Victor Hruby. Antihistamine Drugs. 2016, 247-263. https://doi.org/10.1016/B978-0-12-411492-0.00016-X
    74. Nadia Khan, Ali Saad, Syed M. Nurulain, Fouad H. Darras, Michael Decker, Bassem Sadek. The dual-acting H3 receptor antagonist and AChE inhibitor UW-MD-71 dose-dependently enhances memory retrieval and reverses dizocilpine-induced memory impairment in rats. Behavioural Brain Research 2016, 297 , 155-164. https://doi.org/10.1016/j.bbr.2015.10.022
    75. Guozheng Huang, Martin Nimczick, Michael Decker. Rational Modification of the Biological Profile of GPCR Ligands through Combination with Other Biologically Active Moieties. Archiv der Pharmazie 2015, 348 (8) , 531-540. https://doi.org/10.1002/ardp.201500079
    76. Pertti Panula, Paul L. Chazot, Marlon Cowart, Ralf Gutzmer, Rob Leurs, Wai L. S. Liu, Holger Stark, Robin L. Thurmond, Helmut L. Haas, . International Union of Basic and Clinical Pharmacology. XCVIII. Histamine Receptors. Pharmacological Reviews 2015, 67 (3) , 601-655. https://doi.org/10.1124/pr.114.010249
    77. Robert L. Hudkins, Nadine C. Becknell, Jacquelyn A. Lyons, Lisa D. Aimone, Mark Olsen, R. Curtis Haltiwanger, Joanne R. Mathiasen, Rita Raddatz, John A. Gruner. 3,4-Diaza-bicyclo[4.1.0]hept-4-en-2-one phenoxypropylamine analogs of irdabisant (CEP-26401) as potent histamine-3 receptor inverse agonists with robust wake-promoting activity. European Journal of Medicinal Chemistry 2015, 95 , 349-356. https://doi.org/10.1016/j.ejmech.2015.03.054
    78. Sankar Chatterjee. In search of potent histamine-3 receptor antagonists. Journal of King Saud University - Science 2015, 27 (2) , 189-192. https://doi.org/10.1016/j.jksus.2014.09.003
    79. Zhongli Gao, William J. Hurst, Daniel Hall, Ryan Hartung, William Reynolds, Jiesheng Kang, Raisa Nagorny, James A. Hendrix, Pascal G. George. Design and synthesis of a novel series of histamine H3 receptor antagonists through a scaffold hopping strategy. Bioorganic & Medicinal Chemistry 2015, 23 (3) , 429-438. https://doi.org/10.1016/j.bmc.2014.12.036
    80. Elemer Szabadi. Neuronal Networks Regulating Sleep and Arousal: Effect of Drugs. 2015, 25-70. https://doi.org/10.1007/978-3-319-11514-6_2
    81. Tadaho Nakamura, Takeo Yoshikawa, Fumito Naganuma, Attayeb Mohsen, Tomomitsu Iida, Yamato Miura, Akira Sugawara, Kazuhiko Yanai. Role of histamine H 3 receptor in glucagon‐secreting αTC1.6 cells. FEBS Open Bio 2015, 5 (1) , 36-41. https://doi.org/10.1016/j.fob.2014.12.001
    82. Katarina Nikolic, Danica Agbaba, Holger Stark. Pharmacophore modeling, drug design and virtual screening on multi-targeting procognitive agents approaching histaminergic pathways. Journal of the Taiwan Institute of Chemical Engineers 2015, 46 , 15-29. https://doi.org/10.1016/j.jtice.2014.09.017
    83. Yves P. Auberson, Thomas Troxler, Xuechun Zhang, Charles R. Yang, Markus Fendt, Dominik Feuerbach, Yu‐Chih Liu, Bharat Lagu, Andreas Lerchner, Mark Perrone, Lijun Lei, Chao Zhang, Chunxiu Wang, Tie‐Lin Wang, Mark G. Bock. Ergoline‐Derived Inverse Agonists of the Human H3 Receptor for the Treatment of Narcolepsy. ChemMedChem 2014, 9 (8) , 1683-1696. https://doi.org/10.1002/cmdc.201402055
    84. V Margaret Jackson, David A Price, Philip A Carpino. Investigational drugs in Phase II clinical trials for the treatment of obesity: implications for future development of novel therapies. Expert Opinion on Investigational Drugs 2014, 23 (8) , 1055-1066. https://doi.org/10.1517/13543784.2014.918952
    85. Katarina Nikolic, Slavica Filipic, Danica Agbaba, Holger Stark. Procognitive Properties of Drugs with Single and Multitargeting H 3 Receptor Antagonist Activities. CNS Neuroscience & Therapeutics 2014, 20 (7) , 613-623. https://doi.org/10.1111/cns.12279
    86. Kerstin Wingen, J. Stephan Schwed, Kathleen Isensee, Lilia Weizel, Aleksandra Živković, Dalibor Odazic, Holger Stark. Benzylpiperidine variations on histamine H3 receptor ligands for improved drug-likeness. Bioorganic & Medicinal Chemistry Letters 2014, 24 (10) , 2236-2239. https://doi.org/10.1016/j.bmcl.2014.03.098
    87. Christoph P. Czerner, Andreas Klos, Roland Seifert, Detlef Neumann. Histamine induces chemotaxis and phagocytosis in murine bone marrow-derived macrophages and RAW 264.7 macrophage-like cells via histamine H4-receptor. Inflammation Research 2014, 63 (3) , 239-247. https://doi.org/10.1007/s00011-013-0694-0
    88. Leonid I. Belen’kii, Yu. B. Evdokimenkova. The Literature of Heterocyclic Chemistry, Part XII, 2010–2011. 2014, 147-274. https://doi.org/10.1016/B978-0-12-420160-6.00004-5
    89. Iwona Masłowska‐Lipowicz, Krzysztof Walczyński. Structure–Activity Relationships of New 1‐substitutedmethyl‐4‐[5‐( N ‐methyl‐ N ‐propylamino)pentyloxy]piperidines and Selected 1‐[( N ‐substituted‐ N‐ methyl)‐3‐propyloxy]‐5‐( N ‐methy‐l‐ N ‐propyl)‐pentanediamines as H 3 ‐Antagonists. Chemical Biology & Drug Design 2014, 83 (1) , 106-118. https://doi.org/10.1111/cbdd.12206
    90. Andria L. Del Tredici, Jian-Nong Ma, Fabrice Piu, Ethan S. Burstein. Identification of the Antiarrhythmic Drugs Amiodarone and Lorcainide as Potent H3 Histamine Receptor Inverse Agonists. Journal of Pharmacology and Experimental Therapeutics 2014, 348 (1) , 116-124. https://doi.org/10.1124/jpet.113.208892
    91. Dorota Łażewska, Katarzyna Kieć-Kononowicz. New developments around histamine H 3 receptor antagonists/inverse agonists: a patent review (2010 – present). Expert Opinion on Therapeutic Patents 2014, 24 (1) , 89-111. https://doi.org/10.1517/13543776.2014.848197
    92. Shinya Harusawa, Koichi Sawada, Takuji Magata, Hiroki Yoneyama, Lisa Araki, Yoshihide Usami, Kouta Hatano, Kouichi Yamamoto, Daisuke Yamamoto, Atsushi Yamatodani. Synthesis and evaluation of N-alkyl-S-[3-(piperidin-1-yl)propyl]isothioureas: High affinity and human/rat species-selective histamine H3 receptor antagonists. Bioorganic & Medicinal Chemistry Letters 2013, 23 (23) , 6415-6420. https://doi.org/10.1016/j.bmcl.2013.09.052
    93. Zhongli Gao, William J. Hurst, Werngard Czechtizky, Daniel Hall, Nicolas Moindrot, Raisa Nagorny, Philippe Pichat, David Stefany, James A. Hendrix, Pascal G. George. Identification and profiling of 3,5-dimethyl-isoxazole-4-carboxylic acid [2-methyl-4-((2S,3′S)-2-methyl-[1,3′]bipyrrolidinyl-1′-yl)phenyl] amide as histamine H3 receptor antagonist for the treatment of depression. Bioorganic & Medicinal Chemistry Letters 2013, 23 (23) , 6269-6273. https://doi.org/10.1016/j.bmcl.2013.09.081
    94. Kerstin Wingen, Holger Stark. Scaffold variations in amine warhead of histamine H3 receptor antagonists. Drug Discovery Today: Technologies 2013, 10 (4) , e483-e489. https://doi.org/10.1016/j.ddtec.2013.07.001
    95. Qingbei Zeng, Stuart B. Rosenblum, Zhaoxia Yang, Yueheng Jiang, Kevin D. McCormick, Robert G. Aslanian, Luli Duguma, Joseph A. Kozlowski, Neng-Yang Shih, John A. Hey, Robert E. West, Walter A. Korfmacher, Michael Berlin, Christopher W. Boyce. Synthesis and SAR studies of benzimidazolone derivatives as histamine H3-receptor antagonists. Bioorganic & Medicinal Chemistry Letters 2013, 23 (21) , 6001-6003. https://doi.org/10.1016/j.bmcl.2013.08.012
    96. Manuel de Lera Ruiz, Junying Zheng, Michael Y. Berlin, Kevin D. McCormick, Robert G. Aslanian, Robert West, Joyce Hwa, Jean Lachowicz, Margaret van Heek. Bicyclic and tricyclic heterocycle derivatives as histamine H3 receptor antagonists for the treatment of obesity. Bioorganic & Medicinal Chemistry Letters 2013, 23 (21) , 6004-6009. https://doi.org/10.1016/j.bmcl.2013.08.013
    97. Yana Charlier, Christian Brabant, Maria Elisa Serrano, Yves Lamberty, Ezio Tirelli. The prototypical histamine H3 receptor inverse agonist thioperamide improves multiple aspects of memory processing in an inhibitory avoidance task. Behavioural Brain Research 2013, 253 , 121-127. https://doi.org/10.1016/j.bbr.2013.07.016
    98. Jeremy J. Edmunds. Anti‐Inflammatory and Immunomodulatory Drugs. 2013, 337-388. https://doi.org/10.1002/9781118354483.ch9
    99. Marek Staszewski, Krzysztof Walczyński. 1-Phenoxyalkyl-4-[(N,N-disubstitutedamino)alkyl]piperazine derivatives as non-imidazole histamine H3-antagonists. Medicinal Chemistry Research 2013, 22 (3) , 1287-1304. https://doi.org/10.1007/s00044-012-0090-2
    100. Derek Dunn, Rita Raddatz, Mark A. Ator, Edward R. Bacon, Sankar Chatterjee. From an Atypical Wake‐promoting Agent to Potent Histamine‐3 Receptor Inverse Agonists. Chemical Biology & Drug Design 2013, 81 (3) , 433-435. https://doi.org/10.1111/cbdd.12094
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