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Latest advances in the discovery of fatty acid amide hydrolase inhibitors

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Pages 509-522 | Published online: 14 Mar 2013

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Domenico Fazio, Emanuele Criscuolo, Alessandra Piccoli, Barbara Barboni, Filomena Fezza & Mauro Maccarrone. (2020) Advances in the discovery of fatty acid amide hydrolase inhibitors: what does the future hold?. Expert Opinion on Drug Discovery 15:7, pages 765-778.
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Carina Hasenoehrl, Martin Storr & Rudolf Schicho. (2017) Cannabinoids for treating inflammatory bowel diseases: where are we and where do we go?. Expert Review of Gastroenterology & Hepatology 11:4, pages 329-337.
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Jan Althaus, Theresa Hake, Walburga Hanekamp & Matthias Lehr. (2016) 1-(5-Carboxyindazol-1-yl)propan-2-ones as dual inhibitors of cytosolic phospholipase A2α and fatty acid amide hydrolase: bioisosteric replacement of the carboxylic acid moiety. Journal of Enzyme Inhibition and Medicinal Chemistry 31:sup1, pages 131-140.
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Mauro Maccarrone. (2015) Endocannabinoid signaling in female reproductive events: a potential therapeutic target?. Expert Opinion on Therapeutic Targets 19:11, pages 1423-1427.
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Alessio Lodola, Riccardo Castelli, Marco Mor & Silvia Rivara. (2015) Fatty acid amide hydrolase inhibitors: a patent review (2009 – 2014). Expert Opinion on Therapeutic Patents 25:11, pages 1247-1266.
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Joséphine Caruano, Marion Feledziak, Geoffray Labar, Catherine Michaux, Eric A. Perpète, Giulio G. Muccioli, Raphaël Robiette & Jacqueline Marchand-Brynaert. (2014) (S)-1-(Pent-4′-enoyl)-4-(hydroxymethyl)-azetidin-2-one derivatives as inhibitors of human fatty acid amide hydrolase (hFAAH): synthesis, biological evaluation and molecular modelling. Journal of Enzyme Inhibition and Medicinal Chemistry 29:5, pages 654-662.
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Filomena Fezza, Nicolina Mastrangelo & Mauro Maccarrone. 2023. Endocannabinoid Signaling. Endocannabinoid Signaling 225 232 .
Michael J. Telch, Caitlin M. Fischer, Eric D. Zaizar, Mikael Rubin & Santiago Papini. (2022) Use of Cannabidiol (CBD) oil in the treatment of PTSD: Study design and rationale for a placebo-controlled randomized clinical trial. Contemporary Clinical Trials 122, pages 106933.
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Eric D. Zaizar, Santiago Papini, Patrick O'Connor & Michael J. Telch. (2022) Impact of cannabidiol-rich hemp extract oil on reconsolidation disruption of naturalistic interoceptive aversive memory in humans: Protocol for a randomized clinical trial. Contemporary Clinical Trials 119, pages 106847.
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Lu Hou, Jian Rong, Ahmed Haider, Daisuke Ogasawara, Cassis Varlow, Michael A. Schafroth, Linjing Mu, Jiefeng Gan, Hao Xu, Christopher J. Fowler, Ming-Rong Zhang, Neil Vasdev, Simon Ametamey, Benjamin F. Cravatt, Lu Wang & Steven H. Liang. (2020) Positron Emission Tomography Imaging of the Endocannabinoid System: Opportunities and Challenges in Radiotracer Development. Journal of Medicinal Chemistry 64:1, pages 123-149.
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Emanuele Criscuolo, Maria Laura De Sciscio, Filomena Fezza & Mauro Maccarrone. (2020) In Silico and In Vitro Analysis of Major Cannabis-Derived Compounds as Fatty Acid Amide Hydrolase Inhibitors. Molecules 26:1, pages 48.
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Ewa Galaj & Zheng-Xiong Xi. (2020) Possible Receptor Mechanisms Underlying Cannabidiol Effects on Addictive-like Behaviors in Experimental Animals. International Journal of Molecular Sciences 22:1, pages 134.
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Stephanie R. Wilt, Mark Rodriguez, Thanh N. H. Le, Emily V. Baltodano, Adrian Salas & Stevan Pecic. (2020) Design, microwave‐assisted synthesis, biological evaluation and molecular modeling studies of 4‐phenylthiazoles as potent fatty acid amide hydrolase inhibitors. Chemical Biology & Drug Design 95:5, pages 534-547.
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Pan Han, Zhuo-Ya Mao, Ming Li, Chang-Mei Si, Bang-Guo Wei & Guo-Qiang Lin. (2020) Synthesis of Amide Enol Carbamates and Carbonates through Cu(OTf) 2 -Catalyzed Reactions of Ynamides with t -Butyl Carbamates/Carbonates . The Journal of Organic Chemistry 85:7, pages 4740-4752.
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Enrico Dainese, Sergio Oddi, Monica Simonetti, Annalaura Sabatucci, Clotilde B. Angelucci, Alice Ballone, Beatrice Dufrusine, Filomena Fezza, Gianni De Fabritiis & Mauro Maccarrone. (2020) The endocannabinoid hydrolase FAAH is an allosteric enzyme. Scientific Reports 10:1.
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Rati Kailash Prasad Tripathi. (2020) A perspective review on fatty acid amide hydrolase (FAAH) inhibitors as potential therapeutic agents. European Journal of Medicinal Chemistry 188, pages 111953.
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Florence I. Raynaud. 2020. Metabolomics for Biomedical Research. Metabolomics for Biomedical Research 159 199 .
Manjunath Lamani, Michael S. Malamas, Shrouq I. Farah, Vidyanand G. Shukla, Michael F. Almeida, Catherine M. Weerts, Joseph Anderson, JodiAnne T. Wood, Karen L.G. Farizatto, Ben A. Bahr & Alexandros Makriyannis. (2019) Piperidine and piperazine inhibitors of fatty acid amide hydrolase targeting excitotoxic pathology. Bioorganic & Medicinal Chemistry 27:23, pages 115096.
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Luke J. Ney, Allison Matthews, Raimondo Bruno & Kim L. Felmingham. (2019) Cannabinoid interventions for PTSD: Where to next?. Progress in Neuro-Psychopharmacology and Biological Psychiatry 93, pages 124-140.
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Eleni P. Papagianni & Carl W. Stevenson. (2019) Cannabinoid Regulation of Fear and Anxiety: an Update. Current Psychiatry Reports 21:6.
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Charlotte Wang, Jung-Ying Tzeng, Pei-Zhen Wu, Martin Preisig & Chuhsing Kate Hsiao. (2018) Reexamining Dis/Similarity-Based Tests for Rare-Variant Association with Case-Control Samples. Genetics 209:1, pages 105-113.
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Matthew E. Sloan, Joshua L. Gowin, Jia Yan, Melanie L. Schwandt, Primavera A. Spagnolo, Hui Sun, Colin A. Hodgkinson, David Goldman & Vijay A. Ramchandani. (2018) Severity of alcohol dependence is associated with the fatty acid amide hydrolase Pro129Thr missense variant. Addiction Biology 23:1, pages 474-484.
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Filomena Fezza, Monica Bari, Domenico Fazio & Mauro Maccarrone. 2018. Encyclopedia of Signaling Molecules. Encyclopedia of Signaling Molecules 1687 1696 .
Mauro Maccarrone. (2017) Metabolism of the Endocannabinoid Anandamide: Open Questions after 25 Years. Frontiers in Molecular Neuroscience 10.
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Pieter Okkerse, Guido Amerongen, Marieke L. Kam, Jasper Stevens, Richard P. Butt, Rachel Gurrell, Albert Dahan, Joop M. Gerven, Justin L. Hay & Geert Jan Groeneveld. (2017) The use of a battery of pain models to detect analgesic properties of compounds: a two‐part four‐way crossover study. British Journal of Clinical Pharmacology 83:5, pages 976-990.
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Stefan Zahov, David Garzinsky, Walburga Hanekamp & Matthias Lehr. (2017) 1-Heteroarylpropan-2-ones as inhibitors of fatty acid amide hydrolase: Studies on structure-activity relationships and metabolic stability. Bioorganic & Medicinal Chemistry 25:3, pages 825-837.
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Helmut Dahlhaus, Walburga Hanekamp & Matthias Lehr. (2017) (Indolylalkyl)piperidine carbamates as inhibitors of fatty acid amide hydrolase (FAAH). MedChemComm 8:3, pages 616-620.
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Natalia Battista & Mauro Maccarrone. 2017. The Endocannabinoid System. The Endocannabinoid System 1 23 .
Martin A. KatzmanMelissa FurtadoLeena Anand. (2016) Targeting the Endocannabinoid System in Psychiatric Illness. Journal of Clinical Psychopharmacology 36:6, pages 691-703.
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Mesut Bilgin, Petra Born, Filomena Fezza, Michael Heimes, Nicolina Mastrangelo, Nicolai Wagner, Carsten Schultz, Mauro Maccarrone, Suzanne Eaton, André Nadler, Matthias Wilm & Andrej Shevchenko. (2016) Lipid Discovery by Combinatorial Screening and Untargeted LC-MS/MS. Scientific Reports 6:1.
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Stephen Pawsey, Mike Wood, Helen Browne, Kirsteen Donaldson, Mark Christie & Steven Warrington. (2016) Safety, Tolerability and Pharmacokinetics of FAAH Inhibitor V158866: A Double-Blind, Randomised, Placebo-Controlled Phase I Study in Healthy Volunteers. Drugs in R&D 16:2, pages 181-191.
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Biao Chen, Sha-Sha Ge, Yuan-Chao Zhao, Chong Chen & Song Yang. (2016) Activity-based protein profiling: an efficient approach to study serine hydrolases and their inhibitors in mammals and microbes. RSC Advances 6:114, pages 113327-113343.
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Filomena Fezza, Nicolina Mastrangelo & Mauro Maccarrone. 2016. Endocannabinoid Signaling. Endocannabinoid Signaling 123 130 .
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Isabelle Boileau, Pablo M Rusjan, Belinda Williams, Esmaeil Mansouri, Romina Mizrahi, Vincenzo De Luca, Douglas S Johnson, Alan A Wilson, Sylvain Houle, Stephen J Kish & Junchao Tong. (2015) Blocking of Fatty Acid Amide Hydrolase Activity with PF-04457845 in Human Brain: A Positron Emission Tomography Study with the Novel Radioligand [ 11 C]CURB . Journal of Cerebral Blood Flow & Metabolism 35:11, pages 1827-1835.
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S Sadhasivam, X Zhang, V Chidambaran, J Mavi, V Pilipenko, T B Mersha, J Meller, K M Kaufman, L J Martin & J McAuliffe. (2015) Novel associations between FAAH genetic variants and postoperative central opioid-related adverse effects. The Pharmacogenomics Journal 15:5, pages 436-442.
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Charles S. Demmer & Lennart Bunch. (2015) Benzoxazoles and oxazolopyridines in medicinal chemistry studies. European Journal of Medicinal Chemistry 97, pages 778-785.
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Tom Sundermann, Jörg Fabian, Walburga Hanekamp & Matthias Lehr. (2015) 1-Heteroaryl-3-phenoxypropan-2-ones as inhibitors of cytosolic phospholipase A2α and fatty acid amide hydrolase: Effect of the replacement of the ether oxygen with sulfur and nitrogen moieties on enzyme inhibition and metabolic stability. Bioorganic & Medicinal Chemistry 23:10, pages 2579-2592.
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Zun-Yi Wang, Peiqing Wang, Cecilia J. Hillard & Dale E. Bjorling. (2014) Attenuation of Cystitis and Pain Sensation in Mice Lacking Fatty Acid Amide Hydrolase. Journal of Molecular Neuroscience 55:4, pages 968-976.
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Guy Griebel, Philippe Pichat, Sandra Beeské, Thibaud Leroy, Nicolas Redon, Agnès Jacquet, Dominique Françon, Lionel Bert, Luc Even, Mati Lopez-Grancha, Tatiana Tolstykh, Fangxian Sun, Qunyan Yu, Scott Brittain, Heike Arlt, Timothy He, Bailin Zhang, Dmitri Wiederschain, Thomas Bertrand, Jacques Houtmann, Alexey Rak, François Vallée, Nadine Michot, Franck Augé, Véronique Menet, Olivier E. Bergis, Pascal George, Patrick Avenet, Vincent Mikol, Michel Didier & Johanna Escoubet. (2015) Selective blockade of the hydrolysis of the endocannabinoid 2-arachidonoylglycerol impairs learning and memory performance while producing antinociceptive activity in rodents. Scientific Reports 5:1.
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Bill Lands. (2015) Omega-3 PUFAs Lower the Propensity for Arachidonic Acid Cascade Overreactions. BioMed Research International 2015, pages 1-8.
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Daniel R. Dempsey, Kristen A. Jeffries, Jason D. Bond, Anne-Marie Carpenter, Santiago Rodriguez-Ospina, Leonid Breydo, K. Kenneth Caswell & David J. Merkler. (2014) Mechanistic and Structural Analysis of Drosophila melanogaster Arylalkylamine N -Acetyltransferases . Biochemistry 53:49, pages 7777-7793.
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Jo?lle Nader, Cinzia Rapino, Benjamin Gennequin, Francois Chavant, Maureen Francheteau, Alexandros Makriyannis, Andrea Duranti, Mauro Maccarrone, Marcello Solinas & Nathalie Thiriet. (2014) Prior stimulation of the endocannabinoid system prevents methamphetamine-induced dopaminergic neurotoxicity in the striatum through activation of CB2 receptors. Neuropharmacology 87, pages 214-221.
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Filomena Fezza, Monica Bari, Rita Florio, Emanuela Talamonti, Monica Feole & Mauro Maccarrone. (2014) Endocannabinoids, Related Compounds and Their Metabolic Routes. Molecules 19:11, pages 17078-17106.
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Justin W. Hicks, Jun Parkes, Junchao Tong, Sylvain Houle, Neil Vasdev & Alan A. Wilson. (2014) Radiosynthesis and ex vivo evaluation of [11C-carbonyl]carbamate- and urea-based monoacylglycerol lipase inhibitors. Nuclear Medicine and Biology 41:8, pages 688-694.
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David BorsookRichard HargreavesChas BountraFrank Porreca. (2014) Lost but making progress—Where will new analgesic drugs come from?. Science Translational Medicine 6:249.
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Filomena Fezza & Mauro Maccarrone. 2014. Cannabinoids. Cannabinoids 53 94 .
Marta Baranowska-Kuczko, Hanna Koz?owska, Miros?aw Koz?owski, Eberhard Schlicker, Monika Kloza, Arkadiusz Sura?y?ski, Emilia Grz?da & Barbara Malinowska. (2014) Mechanisms of endothelium-dependent relaxation evoked by anandamide in isolated human pulmonary arteries. Naunyn-Schmiedeberg's Archives of Pharmacology 387:5, pages 477-486.
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Y. Nasser, M. Bashashati & C. N. Andrews. (2014) Toward modulation of the endocannabinoid system for treatment of gastrointestinal disease: FAAHster but not “higher”. Neurogastroenterology & Motility 26:4, pages 447-454.
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Dominik P. Waluk, Matthew R. Battistini, Daniel R. Dempsey, Emma K. Farrell, Kristen A. Jeffries, Perry Mitchell, Lucas W. Hernandez, Joshua C. McBride, David J. Merkler & Mary C. Hunt. 2014. Omega-3 Fatty Acids in Brain and Neurological Health. Omega-3 Fatty Acids in Brain and Neurological Health 87 107 .
Jayendra Z. Patel, Teija Parkkari, Tuomo Laitinen, Agnieszka A. Kaczor, Susanna M. Saario, Juha R. Savinainen, Dina Navia-Paldanius, Mariateresa Cipriano, Jukka Leppänen, Igor O. Koshevoy, Antti Poso, Christopher J. Fowler, Jarmo T. Laitinen & Tapio Nevalainen. (2013) Chiral 1,3,4-Oxadiazol-2-ones as Highly Selective FAAH Inhibitors. Journal of Medicinal Chemistry 56:21, pages 8484-8496.
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Guillermo Moreno-Sanz, Andrea Duranti, Laurin Melzig, Claudio Fiorelli, Gian Filippo Ruda, Giampiero Colombano, Paola Mestichelli, Silvano Sanchini, Andrea Tontini, Marco Mor, Tiziano Bandiera, Rita Scarpelli, Giorgio Tarzia & Daniele Piomelli. (2013) Synthesis and Structure–Activity Relationship Studies of O -Biphenyl-3-yl Carbamates as Peripherally Restricted Fatty Acid Amide Hydrolase Inhibitors . Journal of Medicinal Chemistry 56:14, pages 5917-5930.
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Michael J. Telch, Caitlin M. Fischer, Eric D. Zaizar, Mikael Rubin & Santiago Papini. (2022) Use of Cannabidiol (CBD) Oil in the Treatment of PTSD: Study Design and Rationale for a Placebo-Controlled Randomized Clinical Trial. SSRN Electronic Journal.
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Eric D. Zaizar, Santiago Papini, Patrick O’Connor & Michael J. Telch. (2022) Impact of Cannabidiol-Rich Hemp Extract Oil on Reconsolidation Disruption of Naturalistic Interoceptive Aversive Memory in Humans: Protocol for a Randomized Clinical Trial. SSRN Electronic Journal.
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