Benzylamides and piperazinoarylamides of ibuprofen as fatty acid amide hydrolase inhibitors

References

• Di Marzo V. New approaches and challenges to targeting the endocannabinoid system. Nat Rev Drug Discov 2018;17:623–39.
   PubMed Web of Science ®Google Scholar
• Palermo G, Rothlisberger U, Cavalli A, De Vivo M. Computational insights into function and inhibition of fatty acid amide hydrolase. Eur J Med Chem 2015;91:15–26.
   PubMed Web of Science ®Google Scholar
• Bracey M, Hanson M, Masuda K, et al. Structural adaptions in a membrane enzyme that terminates endocannabinoid signaling. Science 2002;298:1793–6.
   PubMed Web of Science ®Google Scholar
• McKinney MK, Cravatt BF. Structure and function of fatty acid amide hydrolase. Annu Rev Biochem 2005;74:411–32.
   PubMed Web of Science ®Google Scholar
• Tuo W, Leleu-Chavain N, Spencer J, et al. Therapeutic potential of fatty acid amide hydrolase, monoacylglycerol lipase, and n-acylethanolamine acid amidase inhibitors. J Med Chem 2017;60:4–46.
   PubMed Web of Science ®Google Scholar
• Kathuria S, Gaetani S, Fegley D, et al. Modulation of anxiety through blockade of anandamide hydrolysis. Nat Med 2003;9:76–81.
   PubMed Web of Science ®Google Scholar
• Justinova Z, Mangieri R, Bortolato M, et al. Fatty acid amide hydrolase inhibition heightens anandamide signaling without producing reinforcing effects in primates. Biol Psychiat 2008;64:930–7.
   PubMed Web of Science ®Google Scholar
• Li GL, Winter H, Arends R, et al. Assessment of the pharmacology and tolerability of pf-04457845, an irreversible inhibitor of fatty acid amide hydrolase-1, in healthy subjects. Br J Clin Pharmacol 2012;73:706–16.
   PubMed Web of Science ®Google Scholar
• Pawsey S, Wood M, Browne H, et al. Safety, tolerability and pharmacokinetics of FAAH inhibitor v158866: a double-blind, randomised, placebo-controlled phase I study in healthy volunteers. Drugs R D 2016;16:181–91.
   PubMed Web of Science ®Google Scholar
• Wagenlehner FME, van Till JWO, Houbiers JGA, et al. Fatty acid amide hydrolase inhibitor treatment in men with chronic prostatitis/chronic pelvic pain syndrome: an adaptive double-blind, randomized controlled trial. Urology 2017;103:191–7.
   PubMed Web of Science ®Google Scholar
• van Esbroeck ACM, Janssen APA, Cognetta AB III, et al. Activity-based protein profiling reveals off-target proteins of the FAAH inhibitor BIA 10-2474. Science 2017;356:1084–7.
   PubMed Web of Science ®Google Scholar
• US Food and Drug Administration. FDA works with regulatory partners to understand French-based Biotrial phase 1 clinical study. 22 January 2016. Retrieved 23 January 2016. https://www.fda.gov/Drugs/DrugSafety/ucm482740.htm
   Google Scholar
• Huggins JP, Smart TS, Langman S, et al. An efficient randomised, placebo-controlled clinical trial with the irreversible fatty acid amide hydrolase-1 inhibitor pf-04457845, which modulates endocannabinoids but fails to induce effective analgesia in patients with pain due to osteoarthritis of the knee. Pain 2012;153:1837–46.
   PubMed Web of Science ®Google Scholar
• Vernalis P. Vernalis plc Completes Investment in its NCE Development [press release]. 2015. Retrieved from http://www.vernalis.com/media-centre/latest-releases/708-vernalis-plc-completes-investment-in-its-nce-development-pipeline (URL checked 28 May 2018).
   Google Scholar
• Fowler CJ. The potential of inhibitors of endocannabinoid metabolism as anxiolytic and antidepressive drugs-A practical view. Eur Neuropsychopharmacol 2015;25:749–62.
   PubMed Web of Science ®Google Scholar
• Patel S, Hill MN, Cheer JF, et al. The endocannabinoid system as a target for novel anxiolytic drugs. Neurosci Biobehav Rev 2017;76:56–66.
   PubMed Web of Science ®Google Scholar
• Storr M, Keenan C, Emmerdinger D, et al. Targeting endocannabinoid degradation protects against experimental colitis in mice: involvement of CB1 and CB2 receptors. J Mol Med 2008;86:925–36.
   PubMed Web of Science ®Google Scholar
• Sałaga M, Mokrowiecka A, Zakrzewski PK, et al. Experimental colitis in mice is attenuated by changes in the levels of endocannabinoid metabolites induced by selective inhibition of fatty acid amide hydrolase (FAAH). J Crohns Colitis 2014;8:998–1009.
   PubMed Web of Science ®Google Scholar
• Fowler CJ, Tiger G, Stenström A. Ibuprofen inhibits rat brain deamidation of anandamide at pharmacologically relevant concentrations. Mode of inhibition and structure-activity relationship. J Pharmacol Exp Ther 1997;283:729–34.
   PubMed Web of Science ®Google Scholar
• Fowler CJ, Janson U, Johnson RM, et al. Inhibition of anandamide hydrolysis by the enantiomers of ibuprofen, ketorolac, and flurbiprofen. Arch Biochem Biophys 1999;362:191–6.
   PubMed Web of Science ®Google Scholar
• Favia AD, Habrant D, Scarpelli R, et al. Identification and characterization of carprofen as a multitarget fatty acid amide hydrolase/cyclooxygenase inhibitor. J Med Chem 2012;55:8807–26.
   PubMed Web of Science ®Google Scholar
• Holt S, Paylor B, Boldrup L, et al. Inhibition of fatty acid amide hydrolase, a key endocannabinoid metabolizing enzyme, by analogues of ibuprofen and indomethacin. Eur J Pharmacol 2007;565:26–36.
   PubMed Web of Science ®Google Scholar
• Karlsson J, Morgillo CM, Deplano A, et al. Interaction of the N-(3-Methylpyridin-2-yl)amide derivatives of flurbiprofen and ibuprofen with FAAH: enantiomeric selectivity and binding mode. PLoS One 2015;10:e0142711.
   PubMed Web of Science ®Google Scholar
• Cocco M, Congiu C, Onnis V, et al. Synthesis of ibuprofen heterocyclic amides and investigation of their analgesic and toxicological properties. Eur J Med Chem 2003;38:513–18.
   PubMed Web of Science ®Google Scholar
• Fowler CJ, Björklund E, Lichtman AH, et al. Inhibitory properties of ibuprofen and its amide analogues towards the hydrolysis and cyclooxygenation of the endocannabinoid anandamide. J Enzyme Inhib Med Chem 2013;28:172–82.
   PubMed Web of Science ®Google Scholar
• Deplano A, Morgillo CM, Demurtas M, et al. Novel propanamides as fatty acid amide hydrolase inhibitors. Eur J Med Chem 2017;136:523–42.
   PubMed Web of Science ®Google Scholar
• Gustin DJ, Ma Z, Min X, et al. Identification of potent, noncovalent fatty acid amide hydrolase (FAAH) inhibitors. Bioorg Med Chem Lett 2011;21:2492–6.
   PubMed Web of Science ®Google Scholar
• Sastry GM, Adzhigirey M, Day T, et al. Protein and ligand preparation: parameters, protocols, and influence on virtual screening enrichments. J Comput Aid Mol Des 2013;27:221–34.
   PubMed Web of Science ®Google Scholar
• Schrödinger Release 2017-1: Maestro, Schrödinger, LLC, New York, NY, 2017.
   Google Scholar
• Lodola A, Castelli R, Mor M, Rivara S. Fatty acid amide hydrolase inhibitors: a patent review (2009–2014). Expert Opin Ther Pat 2015;25:1247–66.
   PubMed Web of Science ®Google Scholar
• Shelley JC, Cholleti A, Frye L, et al. Epik: a software program for pK(a) prediction and protonation state generation for drug-like molecules. J Comput Aided Mol Des 2007;21:681–91.
   PubMed Web of Science ®Google Scholar
• Sherman W, Day T, Jacobson MP, et al. Novel procedure for modeling ligand/receptor induced fit effects. J Med Chem 2006;49:534–53.
   PubMed Web of Science ®Google Scholar
• Schrödinger Suite 2017-1 Induced Fit Docking protocol; Glide, Schrödinger, LLC, New York, NY, 2017; Prime, Schrödinger, LLC, New York, NY, 2017.
   Google Scholar
• Boldrup L, Wilson SJ, Barbier AJ, Fowler CJ. A simple stopped assay for fatty acid amide hydrolase avoiding the use of a chloroform extraction phase. J Biochem Biophys Methods 2004;60:171–7.
   PubMedGoogle Scholar
• Wilson AA, Hicks JW, Sadovski O, et al. Carbonyl‐labeled carbamates as fatty acid amide hydrolase radiotracers for positron emission tomography. J Med Chem 2013;56:201–9.
   PubMed Web of Science ®Google Scholar