Literature DB >> 24900385

Aryl Piperazinyl Ureas as Inhibitors of Fatty Acid Amide Hydrolase (FAAH) in Rat, Dog, and Primate.

John M Keith1, Rich Apodaca1, Mark Tichenor1, Wei Xiao1, William Jones1, Joan Pierce1, Mark Seierstad1, James Palmer1, Michael Webb1, Mark Karbarz1, Brian Scott1, Sandy Wilson1, Lin Luo1, Michelle Wennerholm1, Leon Chang1, Sean Brown1, Michele Rizzolio1, Raymond Rynberg1, Sandra Chaplan1, J Guy Breitenbucher1.   

Abstract

A series of aryl piperazinyl ureas that act as covalent inhibitors of fatty acid amide hydrolase (FAAH) is described. A potent and selective (does not inhibit FAAH-2) member of this class, JNJ-40355003, was found to elevate the plasma levels of three fatty acid amides: anandamide, oleoyl ethanolamide, and palmitoyl ethanolamide, in the rat, dog, and cynomolgous monkey. The elevation of the levels of these lipids in the plasma of monkeys suggests that FAAH-2 may not play a significant role in regulating plasma levels of fatty acid ethanolamides in primates.

Entities:  

Keywords:  FAAH; FAAH-2; anandamide; enzyme; ethanolamides; urea

Year:  2012        PMID： 24900385      PMCID： PMC4025847          DOI： 10.1021/ml300186g

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  38 in total

1.  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.

Authors:  John P Huggins; Trevor S Smart; Stephen Langman; Louise Taylor; Tim Young
Journal:  Pain       Date:  2012-06-21       Impact factor: 6.961

2.  QSAR models for discriminating between mutagenic and nonmutagenic aromatic and heteroaromatic amines.

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3.  Supersensitivity to anandamide and enhanced endogenous cannabinoid signaling in mice lacking fatty acid amide hydrolase.

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Journal:  Proc Natl Acad Sci U S A       Date:  2001-07-24       Impact factor: 11.205

4.  Fatty acid amide hydrolase competitively degrades bioactive amides and esters through a nonconventional catalytic mechanism.

Authors:  M P Patricelli; B F Cravatt
Journal:  Biochemistry       Date:  1999-10-26       Impact factor: 3.162

5.  Discovery of PF-04457845: A Highly Potent, Orally Bioavailable, and Selective Urea FAAH Inhibitor.

Authors:  Douglas S Johnson; Cory Stiff; Scott E Lazerwith; Suzanne R Kesten; Lorraine K Fay; Mark Morris; David Beidler; Marya B Liimatta; Sarah E Smith; David T Dudley; Nalini Sadagopan; Shobha N Bhattachar; Stephen J Kesten; Tyzoon K Nomanbhoy; Benjamin F Cravatt; Kay Ahn
Journal:  ACS Med Chem Lett       Date:  2011-02-10       Impact factor: 4.345

Review 6.  Oleamide: an endogenous sleep-inducing lipid and prototypical member of a new class of biological signaling molecules.

Authors:  D L Boger; S J Henriksen; B F Cravatt
Journal:  Curr Pharm Des       Date:  1998-08       Impact factor: 3.116

7.  Mechanistic and pharmacological characterization of PF-04457845: a highly potent and selective fatty acid amide hydrolase inhibitor that reduces inflammatory and noninflammatory pain.

Authors:  Kay Ahn; Sarah E Smith; Marya B Liimatta; David Beidler; Nalini Sadagopan; David T Dudley; Tim Young; Paul Wren; Yanhua Zhang; Steven Swaney; Keri Van Becelaere; Jacqueline L Blankman; Daniel K Nomura; Shobha N Bhattachar; Cory Stiff; Tyzoon K Nomanbhoy; Eranthie Weerapana; Douglas S Johnson; Benjamin F Cravatt
Journal:  J Pharmacol Exp Ther       Date:  2011-04-19       Impact factor: 4.030

8.  Fatty acid amide hydrolase substrate specificity.

Authors:  D L Boger; R A Fecik; J E Patterson; H Miyauchi; M P Patricelli; B F Cravatt
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Review 9.  The palmitoylethanolamide family: a new class of anti-inflammatory agents?

Authors:  Didier M Lambert; Severine Vandevoorde; Kent-Olov Jonsson; Christopher J Fowler
Journal:  Curr Med Chem       Date:  2002-03       Impact factor: 4.530

10.  Molecular characterization of a peripheral receptor for cannabinoids.

Authors:  S Munro; K L Thomas; M Abu-Shaar
Journal:  Nature       Date:  1993-09-02       Impact factor: 49.962
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Journal:  J Med Chem       Date:  2020-05-08       Impact factor: 7.446

2.  Stress-induced modulation of endocannabinoid signaling leads to delayed strengthening of synaptic connectivity in the amygdala.

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Journal:  Proc Natl Acad Sci U S A       Date:  2019-12-16       Impact factor: 11.205

3.  Preclinical Characterization of the FAAH Inhibitor JNJ-42165279.

Authors:  John M Keith; William M Jones; Mark Tichenor; Jing Liu; Mark Seierstad; James A Palmer; Michael Webb; Mark Karbarz; Brian P Scott; Sandy J Wilson; Lin Luo; Michelle L Wennerholm; Leon Chang; Michele Rizzolio; Raymond Rynberg; Sandra R Chaplan; J Guy Breitenbucher
Journal:  ACS Med Chem Lett       Date:  2015-11-02       Impact factor: 4.345

4.  Lowering Lipophilicity by Adding Carbon: AzaSpiroHeptanes, a logD Lowering Twist.

Authors:  Sébastien L Degorce; Michael S Bodnarchuk; James S Scott
Journal:  ACS Med Chem Lett       Date:  2019-07-18       Impact factor: 4.345

5.  Rational design of fatty acid amide hydrolase inhibitors that act by covalently bonding to two active site residues.

Authors:  Katerina Otrubova; Monica Brown; Michael S McCormick; Gye W Han; Scott T O'Neal; Benjamin F Cravatt; Raymond C Stevens; Aron H Lichtman; Dale L Boger
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7.  Discovery libraries targeting the major enzyme classes: the serine hydrolases.

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8.  α-Ketoheterocycle inhibitors of fatty acid amide hydrolase: exploration of conformational constraints in the acyl side chain.

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9.  Design, synthesis, and characterization of α-ketoheterocycles that additionally target the cytosolic port Cys269 of fatty acid amide hydrolase.

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Review 10.  Inhibitors of Fatty Acid Amide Hydrolase and Monoacylglycerol Lipase: New Targets for Future Antidepressants.

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