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N-arachidonoylethanolamine + H2O
arachidonic acid + ethanolamine
-
-
-
?
2-arachidonoylglycerol + H2O
?
-
FAAH is responsible for approximately one-half of the 2-arachidonoylglycerol hydrolysis occurring in BV-2 cell homogenate
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
anandamide + H2O
ethanolamine + arachidonic acid
N-(2-hydroxyethyl)linoleoylamide + H2O
?
-
-
-
-
?
oleamide + H2O
oleic acid + NH3
anandamide + H2O
arachidonic acid + ethanolamine
-
-
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. N-arachidonoylethanolamine
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
-
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
anandamide hydrolysis in BV-2 cells is entirely attributable to FAAH
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
fatty acid amide hydrolase is a modulator of endogenous signaling compounds affecting sleep (oleamide) and analgesia (anandamide)
-
-
?
oleamide + H2O
oleic acid + NH3
-
-
-
-
?
oleamide + H2O
oleic acid + NH3
-
fatty acid amide hydrolase is a modulator of endogenous signaling compounds affecting sleep (oleamide) and analgesia (anandamide)
-
-
?
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2-arachidonoylglycerol + H2O
?
-
FAAH is responsible for approximately one-half of the 2-arachidonoylglycerol hydrolysis occurring in BV-2 cell homogenate
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
anandamide + H2O
ethanolamine + arachidonic acid
oleamide + H2O
oleic acid + NH3
-
fatty acid amide hydrolase is a modulator of endogenous signaling compounds affecting sleep (oleamide) and analgesia (anandamide)
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
-
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. N-arachidonoylethanolamine
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
anandamide hydrolysis in BV-2 cells is entirely attributable to FAAH
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
fatty acid amide hydrolase is a modulator of endogenous signaling compounds affecting sleep (oleamide) and analgesia (anandamide)
-
-
?
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PF-04457845
potently inhibits the enzyme regardless the route selected
URB597
less effective inhibitor in the brain after oral administration while it reaches similar effects by intranasal (i.n.) and intraperitoneal routes. Intranasal URB597 delivery always increased N-acyl-ethanolamine levels in brain areas, whereas a parallel increase is not observed in the liver. By showing the efficacy of intranasal FAAH inhibition, evidence is provided that nose-to-brain delivery is a suitable alternative to enhance brain endocannabinoid tone for the treatment of neurodegenerative disorders and improve compliance of the patients
(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
-
i.e. (5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide or N-arachidonoylethanolamine, competitive
1,1-biphenyl-3-yl-carbamic acid cyclohexyl ester
-
i.e. URB602
2-iodobenzylarachidonoylamide
-
-
2-iodobenzyllinoleoylamide
-
-
2-iodophenethylarachidonoylamide
-
-
2-iodophenethyllinoleoylamide
-
-
2-methoxyphenethylarachidonoylamide
-
-
2-methoxyphenethyllinoleoylamide
-
-
3-iodobenzylarachidonoylamide
-
-
3-iodobenzyllinoleoylamide
-
-
3-iodophenethylarachidonoylamide
-
-
3-iodophenethyllinoleoylamide
-
-
3-methoxyphenethylarachidonoylamide
-
-
3-methoxyphenethyllinoleoylamide
-
-
4-iodobenzylarachidonoylamide
-
-
4-iodobenzyllinoleoylamide
-
-
4-iodophenethylarachidonoylamide
-
-
4-iodophenethyllinoleoylamide
-
-
4-methoxyphenethylarachidonoylamide
-
-
4-methoxyphenethyllinoleoylamide
-
-
cyclohexylcarbamic acid 3'-carbamoylbiphenyl-3-yl ester
-
i.e. URB597, attenuates the development of lipopolysaccharide-induced paw edema and reverses lipopolysaccharide-induced hyperalgesia through the respective CB2 and CB1 mechanisms of action. The inhibition is not affected by capsazepine, a transient receptor potential vanilloid type 1 antagonist
decyl benzodioxaphosphorin oxide
-
-
diisopropyl fluorophosphate
-
-
dodecyl benzodioxaphosphorin oxide
-
-
dodecyl sulfonyl fluoride
-
-
dodecyl-benzodioxaphosphorin oxide
-
-
ethyl octylphosphonofluoridate
-
-
heptyl benzodioxaphosphorin oxide
-
-
isopropyl dodecylfluorophosphate
-
-
methyl arachidonyl fluorophosphonate
methyl arachidonyl phosphonofluoridate
-
-
methyl arachidonylfluoroposphate
-
-
methyl octylphosphonofluoridate
-
-
N-(2-hydroxyethyl)linoleoylamide
-
competitive versus anadamide
N-n-heptyl benzodioxaphosphorin oxide
-
-
O-n-octyl benzodioxaphosphorin oxide
-
-
O-octyl-benzodioxaphosphorin oxide
-
-
octyl sulfonyl fluoride
-
-
octyl-benzodioxaphosphorin oxide
-
-
oleoyl ethylamide
-
FAAH inhibitor
oleyl-benzodioxaphosphorin oxide
-
-
palmitoyl ethanolamide
-
a non-CB1 non-CB2 cannabinoid-like compound
PF-3845
-
FAAH inhibitor, in vivo inhibition
phenyl-benzodioxaphosphorin oxide
-
-
S-heptyl benzodioxaphosphorin oxide
-
-
S-nonyl benzodioxaphosphorin oxide
-
-
S-pentyl benzodioxaphosphorin oxide
-
-
stearyl benzodioxaphosphorin oxide
-
-
methyl arachidonyl fluorophosphonate
-
-
methyl arachidonyl fluorophosphonate
-
MAFP, a potent irreversible FAAH inhibitor
additional information
-
the microglial-specific isozyme is not inhibited by URB597, i.e. 3'-carbamoyl-biphenyl-3-ylcyclohexylcarbamate, and inhibitors of cyclooxygenases, lipooxygenases, and diacylglycerol lipases, overview
-
additional information
-
organophosphorus compound-induced FAAH inhibition and the associated anandamide accumulation may lead to reduced limb mobility as a secondary neurotoxic effect
-
additional information
-
synthesis of 18 aryl analogues of anandamide. In vitro evaluation of inhibitory potency, binding to CB1 and CB2 cannabinoid receptors, and potential as metabolic trapping tracers of 4-methoxyphenethyllinoleoylamide and 4-methoxyphenethylarachidonoylamide, overview
-
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0.011
benzol
Mus musculus
-
-
0.00004 - 0.000056
chlorpyrifos oxon
0.0000012
decyl benzodioxaphosphorin oxide
Mus musculus
-
-
0.009
diazoxon
Mus musculus
-
-
0.0018
dichlorvos
Mus musculus
-
-
0.048
diisopropyl fluorophosphate
Mus musculus
-
-
0.0000005
dodecyl benzodioxaphosphorin oxide
Mus musculus
-
-
0.000002
dodecyl sulfonyl fluoride
Mus musculus
-
-
0.0000009 - 0.000005
dodecyl-benzodioxaphosphorin oxide
0.0000006 - 0.0000011
ethyl octylphosphonofluoridate
0.000126
heptyl benzodioxaphosphorin oxide
Mus musculus
-
-
0.000002
isopropyl dodecylfluorophosphate
Mus musculus
-
-
0.0000001 - 0.000082
methyl arachidonyl phosphonofluoridate
0.0000001
methyl arachidonylfluoroposphate
Mus musculus
-
-
0.00000079
methyl octylphosphonofluoridate
Mus musculus
-
-
0.000064
N-n-heptyl benzodioxaphosphorin oxide
Mus musculus
-
-
0.000073
O-n-octyl benzodioxaphosphorin oxide
Mus musculus
-
-
0.000024 - 0.000073
O-octyl-benzodioxaphosphorin oxide
0.000019
octyl sulfonyl fluoride
Mus musculus
-
-
0.000007 - 0.0000081
octyl-benzodioxaphosphorin oxide
0.00000018 - 0.00000067
oleyl-benzodioxaphosphorin oxide
0.00054 - 0.00077
paraoxon
0.0089 - 0.011
phenyl-benzodioxaphosphorin oxide
0.00015 - 0.00027
profenofos
0.0000017
S-heptyl benzodioxaphosphorin oxide
Mus musculus
-
-
0.00000015
S-nonyl benzodioxaphosphorin oxide
Mus musculus
-
-
0.0000057
S-pentyl benzodioxaphosphorin oxide
Mus musculus
-
-
0.000131
stearyl benzodioxaphosphorin oxide
Mus musculus
-
-
additional information
additional information
Mus musculus
-
pIC50, i.e. -log IC50. values of anadamide analogue inhibitors, overview
-
0.00004
chlorpyrifos oxon
Mus musculus
-
-
0.00004
chlorpyrifos oxon
Mus musculus
-
25°C, pH 9.0, brain enzyme
0.000056
chlorpyrifos oxon
Mus musculus
-
25°C, pH 9.0, liver enzyme
0.029
DFP
Mus musculus
-
25°C, pH 9.0, liver enzyme
0.048
DFP
Mus musculus
-
25°C, pH 9.0, brain enzyme
0.0000009
dodecyl-benzodioxaphosphorin oxide
Mus musculus
-
25°C, pH 9.0, liver enzyme
0.000005
dodecyl-benzodioxaphosphorin oxide
Mus musculus
-
25°C, pH 9.0, brain enzyme
0.0000006
ethyl octylphosphonofluoridate
Mus musculus
-
-
0.0000006
ethyl octylphosphonofluoridate
Mus musculus
-
25°C, pH 9.0, brain enzyme
0.0000011
ethyl octylphosphonofluoridate
Mus musculus
-
25°C, pH 9.0, liver enzyme
0.0000001
methyl arachidonyl phosphonofluoridate
Mus musculus
-
25°C, pH 9.0, brain enzyme
0.000082
methyl arachidonyl phosphonofluoridate
Mus musculus
-
25°C, pH 9.0, liver enzyme
0.000024
O-octyl-benzodioxaphosphorin oxide
Mus musculus
-
25°C, pH 9.0, liver enzyme
0.000073
O-octyl-benzodioxaphosphorin oxide
Mus musculus
-
25°C, pH 9.0, brain enzyme
0.000007
octyl-benzodioxaphosphorin oxide
Mus musculus
-
25°C, pH 9.0, liver enzyme
0.0000081
octyl-benzodioxaphosphorin oxide
Mus musculus
-
25°C, pH 9.0, brain enzyme
0.00000018
oleyl-benzodioxaphosphorin oxide
Mus musculus
-
25°C, pH 9.0, liver enzyme
0.00000067
oleyl-benzodioxaphosphorin oxide
Mus musculus
-
25°C, pH 9.0, brain enzyme
0.00054
paraoxon
Mus musculus
-
-
0.00054
paraoxon
Mus musculus
-
25°C, pH 9.0, brain enzyme
0.00077
paraoxon
Mus musculus
-
25°C, pH 9.0, liver enzyme
0.0089
phenyl-benzodioxaphosphorin oxide
Mus musculus
-
25°C, pH 9.0, liver enzyme
0.011
phenyl-benzodioxaphosphorin oxide
Mus musculus
-
25°C, pH 9.0, brain enzyme
0.00015
profenofos
Mus musculus
-
25°C, pH 9.0, liver enzyme
0.00027
profenofos
Mus musculus
-
25°C, pH 9.0, brain enzyme
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metabolism
-
fatty acid amide hydrolase is a key regulator of endocannabinoid-induced myocardial tissue injury
additional information
-
anandamide induces enhanced cell death in human cardiomyocytes pretreated by FAAH inhibitor, and enhances sensitivity to reactive oxygen species generation in inflammatory cells of FAAH knockouts, it triggers concentration-dependent respiratory burst (ROS generation) in neutrophil granulocytes isolated from FAAH+/+ mice
malfunction
-
genetic deletion of FAAH is associated with enhanced acute doxorubicin-induced myocardial cell death and decreased survival, mechanism of the doxorubicin-induced myocardial cell death in FAAH+/+ and FAAH-/- mice, overview
malfunction
-
tissue-specific changes in N-acyl ethanolamine congeners and N-acyl taurines metabolism caused by FAAH disruption in central and peripheral tissues, overview
physiological function
-
FAAH is the chief catabolic enzyme regulating the endogenous cannabinoid N-arachidonoylethanolamine, i.e. anandamide
physiological function
-
genetic or pharmacological ablation of FAAH promotes analgesia and anxiolytic effects without disrupting motor coordination
physiological function
-
importance of FAAH in controlling endogenous anandamide levels in the brain and consequently the importance of FAAH as a regulatory enzyme for key physiological functions. FAAH is one of the main enzymes responsible for terminating the signaling of endocannabinoids in the brain, it has a role in neuropsychiatric disorders
physiological function
-
endocannabinoid-degrading enzyme fatty acid amide hydrolase. FAAH substrates in the urinary bladder act via local CB2-mediated signals
physiological function
-
fatty acid amide hydrolase is a key regulator of endocannabinoid-induced myocardial tissue injury
physiological function
-
fatty acid amide hydrolase is the principal enzyme responsible for anandamide hydrolysis in mammalian tissues and regulates amidated lipid transmitters, including the endocannabinoid anandamide and its N-acyl ethanolamine congeners and transient receptor potential channel agonists N-acyl taurines, in a tissue-specific manner, overview
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Quistad, G.B.; Klintenberg, R.; Caboni, P.; Liang, S.N.; Casida, J.E.
Monoacylglycerol lipase inhibition by organophosphorus compounds leads to elevation of brain 2-arachidonoylglycerol and the associated hypomotility in mice
Toxicol. Appl. Pharmacol.
211
78-83
2006
Mus musculus
brenda
Muccioli, G.G.; Xu, C.; Odah, E.; Cudaback, E.; Cisneros, J.A.; Lambert, D.M.; Lopez Rodriguez, M.L.; Bajjalieh, S.; Stella, N.
Identification of a novel endocannabinoid-hydrolyzing enzyme expressed by microglial cells
J. Neurosci.
27
2883-2889
2007
Mus musculus
brenda
Wei, B.Q.; Mikkelsen, T.S.; McKinney, M.K.; Lander, E.S.; Cravatt, B.F.
A second fatty acid amide hydrolase with variable distribution among placental mammals
J. Biol. Chem.
281
36569-36578
2006
Homo sapiens (O00519), Homo sapiens (Q6GMR7), Homo sapiens, Mus musculus (O08914), Mus musculus, Rattus norvegicus (P97612)
brenda
Fowler, C.J.; Jonsson, K.O.; Tiger, G.
Fatty acid amide hydrolase: biochemistry, pharmacology, and therapeutic possibilities for an enzyme hydrolyzing anandamide, 2-arachidonoylglycerol, palmitoylethanolamide, and oleamide
Biochem. Pharmacol.
62
517-26
2001
Homo sapiens, Mus musculus, Rattus norvegicus, Sus scrofa
brenda
Giang, D.K.; Cravatt, B.F.
Molecular characterization of human and mouse fatty acid amide hydrolases
Proc. Natl. Acad. Sci. USA
94
2238-2242
1997
Rattus norvegicus, Homo sapiens (O00519), Homo sapiens, Mus musculus (O08914), Mus musculus
brenda
Quistad, G.B.; Sparks, S.E.; Casida, J.E.
Fatty acid amide hydrolase inhibition by neurotoxic organophosphorus pesticides
Toxicol. Appl. Pharmacol.
173
48-55
2001
Mus musculus
brenda
Wyffels, L.; Muccioli, G.G.; De Bruyne, S.; Moerman, L.; Sambre, J.; Lambert, D.M.; De Vos, F.
Synthesis, in vitro and in vivo evaluation, and radiolabeling of aryl anandamide analogues as candidate radioligands for in vivo imaging of fatty acid amide hydrolase in the brain
J. Med. Chem.
52
4613-4622
2009
Mus musculus
brenda
Naidu, P.S.; Kinsey, S.G.; Guo, T.L.; Cravatt, B.F.; Lichtman, A.H.
Regulation of inflammatory pain by inhibition of fatty acid amide hydrolase
J. Pharmacol. Exp. Ther.
334
182-190
2010
Mus musculus
brenda
Glaser, S.T.; Kaczocha, M.
Temporal changes in mouse brain fatty acid amide hydrolase activity
Neuroscience
163
594-600
2009
Mus musculus
brenda
Strittmatter, F.; Gandaglia, G.; Benigni, F.; Bettiga, A.; Rigatti, P.; Montorsi, F.; Gratzke, C.; Stief, C.; Colciago, G.; Hedlund, P.
Expression of fatty acid amide hydrolase (FAAH) in human, mouse, and rat urinary bladder and effects of FAAH inhibition on bladder function in awake rats
Eur. Urol.
61
98-106
2012
Homo sapiens, Mus musculus, Rattus norvegicus, Rattus norvegicus Sprague-Dawley
brenda
Mukhopadhyay, P.; Horvath, B.; Rajesh, M.; Matsumoto, S.; Saito, K.; Batkai, S.; Patel, V.; Tanchian, G.; Gao, R.Y.; Cravatt, B.F.; Hasko, G.; Pacher, P.
Fatty acid amide hydrolase is a key regulator of endocannabinoid-induced myocardial tissue injury
Free Radic. Biol. Med.
50
179-195
2011
Homo sapiens, Mus musculus, Mus musculus C57/BL6J
brenda
Long, J.Z.; LaCava, M.; Jin, X.; Cravatt, B.F.
An anatomical and temporal portrait of physiological substrates for fatty acid amide hydrolase
J. Lipid Res.
52
337-344
2011
Mus musculus
brenda
Giacovazzo, G.; Bisogno, T.; Piscitelli, F.; Verde, R.; Oddi, S.; Maccarrone, M.; Coccurello, R.
Different routes to inhibit fatty acid amide hydrolase do all roads lead to the same place?
Int. J. Mol. Sci.
20
E4503
2019
Mus musculus (O08914)
brenda