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Information on EC 3.5.1.99 - fatty acid amide hydrolase
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3.5.1.99 fatty acid amide hydrolaseIUBMB Comments
Integral membrane protein, the enzyme is responsible for the catabolism of neuromodulatory fatty acid amides, including anandamide and oleamide, occurs in mammalia.
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Word Map
- 3.5.1.99
-
endocannabinoids
- cannabinoids
- agonist
- pain
- lipase
- 2-arachidonoylglycerol
- monoacylglycerol
- cannabis
-
vanilloid
- n-acylethanolamines
-
analgesic
-
anxiety
- nape-pld
-
tone
- n-arachidonoylethanolamine
- amygdala
-
emotional
- marijuana
- delta9-tetrahydrocannabinol
- amidase
- ethanolamide
-
anxiolytic
-
2-arachidonoyl
-
neuropathic
-
antinociceptive
-
rimonabant
-
nociceptive
- carbamate
- palmitoylethanolamide
- oleoylethanolamide
- hyperalgesia
-
cannabimimetic
- medicine
-
periaqueductal
- pharmacology
-
anti-allodynic
-
dagls
-
psychoactive
-
monoacyl
- monoglyceride
-
neuromodulatory
- fluorophosphonate
- tetrahydrocannabinol
- cannabidiol
-
capsazepine
- drug development
-
anxiety-like
-
sleep-inducing
-
anxiolytic-like
-
arachidonyl
-
anti-hyperalgesic
- catalepsy
-
phytocannabinoids
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
+
=
+
Synonyms
AAH, anandamide amidohydrolase, AtFAAH, endocannabinoid-degrading enzyme, FA amide hydrolase, FAAH, FAAH-1, FAAH-2, fatty acid amide hydrolase, fatty-acid amide hydrolase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
FAAH
FAAH-1
FAAH-2
fatty acid amide hydrolase
FAAH
-
-
FAAH
-
-
FAAH
-
-
FAAH
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
anandamide + H2O = arachidonic acid + ethanolamine
-
-
-
-
anandamide + H2O = arachidonic acid + ethanolamine
structure-function relationship and catalytic mechanism, overview
oleamide + H2O = oleic acid + NH3
-
-
-
-
oleamide + H2O = oleic acid + NH3
structure-function relationship and catalytic mechanism, overview
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PATHWAY SOURCE
PATHWAYS
MetaCyc
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SYSTEMATIC NAME
IUBMB Comments
fatty acylamide amidohydrolase
Integral membrane protein, the enzyme is responsible for the catabolism of neuromodulatory fatty acid amides, including anandamide and oleamide, occurs in mammalia.
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CAS REGISTRY NUMBER
COMMENTARY
153301-19-0
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(11Z)-eicosenamide + H2O
(11Z)-eicosenoic acid + NH3
-
105% of the activity with oleamide
-
-
?
(12Z)-octadecenamide + H2O
(12Z)-octadecenoic acid + NH3
-
92% of the activity with oleamide
-
-
?
(13Z)-eicosenamide + H2O
(13Z)-eicosenoic acid + NH3
-
103% of the activity with oleamide
-
-
?
(13Z)-octadecenamide + H2O
(13Z)-octadecenoic acid + NH3
-
82% of the activity with oleamide
-
-
?
(15Z)-octadecenamide + H2O
(15Z)-octadecenoic acid + NH3
-
90% of the activity with oleamide
-
-
?
(5Z)-eicosenamide + H2O
(5Z)-eicosenoic acid + NH3
-
116% of the activity with oleamide
-
-
?
(5Z,8Z,11Z,14Z)-N-(2-fluoroethyl)icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolysis rate is 1.3fold higher than the rate of anandamide hydrolysis
-
-
?
(5Z,8Z,11Z,14Z)-N-(2-hydroxy-1,1-dimethylethyl)icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolyzed at 4.3% the rate of anandamide
-
-
?
(5Z,8Z,11Z,14Z)-N-(2-methylpropyl)icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolyzed at 2% the rate of anandamide
-
-
?
(5Z,8Z,11Z,14Z)-N-(3-hydroxyphenyl)icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolysis rate is 1.5fold higher than the rate of anandamide hydrolysis
-
-
?
(5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolyzed at 16% the rate of anandamide
-
-
?
(5Z,8Z,11Z,14Z)-N-tert-butylicosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolyzed at 1.8% the rate of anandamide
-
-
?
(5Z,8Z,11Z,14Z)-N-[(1S)-1-methylpropyl]icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolyzed at 6.3% the rate of anandamide
-
-
?
(5Z,8Z,11Z,14Z)-N-[(2R)-2-hydroxypropyl]icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolysis rate is 1.2fold higher than the rate of anandamide hydrolysis
-
-
?
(5Z,8Z,11Z,14Z)-N-[(2S)-2-hydroxypropyl]icosa-5,8,11,14-tetraenamide + H2O
?
-
hydrolyzed at 21% the rate of anandamide
-
-
?
(6Z)-octadecenamide + H2O
(6Z)-octadecenoic acid + NH3
-
91% of the activity with oleamide
-
-
?
(7Z)-octadecenamide + H2O
(7Z)-octadecenoic acid + NH3
-
109% of the activity with oleamide
-
-
?
(8Z)-eicosenamide + H2O
(8Z)-eicosenoic acid + NH3
-
112% of the activity with oleamide
-
-
?
(9E)-octadecenamide + H2O
(9E)-octadecenoic acid + NH3
-
52% of the activity with oleamide
-
-
?
(9Z)-N-(2-hydroxyethyl)octadec-9-enamide + H2O
?
-
hydrolyzed at 61% the rate of anandamide
-
-
?
(9Z)-tetradec-9-enamide + H2O
myristoleic acid + NH3
-
86% of the activity with oleamide
-
-
?
(9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamide + H2O
?
-
hydrolyzed at 75% the rate of anandamide
-
-
?
(9Z,12Z)-N-[(1R)-2-hydroxy-1-methylethyl]octadeca-9,12-dienamide + H2O
?
-
hydrolyzed at 20.5% the rate of anandamide
-
-
?
(9Z,12Z)-octadeca-9,12-dienamide + H2O
(9Z,12Z)-octadeca-9,12-dienoate + NH3
-
104% of the activity with oleamide
-
-
?
(R)-alpha-methanandamide + H2O
?
-
2.4% of the activity with anandamide
-
-
?
(R)-beta-methanandamide + H2O
?
-
121% of the activity with anandamide
-
-
?
(S)-alpha-methanandamide + H2O
?
-
23% of the activity with anandamide
-
-
?
(S)-beta-methanandamide + H2O
?
-
21% of the activity with anandamide
-
-
?
11,14,17-eicosatrienamide + H2O
11,14,17-eicosatrienoic acid + NH3
-
140% of the activity with oleamide
-
-
?
11,14-eicosadienamide + H2O
? + NH3
-
127% of the activity with oleamide
-
-
?
2,2-dimethyloleamide + H2O
2,2-dimethyloleic acid + NH3
-
3% of the activity with oleamide
-
-
?
2-methyloleamide + H2O
2-methyloleic acid + NH3
-
7% of the activity with oleamide
-
-
?
8,11,14-eicosatrienamide + H2O
8,11,14-eicosatrienoic acid + NH3
-
138% of the activity with oleamide
-
-
?
all-trans-anandamide + H2O
ethanolamine + arachidonic acid
-
all-trans-anandamide is an equally good substrate for rabbit platelet FAAH compared to anandamide
-
-
?
alpha-linolenamide + H2O
? + NH3
-
138% of the activity with oleamide
-
-
?
arachidonyl-7-amino-4-methylcoumarin amide + H2O
arachidonic acid + 7-amino-4-methylcoumarin
beta-arachidonoylglycerol + H2O
?
-
hydrolysis is 2.5fold higher than the rate of anandamide hydrolysis
-
-
?
dodecanoamide + H2O
dodecanoic acid + NH3
-
74% of the activity with oleamide
-
-
?
linoelaidamide + H2O
(9E,12E)-octadeca-9,12-dienoic acid + NH3
-
54% of the activity with oleamide
-
-
?
N-(2-hydroxyethyl)-4-pyren-1-ylbutanamide + H2O
4-(pyren-1-yl)butanamide + ethylene glycol
-
-
-
?
N-(2-hydroxyethyl)-4-pyren-1-ylbutanamide + H2O
4-pyren-1-ylbutanoic acid + ?
-
-
-
-
?
N-(2-hydroxyethyl)octadecanamide + H2O
?
-
hydrolyzed at 15.0% the rate of anandamide
-
-
?
N-(4-hydroxy-2-methylphenyl) arachidonoyl amide + H2O
4-amino-m-cresol + NH3
-
the rate of metabolism of VDM11 is about 15–20% of that for anandamide
-
-
?
N-oleoyltaurine + H2O
taurine + oleic acid
4% of the activity with anandamide
-
-
?
palmitoamide + H2O
palmitic acid + NH3
-
72% of the activity with oleamide
-
-
?
palmitoleamide + H2O
palmitoleic acid + NH3
-
79% of the activity with oleamide
-
-
?
palmitoylethanolamide + H2O
palmitic acid + ethanolamine
-
substrate of FAAH and FAAH-2, the latter shows lower activity than FAAH
-
-
?
stearamide + H2O
stearic acid + NH3
-
69% of the activity with oleamide
-
-
?
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
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide, LC-MS/MS analysis
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
substrate of FAAH and FAAH-2, the latter shows lower activity than FAAH
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. N-arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide, LC-MS/MS analysis
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. N-arachidonoylethanolamine
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
FAAH-1 plays a primary role in regulating endocannabinoid signaling
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
5% of the activity with oleamide
-
-
?
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)
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
the enzyme cleaves anandamide and regulates in vivo the magnitude and duration of the signaling induced by this lipid messenger
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
-
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
enzyme is responsible for the catabolism of neuromodulatory fatty acid amides, including anandamide and oleamide
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
the enzyme is responsible for the hydrolysis of a number of neuromodulatory fatty acid amides, including the endogenous cannabinoid anandamide and the sleep-inducing lipid oleamide
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
the serine hydrolase is responsible for the degradation of endogenous oleamide and anandamide, fatty acid amides that function as chemical messengers
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
168% of the activity with oleamide
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
-
-
?
arachidonamide + H2O
arachidonic acid + NH3
-
311% of the activity with oleamide
-
-
?
arachidonoyl 7-amido-4-methylcoumarin + H2O
arachidonic acid + 7-amino-4-methylcoumarin
-
-
-
-
?
arachidonoyl 7-amido-4-methylcoumarin + H2O
arachidonic acid + 7-amino-4-methylcoumarin
-
-
-
-
?
arachidonyl-7-amino-4-methylcoumarin amide + H2O
arachidonic acid + 7-amino-4-methylcoumarin
fluorogenic substrate
-
-
?
arachidonyl-7-amino-4-methylcoumarin amide + H2O
arachidonic acid + 7-amino-4-methylcoumarin
fluorogenic substrate
-
-
?
myristic amide + H2O
myristic acid + NH3
65% of the activity with anandamide
-
-
?
myristic amide + H2O
myristic acid + NH3
-
24.3% of the activity with oleamide
-
-
?
myristic amide + H2O
myristic acid + NH3
-
24% of the activity with anandamide
-
-
?
myristic amide + H2O
myristic acid + NH3
-
83% of the activity with oleamide
-
-
?
N-arachidonoylethanolamine + H2O
arachidonic acid + ethanolamine
-
-
-
?
N-arachidonoylethanolamine + H2O
arachidonic acid + ethanolamine
-
-
-
?
N-arachidonoylethanolamine + H2O
arachidonic acid + ethanolamine
-
-
-
?
N-oleoylethanolamine + H2O
oleic acid + ethanolamine
23% of the activity with oleamide
-
-
?
N-oleoylethanolamine + H2O
oleic acid + ethanolamine
33% of the activity with anandamide
-
-
?
N-palmitoylethanolamine + H2O
palmitic acid + ethanolamine
12% of the activity with anandamide
-
-
?
N-palmitoylethanolamine + H2O
palmitic acid + ethanolamine
2.3% of the activity with oleamide
-
-
?
oleamide + H2O
oleic acid + NH3
57% of the activity with anandamide
-
-
?
oleamide + H2O
oleic acid + NH3
-
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
-
enzyme is responsible for the catabolism of neuromodulatory fatty acid amides, including anandamide and oleamide
-
-
?
oleamide + H2O
oleic acid + NH3
-
role of FAAH in epithelial cells of the choroid plexus may be to control the concentration of oleamide in the cerebrospinal fluid. FAAH may exert an important regulatory role in shaping the duration and magnitude of the sleep-inducing effect of endogenously or exogenously derived oleamide
-
-
?
oleamide + H2O
oleic acid + NH3
-
the enzyme is responsible for the hydrolysis of a number of neuromodulatory fatty acid amides, including the endogenous cannabinoid anandamide and the sleep-inducing lipid oleamide
-
-
?
oleamide + H2O
oleic acid + NH3
-
the serine hydrolase is responsible for the degradation of endogenous oleamide and anandamide, fatty acid amides that function as chemical messengers
-
-
?
oleamide + H2O
oleic acid + NH3
-
serine residue 241 acts as the catalytic nucleophile of the enzyme. FAAH does not utilize a histidine base for the activation of its serine nucleophile
-
-
?
palmitic amide + H2O
palmitic acid + NH3
33% of the activity with anandamide
-
-
?
palmitic amide + H2O
palmitic acid + NH3
-
10% of the activity with anandamide
-
-
?
palmitic amide + H2O
palmitic acid + NH3
-
9.9% of the activity with oleamide
-
-
?
stearic amide + H2O
stearic acid + NH3
5.8% of the activity with anandamide
-
-
?
stearic amide + H2O
stearic acid + NH3
-
5.8% of the activity with anandamide
-
-
?
stearic amide + H2O
stearic acid + NH3
-
5.8% of the activity with oleamide
-
-
?
additional information
?
-
-
the substrate specificity of fatty acid ethanolamides decreased with decreasing length, number of double bonds, and lipophilicity of the fatty acid skeleton
-
-
?
additional information
?
-
-
FAAH inactivates anandamide and other bioactive N-acylethanolamines
-
-
?
additional information
?
-
-
the substrate specificity of fatty acid ethanolamides decreased with decreasing length, number of double bonds, and lipophilicity of the fatty acid skeleton
-
-
?
additional information
?
-
FAAH is the primary N-arachidonoylethanolamine-degrading enzyme, but it is also capable of hydrolyzing other bioactive N-acylethanolamines, such as N-palmitoylethanolamine, N-oleoylethanolamine and the sleep-inducing lipid oleamide
-
-
?
additional information
?
-
-
catalytic efficiency (kcat/Km) of FAAH for nonanoyl p-nitroanilide is approximately 50fold higher than for hexanoyl p-nitroanilide. NAI491 participates in hydrophobic binding interactions with medium-chain FAAH substrates. Use of p-nitroanilide substrates allows for the precise monitoring of enzymatic hydrolysis rates by following the increase in UV absorbance at 382 nm due to the release of p-nitroaniline. p-Nitroanilides are slower FAAH substrates than the corresponding primary amides, however, the binding affinities of these two classes of substrates are equivalent. Due to the slower rates of p-nitroanilide hydrolysis relative to the corresponding primary amides, it can be assumed that pNA substrates are hydrolyzed by FAAH in an acylation rate-limiting manner, allowing for the direct measurement of substrate binding constants through the determination of Km values
-
-
?
additional information
?
-
-
FAAH is an enzyme of broad substrate specificity and is capable of hydrolyzing a wide array of unsaturated, and to a lesser extent saturated, fatty acid primary amides. However, when substituted adjacent to the amide carbonyl, the substrates can be made sterically or electronically resistant to hydrolysis. Long chain saturated fatty acid amides are hydrolyzed slower than the corresponding Z unsaturated fatty acid amides and the rate of hydrolysis increases incrementally with increases in the degree of unsaturation
-
-
?
additional information
?
-
-
hybrid quantum mechanics/molecular mechanics (QM/MM) calculations reveal a new mechanism of nucleophile activation involving a Lys–Ser–Ser catalytic triad. The proposed mechanism, shows that Lys142 and cis-Ser217 have a direct role in the activation of Ser241, in agreement with kinetic labelling experiments employing the highly reactive fluorophosphonatetetramethyl rhodamine. The greater reduction of Ser241 labelling rate in the K142A/S217A double mutant, compared to the K142A and S217A single mutants, suggests that Lys142 and Ser217 cooperate to deprotonate Ser241
-
-
?
additional information
?
-
-
N,N-bis(2-hydroxyethyl)arachidonamide is not hydrolyzed
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2-arachidonoylglycerol + H2O
?
-
FAAH is responsible for approximately one-half of the 2-arachidonoylglycerol hydrolysis occurring in BV-2 cell homogenate
-
-
?
palmitoylethanolamide + H2O
palmitic acid + ethanolamine
-
substrate of FAAH and FAAH-2, the latter shows lower activity than FAAH
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
substrate of FAAH and FAAH-2, the latter shows lower activity than FAAH
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. N-arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. N-arachidonoylethanolamine
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
arachidonic acid + ethanolamine
-
i.e. arachidonoyl ethanolamide
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
FAAH-1 plays a primary role in regulating endocannabinoid signaling
-
-
?
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)
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
the enzyme cleaves anandamide and regulates in vivo the magnitude and duration of the signaling induced by this lipid messenger
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
enzyme is responsible for the catabolism of neuromodulatory fatty acid amides, including anandamide and oleamide
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
the enzyme is responsible for the hydrolysis of a number of neuromodulatory fatty acid amides, including the endogenous cannabinoid anandamide and the sleep-inducing lipid oleamide
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
the serine hydrolase is responsible for the degradation of endogenous oleamide and anandamide, fatty acid amides that function as chemical messengers
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
-
-
?
anandamide + H2O
ethanolamine + arachidonic acid
-
-
-
?
N-arachidonoylethanolamine + H2O
arachidonic acid + ethanolamine
-
-
-
?
N-arachidonoylethanolamine + H2O
arachidonic acid + ethanolamine
-
-
-
?
N-arachidonoylethanolamine + H2O
arachidonic acid + ethanolamine
-
-
-
?
oleamide + H2O
oleic acid + NH3
-
fatty acid amide hydrolase is a modulator of endogenous signaling compounds affecting sleep (oleamide) and analgesia (anandamide)
-
-
?
oleamide + H2O
oleic acid + NH3
-
enzyme is responsible for the catabolism of neuromodulatory fatty acid amides, including anandamide and oleamide
-
-
?
oleamide + H2O
oleic acid + NH3
-
role of FAAH in epithelial cells of the choroid plexus may be to control the concentration of oleamide in the cerebrospinal fluid. FAAH may exert an important regulatory role in shaping the duration and magnitude of the sleep-inducing effect of endogenously or exogenously derived oleamide
-
-
?
oleamide + H2O
oleic acid + NH3
-
the enzyme is responsible for the hydrolysis of a number of neuromodulatory fatty acid amides, including the endogenous cannabinoid anandamide and the sleep-inducing lipid oleamide
-
-
?
oleamide + H2O
oleic acid + NH3
-
the serine hydrolase is responsible for the degradation of endogenous oleamide and anandamide, fatty acid amides that function as chemical messengers
-
-
?
additional information
?
-
-
FAAH inactivates anandamide and other bioactive N-acylethanolamines
-
-
?
additional information
?
-
FAAH is the primary N-arachidonoylethanolamine-degrading enzyme, but it is also capable of hydrolyzing other bioactive N-acylethanolamines, such as N-palmitoylethanolamine, N-oleoylethanolamine and the sleep-inducing lipid oleamide
-
-
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(1-benzhydryltriazol-4-yl)methyl N-cyclohexylcarbamate
73% inhibition at 0.1 mM
(1-benzothiophen-6-ylamino)([(E)-[1-(biphenyl-3-yl)ethylidene]amino]oxy)methanone
-
-
(1-benzylpiperidin-4-yl)[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl]methanone
(1H-benzo[d][1,2,3]triazol-1-yl)(4-(3-phenoxybenzyl)-piperazin-1-yl)-methanone
-
(1H-benzo[d][1,2,3]triazol-1-yl)(4-(4-phenoxybenzyl)-piperazin-1-yl)-methanone hydrochloride
-
(1H-imidazol-1-yl)(4-(4-phenoxy-benzyl)-piperazin-1-yl)-methanone hydrochloride
-
(3H-[1,2,3]triazol[4,5-b]pyridin-3-yl)(4-(3-phenoxybenzyl)-piperazin-1-yl)-methanone
-
(3R,4R)-4-acetoxy-3-((10R)-(t-butyldimethylsilyloxy)-ethyl)-azetidin-2-one
-
(4-(bis(benzo[d][1,3]dioxol-5-yl)(hydroxy)methyl)-piperidin-1-yl)(1H-1,2,4-triazol-1-yl)methanone
-
(4-benzhydrylpiperazin-1-yl)(4-phenyl-1H-imidazol-1-yl)methanone
62% activity remaining at 0.01 mM
(4-benzylpiperazin-1-yl)[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl]methanone
(5-iodo-1,3-oxazol-2-yl)[(3R)-7-phenoxy-3,4-dihydro-2H-chromen-3-yl]methanone
-
(5-iodo-1,3-oxazol-2-yl)[(3S)-7-phenoxy-3,4-dihydro-2H-chromen-3-yl]methanone
-
(5E)-5-(4-methoxybenzylidene)-3-[1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indol-5-yl]-1,3-thiazolidine-2,4-dione
-
-
(5Z,8Z,11Z,14Z)-1-[1,3]oxazolo[4,5-b]pyridin-2-ylicosa-5,8,11,14-tetraen-1-one
-
-
(5Z,8Z,11Z,14Z)-1-[1,3]oxazolo[4,5-c]pyridin-2-ylicosa-5,8,11,14-tetraen-1-one
-
-
(5Z,8Z,11Z,14Z)-1-[1,3]oxazolo[5,4-c]pyridin-2-ylicosa-5,8,11,14-tetraen-1-one
-
-
(5Z,8Z,11Z,14Z)-N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)icosa-5,8,11,14-tetraenamide
-
-
(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
(5Z,8Z,11Z,14Z)-N-[(2R)-tetrahydrofuran-2-ylmethyl]icosa-5,8,11,14-tetraenamide
-
-
(5Z,8Z,11Z,14Z)-N-[(2S)-tetrahydrofuran-2-ylmethyl]icosa-5,8,11,14-tetraenamide
-
-
(6aR,10aR)-3-(1,1-dimethylheptyl)-9-(hydroxymethyl)-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol
-
-
(dodecylamino)[[(E)-[1-[3-(thiophen-2-yl)phenyl]ethylidene]amino]oxy]methanone
-
-
(phenylamino)[[(E)-[1-[3-(thiophen-2-yl)phenyl]ethylidene]amino]oxy]methanone
-
-
(phenylamino)[[(E)-[1-[4-(thiophen-2-yl)phenyl]ethylidene]amino]oxy]methanone
-
-
(S)-(4-oxo-1-pent-4-enoylazetidin-2-yl)methyl 3-(1H-indol-3-yl)propanoate
-
([(E)-[1-(2,2'-bithiophen-5-yl)ethylidene]amino]oxy)(naphthalen-1-ylamino)methanone
-
-
([(E)-[1-(4-cyclohexylphenyl)ethylidene]amino]oxy)(naphthalen-1-ylamino)methanone
-
-
([(E)-[1-(biphenyl-3-yl)ethylidene]amino]oxy)(naphthalen-1-ylamino)methanone
-
-
([(E)-[1-(biphenyl-3-yl)ethylidene]amino]oxy)[(4-fluorophenyl)amino]methanone
-
-
([(E)-[1-(biphenyl-3-yl)ethylidene]amino]oxy)[(4-methoxyphenyl)amino]methanone
-
-
([(E)-[1-(biphenyl-3-yl)ethylidene]amino]oxy)[(5-phenylpentyl)amino]methanone
-
-
([(E)-[1-(biphenyl-4-yl)ethylidene]amino]oxy)(naphthalen-1-ylamino)methanone
-
-
1,1,1,3,3,3-hexafluoropropan-2-yl 4-(3-phenoxybenzyl)piperazine-1-carboxylate
-
1,1,1-trifluoro-N-([1-[2-oxo-3-(4-phenoxyphenoxy)propyl]-1H-indazol-5-yl]carbamoyl)methanesulfonamide
1,2,3,4-tetrahydronaphthalen-1-yl [4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]carbamate
-
59.6% inhibition at 0.01 mM
1,3-oxazol-2-yl[(2R)-6-phenoxy-3,4-dihydro-2H-chromen-2-yl]methanone
-
1,3-oxazol-2-yl[(2S)-6-phenoxy-3,4-dihydro-2H-chromen-2-yl]methanone
-
1,3-oxazol-2-yl[(3R)-7-phenoxy-3,4-dihydro-2H-chromen-3-yl]methanone
-
1,3-oxazol-2-yl[(3R)-7-phenyl-3,4-dihydro-2H-chromen-3-yl]methanone
-
1,3-oxazol-2-yl[(3S)-7-phenoxy-3,4-dihydro-2H-chromen-3-yl]methanone
-
1,3-oxazol-2-yl[(3S)-7-phenyl-3,4-dihydro-2H-chromen-3-yl]methanone
-
1-(1-phenyl-1,2,4-triazol-3-yl)methyl N-cyclohexylcarbamate
70% inhibition at 0.1 mM
1-(2-oxo-3-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propyl)-1H-indole-5-carboxylic acid
-
21% inhibition at 0.01 mM
1-(2-oxo-3-[[4'-(propan-2-yl)biphenyl-4-yl]oxy]propyl)-1H-indole-5-carboxylic acid
-
-
1-(4-benzylpiperazin-1-yl)-2-[4-(2-methylpropyl)phenyl]propan-1-one
18% inhibition at 0.1 mM
1-benzothiophen-4-yl [4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]carbamate
-
-
1-[(3R)-1-[4-(1-benzofuran-2-yl)pyrimidin-2-yl]piperidin-3-yl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one
-
-
1-[(3S)-1-[4-(1-benzofuran-2-yl)pyrimidin-2-yl]piperidin-3-yl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one
1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl 3-(1H-indol-3-yl)propanoate
-
1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl 4-(pyridin-2-yl)butanoate
-
1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl 4-(pyridin-4-yl)butanoate
-
1-[(3S)-2-oxo-1-(pent-4-enoyl)azetidin-3-yl]ethyl biphenyl-4-carboxylate
-
1-[1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indol-5-yl]-1H-benzimidazole-7-carboxylic acid
-
-
1-[2-oxo-3-[4-(2-phenoxyethoxy)phenoxy]propyl]-1H-indole-5-carboxylic acid
-
-
1-[2-oxo-3-[4-(2-phenylpropan-2-yl)phenoxy]propyl]-1H-indole-5-carboxylic acid
-
-
1-[3-[(3'-chlorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
-
1-[3-[(3'-fluorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
-
1-[3-[(3-chlorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
-
1-[3-[(3-fluorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
-
1-[3-[(3-methoxybiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
-
1-[3-[(3-methylbiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
39% inhibition at 0.01 mM
1-[3-[(4'-fluorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
-
1-[3-[(4'-methoxybiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
-
1-[3-[(4'-methylbiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
-
1-[3-[4-(4-fluorophenyl)phenoxy]-2-oxopropyl]indazole-5-carboxylic acid
-
-
1-[4-(2,3-dimethylphenyl)piperazin-1-yl]-2-[4-(2-methylpropyl)phenyl]propan-1-one
-
1-[4-(2-methylphenyl)piperazin-1-yl]-2-[4-(2-methylpropyl)phenyl]propan-1-one
33% inhibition at 0.1 mM
1-[4-(3,4-dichlorophenyl)piperazin-1-yl]-2-[4-(2-methylpropyl)phenyl]propan-1-one
-
1-[4-(3-chlorophenyl)piperazin-1-yl]-2-[4-(2-methylpropyl)phenyl]propan-1-one
-
1-[4-(3-methoxyphenyl)piperazin-1-yl]-2-[4-(2-methylpropyl)phenyl]propan-1-one
41% inhibition at 0.1 mM
1-[4-(3-methylphenyl)piperazin-1-yl]-2-[4-(2-methylpropyl)phenyl]propan-1-one
-
1-[4-(4-chlorophenyl)piperazin-1-yl]-2-[4-(2-methylpropyl)phenyl]propan-1-one
-
1-[4-(4-fluorophenyl)piperazin-1-yl]-2-[4-(2-methylpropyl)phenyl]propan-1-one
-
1-[4-(4-methoxyphenyl)piperazin-1-yl]-2-[4-(2-methylpropyl)phenyl]propan-1-one
-
1-[4-[(3-chlorophenyl)methyl]piperazin-1-yl]-2-[4-(2-methylpropyl)phenyl]propan-1-one
8% inhibition at 0.1 mM
1-[4-[bis(1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidin-1-yl]-3,3,3-trifluoro-2-(trifluoromethyl)propan-1-one
-
1-[5-(2,4-dimethoxypyrimidin-5-yl)-1,3-oxazol-2-yl]-7-phenylheptan-1-one
-
-
1-[5-(2,6-dimethoxypyrimidin-4-yl)-1,3-oxazol-2-yl]-7-phenylheptan-1-one
-
-
1-[5-(3-benzyl-1,2,4-oxadiazol-5-yl)-1H-indol-1-yl]-3-(4-octylphenoxy)propan-2-one
-
-
1-[5-(3-ethyl-1,2,4-oxadiazol-5-yl)-1H-indol-1-yl]-3-(4-octylphenoxy)propan-2-one
-
-
1-[5-(morpholin-4-ylcarbonyl)-1H-indol-1-yl]-3-(4-octylphenoxy)propan-2-one
-
-
1-[5-[(4-methylpiperazin-1-yl)carbonyl]-1,3-oxazol-2-yl]-7-phenylheptan-1-one
-
-
1H-benzimidazol-4-yl [4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]carbamate
-
-
2,2,2-trichloroethyl 4-(bis(benzo[d][1,3]dioxol-5-yl)(hydroxy)methyl)piperidine-1-carboxylate
-
2,2-dimethyl-1,3-dioxolan-4-ylmethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
-
-
2,3-dihydro-1,4-benzodioxin-5-yl [4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]carbamate
-
-
2-(2-fluorobiphenyl-4-yl)-N-(2-(3-methylpyridin-2-ylamino)-2-oxoethyl)propanamide
-
2-(2-fluorobiphenyl-4-yl)-N-(3-methylpyridin-2-yl)propanamide
mode of inhibition, overview. Flu-AM1 does not inhibit the enzyme from brain in vivo
2-(4-cyclohexylphenoxy)-N-[2-(1H-imidazo[4,5-b]pyridin-2-yl)phenyl]acetamide
-
2-(4-cyclohexylphenoxy)-N-[3-(1H-imidazo[4,5-b]pyridin-2-yl)phenyl]acetamide
-
2-(4-cyclohexylphenoxy)-N-[3-([1,3]oxazolo[4,5-b]pyridin-2-yl)phenyl]acetamide
-
2-(4-cyclohexylphenoxy)-N-[4-(1H-imidazo[4,5-b]pyridin-2-yl)phenyl]acetamide
-
2-(4-cyclohexylphenoxy)-N-[4-([1,3]oxazolo[4,5-b]pyridin-2-yl)phenyl]acetamide
-
2-(5,5-dimethyl-1,3-dioxan-2-yl)ethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
-
-
2-methyl-N-(3-methylpyridin-2-yl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
2-[([1,1'-biphenyl]-4-yl)oxy]-N-[2-(1H-imidazo[4,5-b]pyridin-2-yl)phenyl]acetamide
-
2-[([1,1'-biphenyl]-4-yl)oxy]-N-[3-(1H-imidazo[4,5-b]pyridin-2-yl)phenyl]acetamide
-
2-[([1,1'-biphenyl]-4-yl)oxy]-N-[3-([1,3]oxazolo[4,5-b]pyridin-2-yl)phenyl]acetamide
-
2-[([1,1'-biphenyl]-4-yl)oxy]-N-[4-(1H-imidazo[4,5-b]pyridin-2-yl)phenyl]acetamide
-
2-[4-(2-methylpropyl)phenyl]-1-(4-phenylpiperazin-1-yl)propan-1-one
-
2-[4-(2-methylpropyl)phenyl]-N-[[3-(trifluoromethyl)phenyl]methyl]propanamide
-
2-[4-(2-methylpropyl)phenyl]-N-[[4-(trifluoromethyl)phenyl]methyl]propanamide
-
2-[[(2E)-hex-2-en-1-yl]oxy]-N-[2-(1H-imidazo[4,5-b]pyridin-2-yl)phenyl]acetamide
-
2-[[(2E)-hex-2-en-1-yl]oxy]-N-[3-(1H-imidazo[4,5-b]pyridin-2-yl)phenyl]acetamide
-
2-[[(2E)-hex-2-en-1-yl]oxy]-N-[3-([1,3]oxazolo[4,5-b]pyridin-2-yl)phenyl]acetamide
-
2-[[(2E)-hex-2-en-1-yl]oxy]-N-[4-(1H-imidazo[4,5-b]pyridin-2-yl)phenyl]acetamide
-
3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-ethyl-N-(2-hydroxyethyl)azetidine-1-carboxamide
3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methyl-N-(2-phenylethyl)azetidine-1-carboxamide
3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methyl-N-phenylazetidine-1-carboxamide
4-(acetylamino)phenyl (4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)acetate
-
-
4-(acetylamino)phenyl 2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanoate
-
competitive, also able to inhibit the FAAH activity in rat basophilic leukemia cells as assessed by measuring either the hydrolysis of anandamide, the FAAH-dependent cellular accumulation of anandamide, or the FAAH-dependent recycling of tritium to the cellmembranes
4-(acetylamino)phenyl 2-[[2-(trifluoromethyl)pyridin-4-yl]amino]pyridine-3-carboxylate
-
-
4-(acetylamino)phenyl 2-[[3-(trifluoromethyl)phenyl]amino]pyridine-3-carboxylate
-
-
4-(acetylamino)phenyl 2-{[2-(trifluoromethyl)pyridin-4-yl]amino}benzoate
-
-
4-(acetylamino)phenyl 3-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanoate
-
-
4-(acetylamino)phenyl 3-methyl-4-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
-
-
4-(acetylamino)phenyl 3-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
-
-
4-(acetylamino)phenyl 4-([[2-(trifluoromethyl)pyridin-4-yl]amino]methyl)benzoate
-
-
4-(acetylamino)phenyl 4-chloro-2-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
-
-
4-(acetylamino)phenyl 4-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
-
-
4-(acetylamino)phenyl 5-chloro-2-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
-
-
4-(acetylamino)phenyl 5-methyl-2-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
-
-
4-(acetylamino)phenyl N-(3-methyl-4-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoyl)glycinate
-
-
4-(acetylamino)phenyl N-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoyl)glycinate
-
-
4-(acetylamino)phenyl N-[(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)acetyl]glycinate
-
-
4-(acetylamino)phenyl N-[2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanoyl]glycinate
-
-
4-benzhydryl-N-(4-(trifluoromethyl)phenyl)piperazine-1-carboxamide
86% activity remaining at 0.01 mM
4-benzhydryl-N-(4-butylphenyl)piperazine-1-carboxamide
84% activity remaining at 0.01 mM
4-benzhydryl-N-(4-methoxyphenyl)piperazine-1-carboxamide
89% activity remaining at 0.01 mM
4-benzhydryl-N-(4-nitrophenyl)piperazine-1-carboxamide
84% activity remaining at 0.01 mM
4-benzhydryl-N-(pyridin-2-yl)piperazine-1-carboxamide
87% activity remaining at 0.01 mM
4-benzhydryl-N-(pyridin-3-yl)piperazine-1-carboxamide
87% activity remaining at 0.01 mM
4-benzhydryl-N-phenylpiperazine-1-carboxamide
88% activity remaining at 0.01 mM
4-carbamoylnaphthalen-1-yl [4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]carbamate
-
-
4-fluoronaphthalen-1-yl [4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]carbamate
-
-
4-hydroxynaphthalen-1-yl [4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]carbamate
-
-
4-methoxynaphthalen-1-yl [4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]carbamate
-
-
4-nitrophenyl 4-[bis(1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate
-
4-nitrophenyl-4-(bis(benzo[d][1,3]dioxol-5-yl)methyl)piperidine-1-carboxylate
-
4-[([4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]carbamoyl)oxy]naphthalene-1-carboxylic acid
-
-
4-[4-(2,4-difluorophenyl)-1,3-thiazol-2-yl]-N-(3,4-dimethyl-1,2-oxazol-5-yl)piperazine-1-carboxamide
5,6,7,8-tetrahydronaphthalen-1-yl [4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl]carbamate
-
-
5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-morpholin-4-yl-1H-pyrazole-3-carboxamide
-
-
7-phenyl-1-[5-(thiomorpholin-4-ylcarbonyl)-1,3-oxazol-2-yl]heptan-1-one
-
-
7-phenyl-1-[5-[4-(trifluoromethyl)pyridin-2-yl]-1,3-oxazol-2-yl]heptan-1-one
-
-
benzyl 4-(dibenzo[d][1,3]dioxol-5-yl(hydroxy)methyl)-piperidine-1-carboxylate
-
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
ethoxy oleoyl fluorophosphonate
-
irreversible inhibitor, exclusively modifies FAAH at S241
ethyl 4-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-ylcarbonyl)piperazine-1-carboxylate
-
methyl 5-[2-(7-phenylheptanoyl)-1,3-oxazol-5-yl]thiophene-2-carboxylate
-
-
methyl 6-(2-[[(2R)-6-phenoxy-3,4-dihydro-2H-chromen-2-yl]carbonyl]-1,3-oxazol-5-yl)pyridine-2-carboxylate
-
methyl 6-(2-[[(2S)-6-phenoxy-3,4-dihydro-2H-chromen-2-yl]carbonyl]-1,3-oxazol-5-yl)pyridine-2-carboxylate
-
methyl 6-(2-[[(3R)-7-phenoxy-3,4-dihydro-2H-chromen-3-yl]carbonyl]-1,3-oxazol-5-yl)pyridine-2-carboxylate
-
methyl 6-(2-[[(3S)-7-phenoxy-3,4-dihydro-2H-chromen-3-yl]carbonyl]-1,3-oxazol-5-yl)pyridine-2-carboxylate
-
N,N-dimethyl-1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-carboxamide
-
-
N,N-dimethyl-1-[3-(4-octylphenoxy)-2-oxopropyl]-1H-indole-5-sulfonamide
-
-
N-(1,4-dihydroquinolin-8-yl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-(2-methylphenyl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-(3,4-dimethyl-1,2-oxazol-5-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide
N-(3-bromopyridin-2-yl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-(3-chloropyridin-2-yl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-(3-iodopyridin-2-yl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-(3-methylpyridin-2-yl)-1-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)cyclobutane-1-carboxamide
-
N-(3-methylpyridin-2-yl)-1-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)cyclohexane-1-carboxamide
30% inhibition at 0.1 mM
N-(3-methylpyridin-2-yl)-1-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)cyclopentane-1-carboxamide
-
N-(3-methylpyridin-2-yl)-1-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)cyclopropane-1-carboxamide
-
N-(3-methylpyridin-2-yl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)acetamide
-
N-(3-methylpyridin-2-yl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-(3-methylpyridin-2-yl)-2-(4-[[7-(trifluoromethyl)quinolin-4-yl]amino]phenyl)propanamide
-
N-(3-methylpyridin-2-yl)-2-(4-[[8-(trifluoromethyl)quinolin-4-yl]amino]phenyl)propanamide
-
N-(4-hydroxy-2-methylphenyl) arachidonoyl amide
-
i.e. VDM11, inhibits the metabolism of anandamide by rat brain FAAH. Inhibition may at least in part be a consequence of the compound acting as an alternative substrate
N-(4-hydroxyphenyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
-
i.e. AM404, a bioactive N-acylphenolamine, derived from paracetamol, competitve inhibition
N-(4-hydroxyphenyl)arachidonylamide
-
i.e. AM404, inhibits the metabolism of anandamide by rat brain FAAH
N-(4-methylpyridin-2-yl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-(5-methylpyridin-2-yl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-(phenylcarbamoyl)-3'-[(1E)-N-[(phenylcarbamoyl)oxy]ethanimidoyl]biphenyl-3-carboxamide
-
-
N-(pyrazin-2-yl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-(pyridazin-3-yl)-4-(3-[[5-(trifluoromethyl)pyridin-2-yl]oxy]benzylidene)piperidine-1-carboxamide
N-(pyridin-2-yl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-(pyridin-3-yl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-(pyridin-3-yl)-4-(3-[[5-(trifluoromethyl)pyridin-2-yl]oxy]benzyl)piperidine-1-carboxamide
-
N-(pyridin-4-yl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-(pyrimidin-2-yl)-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-benzyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-(2-hydroxyethyl)azetidine-1-carboxamide
N-benzyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methylazetidine-1-carboxamide
N-benzyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-[2-(dimethylamino)ethyl]azetidine-1-carboxamide
N-benzyl-3-[(R)-(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methylazetidine-1-carboxamide
N-benzyl-3-[(S)-(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methylazetidine-1-carboxamide
N-phenyl-4-(3-phenyl-4,5-dihydro-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide
-
N-[(2,4-dichlorophenyl)methyl]-2-[4-(2-methylpropyl)phenyl]propanamide
-
N-[(2,5-dichlorophenyl)methyl]-2-[4-(2-methylpropyl)phenyl]propanamide
-
N-[(2,6-dichlorophenyl)methyl]-2-[4-(2-methylpropyl)phenyl]propanamide
19% inhibition at 0.1 mM
N-[(2-chlorophenyl)methyl]-2-[4-(2-methylpropyl)phenyl]propanamide
-
N-[(2-methoxyphenyl)methyl]-2-[4-(2-methylpropyl)phenyl]propanamide
-
N-[(3,4-dichlorophenyl)methyl]-2-[4-(2-methylpropyl)phenyl]propanamide
-
N-[(3-hydroxy-4-methoxyphenyl)methyl]-2-[4-(2-methylpropyl)phenyl]propanamide
-
N-[(4-methoxyphenyl)methyl]-2-[4-(2-methylpropyl)phenyl]propanamide
-
N-[(pyridin-2-yl)methyl]-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-[(pyridin-3-yl)methyl]-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-[2-[(3-methylpyridin-2-yl)amino]-2-oxoethyl]-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-[3-(trifluoromethyl)pyridin-2-yl]-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-[3-([1,3]oxazolo[4,5-b]pyridin-2-yl)phenyl]-2-[4-(propan-2-yl)phenoxy]acetamide
-
N-[4-(2,3-dimethylphenyl)piperazin-1-yl]-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
24% inhibition at 0.1 mM
N-[4-(2-methylphenyl)piperazin-1-yl]-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
24% inhibition at 0.1 mM
N-[4-(4-chlorophenyl)piperazin-1-yl]-2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanamide
-
N-[4-(4-methoxy-1,3-benzothiazol-2-yl)phenyl]-1-(thiophen-2-ylsulfonyl)piperidine-4-carboxamide
naphthalen-1-yl (3-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propyl)carbamate
-
-
naphthalen-1-yl (4-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]butyl)carbamate
-
-
phenyl ([4-[(5-phenyl-2H-tetrazol-2-yl)methyl]phenyl]methyl)carbamate
-
phenyl 4-[2-(4-fluoro-1H-indol-1-yl)ethyl]piperidine-1-carboxylate
-
phenyl 4-[2-(5-chloro-1H-indol-1-yl)ethyl]piperidine-1-carboxylate
-
phenyl 4-[2-(5-fluoro-1H-indol-1-yl)ethyl]piperidine-1-carboxylate
-
phenyl 4-[2-(5-methoxy-1H-indol-1-yl)ethyl]piperidine-1-carboxylate
-
phenyl 4-[2-(5-methyl-1H-indol-1-yl)ethyl]piperidine-1-carboxylate
-
phenyl 4-[2-(6-fluoro-1H-indol-1-yl)ethyl]piperazine-1-carboxylate
-
phenyl 4-[2-(6-fluoro-1H-indol-1-yl)ethyl]piperidine-1-carboxylate
-
phenyl 4-[2-(7-fluoro-1H-indol-1-yl)ethyl]piperidine-1-carboxylate
-
piperidin-1-yl[[(E)-[1-[3-(thiophen-2-yl)phenyl]ethylidene]amino]oxy]methanone
-
-
tetrahydro-2H-pyran-2-ylmethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
-
-
[(2R)-6-phenoxy-3,4-dihydro-2H-chromen-2-yl][5-(pyridin-2-yl)-1,3-oxazol-2-yl]methanone
-
[(2S)-4-oxo-1-(pent-4-enoyl)azetidin-2-yl]methyl 4-(pyridin-2-yl)butanoate
-
[(2S)-4-oxo-1-(pent-4-enoyl)azetidin-2-yl]methyl 4-(pyridin-4-yl)butanoate
-
[(2S)-6-phenoxy-3,4-dihydro-2H-chromen-2-yl][5-(pyridin-2-yl)-1,3-oxazol-2-yl]methanone
-
[(3R)-7-(benzyloxy)-3,4-dihydro-2H-chromen-3-yl](1,3-oxazol-2-yl)methanone
-
[(3R)-7-(benzyloxy)-3,4-dihydro-2H-chromen-3-yl][5-(pyridin-2-yl)-1,3-oxazol-2-yl]methanone
-
[(3R)-7-phenoxy-3,4-dihydro-2H-chromen-3-yl][5-(pyridin-2-yl)-1,3-oxazol-2-yl]methanone
-
[(3R)-7-phenyl-3,4-dihydro-2H-chromen-3-yl][5-(pyridin-2-yl)-1,3-oxazol-2-yl]methanone
-
[(3S)-7-(benzyloxy)-3,4-dihydro-2H-chromen-3-yl](1,3-oxazol-2-yl)methanone
-
[(3S)-7-(benzyloxy)-3,4-dihydro-2H-chromen-3-yl][5-(pyridin-2-yl)-1,3-oxazol-2-yl]methanone
-
[(3S)-7-phenoxy-3,4-dihydro-2H-chromen-3-yl][5-(pyridin-2-yl)-1,3-oxazol-2-yl]methanone
-
[(3S)-7-phenyl-3,4-dihydro-2H-chromen-3-yl][5-(pyridin-2-yl)-1,3-oxazol-2-yl]methanone
-
[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
-
-
[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
-
-
[1-[(2-fluoro-3-methoxy-phenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
-
[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
-
[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
[3-[(2-chloropyridin-3-yl)(3,4-dichlorophenyl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
[3-[(2-chloropyridin-3-yl)(3-methoxyphenyl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](1,3-dihydro-2H-isoindol-2-yl)methanone
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](2-hydroxypiperidin-1-yl)methanone
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](2-methylpiperidin-1-yl)methanone
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](3,4-dihydroisoquinolin-2(1H)-yl)methanone
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](3-hydroxypiperidin-1-yl)methanone
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](3-hydroxypyrrolidin-1-yl)methanone
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](3-methylpiperidin-1-yl)methanone
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](4,4-difluoropiperidin-1-yl)methanone
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](4-fluoropiperidin-1-yl)methanone
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](4-hydroxypiperidin-1-yl)methanone
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](4-methylpiperazin-1-yl)methanone
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](4-methylpiperidin-1-yl)methanone
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
-
-
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](pyrrolidin-1-yl)methanone
[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl][4-(hydroxymethyl)piperidin-1-yl]methanone
[3-[(S)-(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
[3-[1,3-benzodioxol-5-yl(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
[4-[bis(1,3-benzodioxol-5-yl)methyl]piperidin-1-yl](1H-1,2,4-triazol-1-yl)methanone
-
[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl](1H-1,2,4-triazol-1-yl)methanone
-
[[(E)-[1-[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]ethylidene]amino]oxy](naphthalen-1-ylamino)methanone
-
-
(1-benzylpiperidin-4-yl)[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl]methanone
-
-
(1-benzylpiperidin-4-yl)[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl]methanone
-
-
(4-benzylpiperazin-1-yl)[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl]methanone
-
-
(4-benzylpiperazin-1-yl)[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl]methanone
-
-
1,1,1-trifluoro-N-([1-[2-oxo-3-(4-phenoxyphenoxy)propyl]-1H-indazol-5-yl]carbamoyl)methanesulfonamide
-
-
1,1,1-trifluoro-N-([1-[2-oxo-3-(4-phenoxyphenoxy)propyl]-1H-indazol-5-yl]carbamoyl)methanesulfonamide
-
1-[(3S)-1-[4-(1-benzofuran-2-yl)pyrimidin-2-yl]piperidin-3-yl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one
the compound belongs to the ketobenzimidazoles, though containing a carbonyl moiety, that do not covalently modify Ser241. These inhibitors achieve potent inhibition of FAAH activity primarily from shape complementarity to the active site and through numerous hydrophobic interactions exhibiting excellent selectivity and good pharmacokinetic properties, nonmechanism-based inhibition
1-[(3S)-1-[4-(1-benzofuran-2-yl)pyrimidin-2-yl]piperidin-3-yl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one
the compound belongs to the ketobenzimidazoles, though containing a carbonyl moiety, that do not covalently modify Ser241. These inhibitors achieve potent inhibition of FAAH activity primarily from shape complementarity to the active site and through numerous hydrophobic interactions exhibiting excellent selectivity and good pharmacokinetic properties, nonmechanism-based inhibition. Pharmacokinetic parameters and selectivity 2, overview
1-[3-(4-octylphenoxy)-2-oxopropyl]indole-5-carboxylic acid
-
structure-activity relationship, overview
1-[3-[(4'-chlorobiphenyl-4-yl)oxy]-2-oxopropyl]-1H-indole-5-carboxylic acid
-
-
2-(methylamino)-2-oxoethyl [2-[1-(6-methylpyridin-2-yl)piperidin-4-yl]ethyl]carbamate
-
2-(methylamino)-2-oxoethyl [2-[1-(6-methylpyridin-2-yl)piperidin-4-yl]ethyl]carbamate
-
3'-carbamoylbiphenyl-3-yl cyclohexylcarbamate
exerts a combination of anxiolytic-like, anti-depressant-like, and analgesic effects, due to its ability to inhibit FAAH activity in the CNS and peripheral tissues. Covalent enzyme binding at Ser241 leading to irreversible inhibition, the attack at the carbonyl group by Ser 241 leads to the formation of carbamoylated, catalytically inactive FAAH and releasing the O-biphenyl moiety as the leaving group
3'-carbamoylbiphenyl-3-yl cyclohexylcarbamate
covalent enzyme binding at Ser241 leading to irreversible inhibition, the attack at the carbonyl group by Ser 241 leads to the formation of carbamoylated, catalytically inactive FAAH and releasing the O-biphenyl moiety as the leaving group
3-pyridyl 4-(phenylcarbamoyl)piperidine-1-carboxylate
i.e. ASP8477; i.e. ASP8477
3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N,N-diethylazetidine-1-carboxamide
-
-
3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N,N-diethylazetidine-1-carboxamide
-
-
3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-ethyl-N-(2-hydroxyethyl)azetidine-1-carboxamide
-
-
3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-ethyl-N-(2-hydroxyethyl)azetidine-1-carboxamide
-
-
3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methyl-N-(2-phenylethyl)azetidine-1-carboxamide
-
-
3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methyl-N-(2-phenylethyl)azetidine-1-carboxamide
-
-
3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methyl-N-phenylazetidine-1-carboxamide
-
-
3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methyl-N-phenylazetidine-1-carboxamide
-
-
4-(3-phenyl-1,2,4-thiadiazol-5-yl)-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-(3-phenyl-1,2,4-thiadiazol-5-yl)-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-(3-phenyl-[1,2,4]thiadiazol-5-yl)piperazine-1-carboxylic acid phenylamide
-
4-(3-phenyl-[1,2,4]thiadiazol-5-yl)piperazine-1-carboxylic acid phenylamide
-
JNJ-1661010
4-[2-(2,4-difluorophenyl)pyridin-4-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[2-(2,4-difluorophenyl)pyridin-4-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[2-(2,4-difluorophenyl)pyrimidin-4-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[2-(2,4-difluorophenyl)pyrimidin-4-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[3-(4-chlorophenoxy)benzyl]-N-(pyridin-3-yl)piperazine-1-carboxamide
-
4-[4-(2,3-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(2,3-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(2,4-difluorophenyl)-1,3-thiazol-2-yl]-N-(3,4-dimethyl-1,2-oxazol-5-yl)piperazine-1-carboxamide
-
4-[4-(2,4-difluorophenyl)-1,3-thiazol-2-yl]-N-(3,4-dimethyl-1,2-oxazol-5-yl)piperazine-1-carboxamide
-
4-[4-(2,4-difluorophenyl)pyridin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(2,4-difluorophenyl)pyridin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(2,4-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(2,4-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(2,5-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(2,5-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(3,4-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
analgesic effect of 21d in rat inflammatory pain model, overview
4-[4-(3,4-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(3,5-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[4-(3,5-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[6-(2,4-difluorophenyl)pyridin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[6-(2,4-difluorophenyl)pyridin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[6-(2,4-difluorophenyl)pyrimidin-4-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
4-[6-(2,4-difluorophenyl)pyrimidin-4-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide
-
5-(4-hydroxyphenyl)pentanesulfonyl fluoride
i.e. AM3506, irreversible inhibitor for both the rat and the human enzyme, that covalently modifies the enzyme
5-(4-hydroxyphenyl)pentanesulfonyl fluoride
i.e. AM3506, irreversible inhibitor for both the rat and the human enzyme
6-bromo-N-(2-fluorophenyl)-1'H,4H-spiro[1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide
an irreversible covalent inhibitor, binding structure, overview
6-bromo-N-(2-fluorophenyl)-1'H,4H-spiro[1,3-benzodioxine-2,4'-piperidine]-1'-carboxamide
an irreversible covalent inhibitor, binding structure, overview
7-phenyl-1-[5-(pyridin-2-yl)-1,3-oxazol-2-yl]heptan-1-one
-
OL-135, an alpha-keto-heterocycle that is a covalent reversible inhibitor of FAAH
7-phenyl-1-[5-(pyridin-2-yl)-1,3-oxazol-2-yl]heptan-1-one
reversible inhibitor
7-phenyl-1-[5-(pyridin-2-yl)-1,3-oxazol-2-yl]heptan-1-one
-
OL-135, an alpha-keto-heterocycle that is a covalent reversible inhibitor of FAAH
7-phenyl-1-[5-(pyridin-2-yl)-1,3-oxazol-2-yl]heptan-1-one
i.e. OL-135, the enzyme inhibitor exhibits antinociceptive and anti-inflammatory activity and increases levels of anandamide in vivo
azepan-1-yl[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl]methanone
-
-
azepan-1-yl[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl]methanone
-
-
azetidin-1-yl[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl]methanone
-
-
azetidin-1-yl[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl]methanone
-
-
hexadecyl sulfonylfluoride
i.e. AM374, is a potent irreversible in vitro and in vivo inhibitor of fatty acid amide hydrolase
hexadecyl sulfonylfluoride
i.e. AM374, is a potent in vitro and in vivo inhibitor of fatty acid amide hydrolase
methyl arachidonyl fluorophosphonate
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MAFP, a potent irreversible FAAH inhibitor
N,N-dibenzyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidine-1-carboxamide
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N,N-dibenzyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidine-1-carboxamide
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N-(3,4-dimethyl-1,2-oxazol-5-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide
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N-(3,4-dimethyl-1,2-oxazol-5-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide
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N-(pyridazin-3-yl)-4-(3-[[5-(trifluoromethyl)pyridin-2-yl]oxy]benzylidene)piperidine-1-carboxamide
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N-(pyridazin-3-yl)-4-(3-[[5-(trifluoromethyl)pyridin-2-yl]oxy]benzylidene)piperidine-1-carboxamide
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N-([1-[2-oxo-3-(4-phenoxyphenoxy)propyl]-1H-indazol-5-yl]carbamoyl)benzenesulfonamide
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N-([1-[2-oxo-3-(4-phenoxyphenoxy)propyl]-1H-indazol-5-yl]carbamoyl)benzenesulfonamide
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N-([1-[2-oxo-3-(4-phenoxyphenoxy)propyl]-1H-indazol-5-yl]carbamoyl)methanesulfonamide
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N-([1-[2-oxo-3-(4-phenoxyphenoxy)propyl]-1H-indazol-5-yl]carbamoyl)methanesulfonamide
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N-benzyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-(2-hydroxyethyl)azetidine-1-carboxamide
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N-benzyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-(2-hydroxyethyl)azetidine-1-carboxamide
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N-benzyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methylazetidine-1-carboxamide
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N-benzyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methylazetidine-1-carboxamide
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N-benzyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-[2-(dimethylamino)ethyl]azetidine-1-carboxamide
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N-benzyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-[2-(dimethylamino)ethyl]azetidine-1-carboxamide
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N-benzyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidine-1-carboxamide
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N-benzyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidine-1-carboxamide
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N-benzyl-3-[(R)-(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methylazetidine-1-carboxamide
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N-benzyl-3-[(R)-(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methylazetidine-1-carboxamide
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N-benzyl-3-[(S)-(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methylazetidine-1-carboxamide
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N-benzyl-3-[(S)-(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]-N-methylazetidine-1-carboxamide
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N-phenyl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide
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N-tert-butyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidine-1-carboxamide
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N-tert-butyl-3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidine-1-carboxamide
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N-[1-[2-oxo-3-(4-phenoxyphenoxy)propyl]-1H-indazol-5-yl]-N'-phenylurea
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N-[4-(4-methoxy-1,3-benzothiazol-2-yl)phenyl]-1-(thiophen-2-ylsulfonyl)piperidine-4-carboxamide
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a reversible, albeit slowly dissociating inhibitor of FAAH, reversibly and noncovalently inhibiting, molecular docking and computational modeling of interactions of the benzothiazole analogue 1 with humanized rat FAAH by induced fit docking, overview. Failure to observe the formation of covalent enzyme-inhibitor adduct or putative cleavage product using electrospray mass spectrometric techniques
N-[4-(4-methoxy-1,3-benzothiazol-2-yl)phenyl]-1-(thiophen-2-ylsulfonyl)piperidine-4-carboxamide
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a reversible, albeit slowly dissociating inhibitor of FAAH, reversibly and noncovalently inhibiting, molecular docking and computational modeling of interactions of the benzothiazole analogue 1 with humanized rat FAAH by induced fit docking, overview. Failure to observe the formation of covalent enzyme-inhibitor adduct or putative cleavage product using electrospray mass spectrometric techniques
oleoyl oxazolopyridine
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i.e. oloxa, a potent noncompetitive inhibitor, almost complete inhibition at 50 nM
oleoyl oxazolopyridine
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, i.e. oloxa, a potent noncompetitive inhibitor, almost complete inhibition at 50 nM
PF-3845
crystal structure analysis of enzyme-inhibitor complex. The inhibitor interacts with the catalytic triad and oxyanion hole residues
URB597
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a carbamate inhibiting FAAH covalently and irreversibly, time-dependent inhibition, overview
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
URB597
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a carbamate inhibiting FAAH covalently and irreversibly, time-dependent inhibition, overview
URB597
a carbamate inhibitor that displays excellent selectivity for FAAH in the nervous system, although the inhibitor does inactivate additional peripheral hydrolases, enzyme-inhibitor binding structure, overview. The inhibitor interacts with the catalytic triad and oxyanion hole residues
[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
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[1-[(2,6-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
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[1-[(2-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
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[1-[(2-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
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[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
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[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
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[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
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[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
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[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
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[1-[(3,5-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
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[1-[(3,5-difluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
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[1-[(3,5-dimethoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
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[1-[(3,5-dimethoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
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[1-[(3-chlorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
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[1-[(3-fluorophenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
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[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-cyclohexylcarbamate
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[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
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[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(2-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
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[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
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[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
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[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
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[1-[(3-methoxyphenyl)methyl]triazol-4-yl]methyl N-[[1-[(4-methoxyphenyl)methyl]triazol-4-yl]methyl]carbamate
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[3-[(2-chlorophenyl)(4-chlorophenyl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
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[3-[(2-chlorophenyl)(4-chlorophenyl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
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[3-[(2-chloropyridin-3-yl)(2-methylphenyl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
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[3-[(2-chloropyridin-3-yl)(2-methylphenyl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
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[3-[(2-chloropyridin-3-yl)(3,4-dichlorophenyl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
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[3-[(2-chloropyridin-3-yl)(3,4-dichlorophenyl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
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[3-[(2-chloropyridin-3-yl)(3-methoxyphenyl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
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[3-[(2-chloropyridin-3-yl)(3-methoxyphenyl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
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[3-[(2-chloropyridin-3-yl)(phenyl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
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[3-[(2-chloropyridin-3-yl)(phenyl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
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[3-[(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
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[3-[(3-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
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[3-[(3-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](piperidin-1-yl)methanone
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[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](1,3-dihydro-2H-isoindol-2-yl)methanone
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[3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl](1,3-dihydro-2H-isoindol-2-yl)methanone