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Literature summary for 3.5.1.99 extracted from

  • Onnis, V.; Congiu, C.; Bjoerklund, E.; Hempel, F.; Soederstroem, E.; Fowler, C.J.
    Synthesis and evaluation of paracetamol esters as novel fatty acid amide hydrolase inhibitors (2010), J. Med. Chem., 53, 2286-2298.
    View publication on PubMed
Search for more literature for 3.5.1.99

Inhibitors

Inhibitors Comment Organism Structure
(R,S)-ibuprofen
-
 Rattus norvegicus
4-(acetylamino)phenyl (4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)acetate
-
 Rattus norvegicus
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 Rattus norvegicus
4-(acetylamino)phenyl 2-[[2-(trifluoromethyl)pyridin-4-yl]amino]pyridine-3-carboxylate
-
 Rattus norvegicus
4-(acetylamino)phenyl 2-[[3-(trifluoromethyl)phenyl]amino]benzoate
-
 Rattus norvegicus
4-(acetylamino)phenyl 2-[[3-(trifluoromethyl)phenyl]amino]pyridine-3-carboxylate
-
 Rattus norvegicus
4-(acetylamino)phenyl 2-{[2-(trifluoromethyl)pyridin-4-yl]amino}benzoate
-
 Rattus norvegicus
4-(acetylamino)phenyl 3-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanoate
-
 Rattus norvegicus
4-(acetylamino)phenyl 3-methyl-4-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
-
 Rattus norvegicus
4-(acetylamino)phenyl 3-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
-
 Rattus norvegicus
4-(acetylamino)phenyl 4-([[2-(trifluoromethyl)pyridin-4-yl]amino]methyl)benzoate
-
 Rattus norvegicus
4-(acetylamino)phenyl 4-chloro-2-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
-
 Rattus norvegicus
4-(acetylamino)phenyl 4-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
-
 Rattus norvegicus
4-(acetylamino)phenyl 5-chloro-2-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
-
 Rattus norvegicus
4-(acetylamino)phenyl 5-methyl-2-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
-
 Rattus norvegicus
4-(acetylamino)phenyl N-(3-methyl-4-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoyl)glycinate
-
 Rattus norvegicus
4-(acetylamino)phenyl N-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoyl)glycinate
-
 Rattus norvegicus
4-(acetylamino)phenyl N-[(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)acetyl]glycinate
-
 Rattus norvegicus
4-(acetylamino)phenyl N-[2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanoyl]glycinate
-
 Rattus norvegicus
additional information paracetamol itself does not inhibit FAAH, but undergoes a FAAH-dependent two-step metabolic transformation in the brain, liver, and spinal cord to form the bioactive N-acylphenolamine AM404. Synthesis and evaluation of paracetamol ester enzyme inhibitors, structure-activity relationship studies, overview Rattus norvegicus
N-(3-methylpyridin-2-yl)-2-(4'-isobutylphenyl)propionamide i.e. Ibu-am5 Rattus norvegicus
N-(4-hydroxyphenyl)-5Z,8Z,11Z,14Z-eicosatetraenamide i.e. AM404, a bioactive N-acylphenolamine, derived from paracetamol, competitve inhibition Rattus norvegicus

Localization

Localization Comment Organism GeneOntology No. Textmining
membrane
-
 Rattus norvegicus 16020
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
anandamide + H2O Rattus norvegicus
-
 arachidonic acid + ethanolamine
-
 ?

Organism

Organism UniProt Comment Textmining
Rattus norvegicus
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
basophilic leukemia cell
-
 Rattus norvegicus
-
brain
-
 Rattus norvegicus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
anandamide + H2O
-
 Rattus norvegicus arachidonic acid + ethanolamine
-
 ?

Synonyms

Synonyms Comment Organism
FAAH
-
 Rattus norvegicus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Rattus norvegicus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
 assay at Rattus norvegicus

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00016
-
 4-(acetylamino)phenyl 2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanoate pH 7.4, 37°C Rattus norvegicus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0001
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl 2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanoate
0.00018
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl (4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)acetate
0.00073
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl N-[2-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanoyl]glycinate
0.00087
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl N-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoyl)glycinate
0.0013
-
 pH 7.4, 37°C Rattus norvegicus N-(3-methylpyridin-2-yl)-2-(4'-isobutylphenyl)propionamide
0.0015
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl 3-(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)propanoate
0.0026
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl N-[(4-[[2-(trifluoromethyl)pyridin-4-yl]amino]phenyl)acetyl]glycinate
0.0027
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl 4-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
0.003
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl N-(3-methyl-4-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoyl)glycinate
0.0043
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl 5-chloro-2-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
0.0046
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl 3-methyl-4-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
0.0087
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl 2-[[3-(trifluoromethyl)phenyl]amino]benzoate
0.022
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl 4-([[2-(trifluoromethyl)pyridin-4-yl]amino]methyl)benzoate
0.031
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl 4-chloro-2-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
0.038
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl 5-methyl-2-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
0.047
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl 3-[[2-(trifluoromethyl)pyridin-4-yl]amino]benzoate
0.058
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl 2-[[2-(trifluoromethyl)pyridin-4-yl]amino]pyridine-3-carboxylate
0.064
-
 pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl 2-{[2-(trifluoromethyl)pyridin-4-yl]amino}benzoate
0.26
-
 pH 7.4, 37°C Rattus norvegicus (R,S)-ibuprofen
0.3
-
 above, pH 7.4, 37°C Rattus norvegicus 4-(acetylamino)phenyl 2-[[3-(trifluoromethyl)phenyl]amino]pyridine-3-carboxylate

General Information

General Information Comment Organism
physiological function FAAH is the key hydrolytic enzyme for the endogenous cannabinoid receptor ligand anandamide Rattus norvegicus