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Literature summary extracted from

  • Terwege, T.; Hanekamp, W.; Garzinsky, D.; Koenig, S.; Koch, O.; Lehr, M.
    omega-Imidazolyl- and omega-tetrazolylalkylcarbamates as inhibitors of fatty acid amide hydrolase Biological activity and in vitro metabolic stability (2016), ChemMedChem, 11, 429-443 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.5.1.99 2-fluorophenyl [6-(5-phenyl-2H-tetrazol-2-yl)hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 3'-carbamoyl[1,1'-biphenyl]-3-yl cyclohexylcarbamate
-
 Rattus norvegicus
3.5.1.99 4-fluorophenyl [6-(5-phenyl-2H-tetrazol-2-yl)hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 4-methoxyphenyl [6-(5-phenyl-2H-tetrazol-2-yl)hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 additional information structure-activity relationship studies on a series of aryl N-(omega-imidazolyl- and omega-tetrazolylalkyl)carbamate inhibitors are investigated. A pronounced increase in inhibitory potency is observed if a phenyl residue attached to the carbamate oxygen atom is replaced by a pyridin-3-yl moiety. The most active compounds exhibit IC50 values in the low nanomolar range. Investigations on the metabolic properties of these inhibitors are performed. In rat liver homogenate and in porcine plasma, the extent of their degradation is shown to be strongly dependent on the kind of aryl residue bound to the carbamate as well as on the length and type of the alkyl spacer connecting the carbamate group with the heterocyclic system Rattus norvegicus
3.5.1.99 phenyl ([4-[(5-phenyl-2H-tetrazol-2-yl)methyl]phenyl]methyl)carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [2-[2-(5-phenyl-2H-tetrazol-2-yl)ethoxy]ethyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [5-(2-phenyl-1H-imidazol-1-yl)pentyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [5-(5-phenyl-2H-tetrazol-2-yl)pentyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-(1H-imidazol-1-yl)hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-(2-methyl-4,5-diphenyl-1H-imidazol-1-yl)hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-(2-phenyl-1H-imidazol-1-yl)hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-(4,5-diphenyl-1H-imidazol-1-yl)hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-(4-phenyl-1H-imidazol-1-yl)hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-(5-benzyl-2H-tetrazol-2-yl)hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-(5-phenyl-1H-imidazol-1-yl)hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-(5-phenyl-1H-tetrazol-1-yl)hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-(5-phenyl-2H-tetrazol-2-yl)hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-[2-(3-chlorophenyl)-1H-imidazol-1-yl]hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-[2-(3-fluorophenyl)-1H-imidazol-1-yl]hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-[2-(3-methoxyphenyl)-1H-imidazol-1-yl]hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-[2-(3-methylphenyl)-1H-imidazol-1-yl]hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-[2-(4-chlorophenyl)-1H-imidazol-1-yl]hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-[5-(2-chlorophenyl)-2H-tetrazol-2-yl]hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-[5-(4-chlorophenyl)-2H-tetrazol-2-yl]hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-[5-(pyridin-2-yl)-2H-tetrazol-2-yl]hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-[5-(pyridin-3-yl)-2H-tetrazol-2-yl]hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [6-[5-(pyridin-4-yl)-2H-tetrazol-2-yl]hexyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [7-(2-phenyl-1H-imidazol-1-yl)heptyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [7-(5-phenyl-2H-tetrazol-2-yl)heptyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [8-(2-phenyl-1H-imidazol-1-yl)octyl]carbamate
-
 Rattus norvegicus
3.5.1.99 phenyl [8-(5-phenyl-2H-tetrazol-2-yl)octyl]carbamate
-
 Rattus norvegicus
3.5.1.99 pyridin-3-yl [6-(5-phenyl-2H-tetrazol-2-yl)hexyl]carbamate
-
 Rattus norvegicus

Organism

EC Number Organism UniProt Comment Textmining
3.5.1.99 Rattus norvegicus P97612
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.5.1.99 brain
-
 Rattus norvegicus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.5.1.99 N-(2-hydroxyethyl)-4-pyren-1-ylbutanamide + H2O
-
 Rattus norvegicus 4-(pyren-1-yl)butanamide + ethylene glycol
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.5.1.99 FAAH
-
 Rattus norvegicus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.5.1.99 0.0000053
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus 4-methoxyphenyl [6-(5-phenyl-2H-tetrazol-2-yl)hexyl]carbamate
3.5.1.99 0.000011
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus pyridin-3-yl [6-(5-phenyl-2H-tetrazol-2-yl)hexyl]carbamate
3.5.1.99 0.000054
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-[2-(3-chlorophenyl)-1H-imidazol-1-yl]hexyl]carbamate
3.5.1.99 0.000075
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-[2-(3-methylphenyl)-1H-imidazol-1-yl]hexyl]carbamate
3.5.1.99 0.000081
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [7-(5-phenyl-2H-tetrazol-2-yl)heptyl]carbamate
3.5.1.99 0.000112
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus 3'-carbamoyl[1,1'-biphenyl]-3-yl cyclohexylcarbamate
3.5.1.99 0.000112
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-[2-(3-fluorophenyl)-1H-imidazol-1-yl]hexyl]carbamate
3.5.1.99 0.000112
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [8-(5-phenyl-2H-tetrazol-2-yl)octyl]carbamate
3.5.1.99 0.00018
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]hexyl]carbamate
3.5.1.99 0.000209
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-[5-(2-chlorophenyl)-2H-tetrazol-2-yl]hexyl]carbamate
3.5.1.99 0.00024
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [7-(2-phenyl-1H-imidazol-1-yl)heptyl]carbamate
3.5.1.99 0.00025
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-(5-benzyl-2H-tetrazol-2-yl)hexyl]carbamate
3.5.1.99 0.00026
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl ([4-[(5-phenyl-2H-tetrazol-2-yl)methyl]phenyl]methyl)carbamate
3.5.1.99 0.00028
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-[5-(pyridin-2-yl)-2H-tetrazol-2-yl]hexyl]carbamate
3.5.1.99 0.00029
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-(2-phenyl-1H-imidazol-1-yl)hexyl]carbamate
3.5.1.99 0.00029
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-[2-(3-methoxyphenyl)-1H-imidazol-1-yl]hexyl]carbamate
3.5.1.99 0.00033
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus 2-fluorophenyl [6-(5-phenyl-2H-tetrazol-2-yl)hexyl]carbamate
3.5.1.99 0.0004
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [8-(2-phenyl-1H-imidazol-1-yl)octyl]carbamate
3.5.1.99 0.00042
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-[2-(4-chlorophenyl)-1H-imidazol-1-yl]hexyl]carbamate
3.5.1.99 0.00043
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [5-(2-phenyl-1H-imidazol-1-yl)pentyl]carbamate
3.5.1.99 0.00047
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-(2-methyl-4,5-diphenyl-1H-imidazol-1-yl)hexyl]carbamate
3.5.1.99 0.00048
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-(5-phenyl-1H-imidazol-1-yl)hexyl]carbamate
3.5.1.99 0.00049
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [5-(5-phenyl-2H-tetrazol-2-yl)pentyl]carbamate
3.5.1.99 0.00049
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-(4,5-diphenyl-1H-imidazol-1-yl)hexyl]carbamate
3.5.1.99 0.00057
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-[5-(4-chlorophenyl)-2H-tetrazol-2-yl]hexyl]carbamate
3.5.1.99 0.00062
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-(5-phenyl-2H-tetrazol-2-yl)hexyl]carbamate
3.5.1.99 0.00065
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus 4-methoxyphenyl [6-(5-phenyl-2H-tetrazol-2-yl)hexyl]carbamate
3.5.1.99 0.00066
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus 4-fluorophenyl [6-(5-phenyl-2H-tetrazol-2-yl)hexyl]carbamate
3.5.1.99 0.00074
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-[5-(pyridin-3-yl)-2H-tetrazol-2-yl]hexyl]carbamate
3.5.1.99 0.00088
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-(4-phenyl-1H-imidazol-1-yl)hexyl]carbamate
3.5.1.99 0.0012
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-[5-(pyridin-4-yl)-2H-tetrazol-2-yl]hexyl]carbamate
3.5.1.99 0.0013
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-(5-phenyl-1H-tetrazol-1-yl)hexyl]carbamate
3.5.1.99 0.0052
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [2-[2-(5-phenyl-2H-tetrazol-2-yl)ethoxy]ethyl]carbamate
3.5.1.99 0.006
-
 50 mM Tris-HCl, containing 1 mM sodium EDTA, pH 7.4 at 20°C Rattus norvegicus phenyl [6-(1H-imidazol-1-yl)hexyl]carbamate

General Information

EC Number General Information Comment Organism
3.5.1.99 metabolism fatty acid amide hydrolase terminates the analgesic and anti-inflammatory effects of endocannabinoids such as anandamide Rattus norvegicus