BRENDA - Enzyme Database show

Discovery and characterization of 2-acylaminoimidazole microsomal prostaglandin E synthase-1 inhibitors

Schiffler, M.A.; Antonysamy, S.; Bhattachar, S.N.; Campanale, K.M.; Chandrasekhar, S.; Condon, B.; Desai, P.V.; Fisher, M.J.; Groshong, C.; Harvey, A.; Hickey, M.J.; Hughes, N.E.; Jones, S.A.; Kim, E.J.; Kuklish, S.L.; Luz, J.G.; Norman, B.H.; Rathmell, R.E.; Rizzo, J.R.; Seng, T.W.; Thibodeaux, S.J.; Woods, T.A.; J. Med. Chem. 59, 194-205 (2016)

Data extracted from this reference:

Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
5.3.99.3
2-(6-chloro-1H-phenanthro[9,10-d]imidazol-2-yl)benzene-1,3-dicarbonitrile
fludrocortisone
Homo sapiens
5.3.99.3
2-(difluoromethyl)-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
-
Homo sapiens
5.3.99.3
2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]-N-[4-methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]pyridine-3-carboxamide
-
Homo sapiens
5.3.99.3
2-(difluoromethyl)-N-(1H-imidazol-2-yl)-5-([[(2R)-2-methylbutanoyl]amino]methyl)benzamide
-
Homo sapiens
5.3.99.3
2-(difluoromethyl)-N-(1H-imidazol-2-yl)-5-[(2-methylpropanamido)methyl]benzamide
-
Homo sapiens
5.3.99.3
2-(difluoromethyl)-N-[4-methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]-5-(propanamidomethyl)pyridine-3-carboxamide
-
Homo sapiens
5.3.99.3
2-bromo-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
-
Homo sapiens
5.3.99.3
2-chloro-4-fluoro-N-(1H-imidazol-2-yl)-5-[(2-methylpropanamido)methyl]benzamide
CEP-32496
Homo sapiens
5.3.99.3
2-chloro-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
-
Homo sapiens
5.3.99.3
2-chloro-5-[(3,3-dimethylbutanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
-
Homo sapiens
5.3.99.3
2-chloro-N-(1H-imidazol-2-yl)-4-methyl-5-[(2-methylpropanamido)methyl]benzamide
-
Homo sapiens
5.3.99.3
2-chloro-N-(1H-imidazol-2-yl)-5-[(2-methylpropanamido)methyl]benzamide
-
Homo sapiens
5.3.99.3
5-(acetamidomethyl)-2-(difluoromethyl)-N-[4-methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]pyridine-3-carboxamide
-
Homo sapiens
5.3.99.3
5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)-2-(trifluoromethyl)benzamide
-
Homo sapiens
5.3.99.3
5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)-2-methylbenzamide
-
Homo sapiens
5.3.99.3
N-[5-(4-chlorophenyl)-1H-imidazol-2-yl]-2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]benzamide
-
Homo sapiens
5.3.99.3
N-[5-(4-chlorophenyl)-1H-imidazol-2-yl]-2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]pyridine-3-carboxamide
-
Homo sapiens
5.3.99.3
N-[5-(4-chlorophenyl)-4-methyl-1H-imidazol-2-yl]-2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]pyridine-3-carboxamide
-
Homo sapiens
5.3.99.3
sodium 3-[1-[(4-chlorophenyl)methyl]-5-(2-fluoro[1,1'-biphenyl]-4-yl)-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoate
-
Homo sapiens
Localization
EC Number
Localization
Commentary
Organism
GeneOntology No.
Textmining
5.3.99.3
microsome
-
Homo sapiens
-
-
Natural Substrates/ Products (Substrates)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
5.3.99.3
Prostaglandin H2
Homo sapiens
-
Prostaglandin E2
-
-
?
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
5.3.99.3
Homo sapiens
-
-
-
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
5.3.99.3
Prostaglandin H2
-
748368
Homo sapiens
Prostaglandin E2
-
-
-
?
IC50 Value
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
5.3.99.3
0.0000009
-
at pH 7.0 and 25C
Homo sapiens
2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]-N-[4-methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]pyridine-3-carboxamide
5.3.99.3
0.000003
-
at pH 7.0 and 25C
Homo sapiens
N-[5-(4-chlorophenyl)-1H-imidazol-2-yl]-2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]benzamide
5.3.99.3
0.000003
-
at pH 7.0 and 25C
Homo sapiens
N-[5-(4-chlorophenyl)-1H-imidazol-2-yl]-2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]pyridine-3-carboxamide
5.3.99.3
0.000003
-
at pH 7.0 and 25C
Homo sapiens
N-[5-(4-chlorophenyl)-4-methyl-1H-imidazol-2-yl]-2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]pyridine-3-carboxamide
5.3.99.3
0.0000053
-
at pH 7.0 and 25C
Homo sapiens
2-(6-chloro-1H-phenanthro[9,10-d]imidazol-2-yl)benzene-1,3-dicarbonitrile
5.3.99.3
0.0000103
-
at pH 7.0 and 25C
Homo sapiens
2-(difluoromethyl)-N-[4-methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]-5-(propanamidomethyl)pyridine-3-carboxamide
5.3.99.3
0.0000195
-
at pH 7.0 and 25C
Homo sapiens
sodium 3-[1-[(4-chlorophenyl)methyl]-5-(2-fluoro[1,1'-biphenyl]-4-yl)-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoate
5.3.99.3
0.000074
-
at pH 7.0 and 25C
Homo sapiens
5-(acetamidomethyl)-2-(difluoromethyl)-N-[4-methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]pyridine-3-carboxamide
5.3.99.3
0.000198
-
at pH 7.0 and 25C
Homo sapiens
2-bromo-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
5.3.99.3
0.000241
-
at pH 7.0 and 25C
Homo sapiens
2-chloro-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
5.3.99.3
0.000385
-
at pH 7.0 and 25C
Homo sapiens
2-chloro-5-[(3,3-dimethylbutanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
5.3.99.3
0.000676
-
at pH 7.0 and 25C
Homo sapiens
2-(difluoromethyl)-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
5.3.99.3
0.000885
-
at pH 7.0 and 25C
Homo sapiens
2-chloro-N-(1H-imidazol-2-yl)-5-[(2-methylpropanamido)methyl]benzamide
5.3.99.3
0.00108
-
at pH 7.0 and 25C
Homo sapiens
5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)-2-(trifluoromethyl)benzamide
5.3.99.3
0.00112
-
at pH 7.0 and 25C
Homo sapiens
2-(difluoromethyl)-N-(1H-imidazol-2-yl)-5-([[(2R)-2-methylbutanoyl]amino]methyl)benzamide
5.3.99.3
0.00232
-
at pH 7.0 and 25C
Homo sapiens
2-chloro-N-(1H-imidazol-2-yl)-4-methyl-5-[(2-methylpropanamido)methyl]benzamide
5.3.99.3
0.00246
-
at pH 7.0 and 25C
Homo sapiens
2-(difluoromethyl)-N-(1H-imidazol-2-yl)-5-[(2-methylpropanamido)methyl]benzamide
5.3.99.3
0.00311
-
at pH 7.0 and 25C
Homo sapiens
5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)-2-methylbenzamide
5.3.99.3
0.00367
-
at pH 7.0 and 25C
Homo sapiens
2-chloro-4-fluoro-N-(1H-imidazol-2-yl)-5-[(2-methylpropanamido)methyl]benzamide
IC50 Value (protein specific)
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
5.3.99.3
0.0000009
-
at pH 7.0 and 25C
Homo sapiens
2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]-N-[4-methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]pyridine-3-carboxamide
5.3.99.3
0.000003
-
at pH 7.0 and 25C
Homo sapiens
N-[5-(4-chlorophenyl)-1H-imidazol-2-yl]-2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]benzamide
5.3.99.3
0.000003
-
at pH 7.0 and 25C
Homo sapiens
N-[5-(4-chlorophenyl)-1H-imidazol-2-yl]-2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]pyridine-3-carboxamide
5.3.99.3
0.000003
-
at pH 7.0 and 25C
Homo sapiens
N-[5-(4-chlorophenyl)-4-methyl-1H-imidazol-2-yl]-2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]pyridine-3-carboxamide
5.3.99.3
0.0000053
-
at pH 7.0 and 25C
Homo sapiens
2-(6-chloro-1H-phenanthro[9,10-d]imidazol-2-yl)benzene-1,3-dicarbonitrile
5.3.99.3
0.0000103
-
at pH 7.0 and 25C
Homo sapiens
2-(difluoromethyl)-N-[4-methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]-5-(propanamidomethyl)pyridine-3-carboxamide
5.3.99.3
0.0000195
-
at pH 7.0 and 25C
Homo sapiens
sodium 3-[1-[(4-chlorophenyl)methyl]-5-(2-fluoro[1,1'-biphenyl]-4-yl)-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoate
5.3.99.3
0.000074
-
at pH 7.0 and 25C
Homo sapiens
5-(acetamidomethyl)-2-(difluoromethyl)-N-[4-methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]pyridine-3-carboxamide
5.3.99.3
0.000198
-
at pH 7.0 and 25C
Homo sapiens
2-bromo-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
5.3.99.3
0.000241
-
at pH 7.0 and 25C
Homo sapiens
2-chloro-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
5.3.99.3
0.000385
-
at pH 7.0 and 25C
Homo sapiens
2-chloro-5-[(3,3-dimethylbutanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
5.3.99.3
0.000676
-
at pH 7.0 and 25C
Homo sapiens
2-(difluoromethyl)-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
5.3.99.3
0.000885
-
at pH 7.0 and 25C
Homo sapiens
2-chloro-N-(1H-imidazol-2-yl)-5-[(2-methylpropanamido)methyl]benzamide
5.3.99.3
0.00108
-
at pH 7.0 and 25C
Homo sapiens
5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)-2-(trifluoromethyl)benzamide
5.3.99.3
0.00112
-
at pH 7.0 and 25C
Homo sapiens
2-(difluoromethyl)-N-(1H-imidazol-2-yl)-5-([[(2R)-2-methylbutanoyl]amino]methyl)benzamide
5.3.99.3
0.00232
-
at pH 7.0 and 25C
Homo sapiens
2-chloro-N-(1H-imidazol-2-yl)-4-methyl-5-[(2-methylpropanamido)methyl]benzamide
5.3.99.3
0.00246
-
at pH 7.0 and 25C
Homo sapiens
2-(difluoromethyl)-N-(1H-imidazol-2-yl)-5-[(2-methylpropanamido)methyl]benzamide
5.3.99.3
0.00311
-
at pH 7.0 and 25C
Homo sapiens
5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)-2-methylbenzamide
5.3.99.3
0.00367
-
at pH 7.0 and 25C
Homo sapiens
2-chloro-4-fluoro-N-(1H-imidazol-2-yl)-5-[(2-methylpropanamido)methyl]benzamide
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
5.3.99.3
2-(6-chloro-1H-phenanthro[9,10-d]imidazol-2-yl)benzene-1,3-dicarbonitrile
fludrocortisone
Homo sapiens
5.3.99.3
2-(difluoromethyl)-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
-
Homo sapiens
5.3.99.3
2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]-N-[4-methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]pyridine-3-carboxamide
-
Homo sapiens
5.3.99.3
2-(difluoromethyl)-N-(1H-imidazol-2-yl)-5-([[(2R)-2-methylbutanoyl]amino]methyl)benzamide
-
Homo sapiens
5.3.99.3
2-(difluoromethyl)-N-(1H-imidazol-2-yl)-5-[(2-methylpropanamido)methyl]benzamide
-
Homo sapiens
5.3.99.3
2-(difluoromethyl)-N-[4-methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]-5-(propanamidomethyl)pyridine-3-carboxamide
-
Homo sapiens
5.3.99.3
2-bromo-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
-
Homo sapiens
5.3.99.3
2-chloro-4-fluoro-N-(1H-imidazol-2-yl)-5-[(2-methylpropanamido)methyl]benzamide
CEP-32496
Homo sapiens
5.3.99.3
2-chloro-5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
-
Homo sapiens
5.3.99.3
2-chloro-5-[(3,3-dimethylbutanamido)methyl]-N-(1H-imidazol-2-yl)benzamide
-
Homo sapiens
5.3.99.3
2-chloro-N-(1H-imidazol-2-yl)-4-methyl-5-[(2-methylpropanamido)methyl]benzamide
-
Homo sapiens
5.3.99.3
2-chloro-N-(1H-imidazol-2-yl)-5-[(2-methylpropanamido)methyl]benzamide
-
Homo sapiens
5.3.99.3
5-(acetamidomethyl)-2-(difluoromethyl)-N-[4-methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-yl]pyridine-3-carboxamide
-
Homo sapiens
5.3.99.3
5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)-2-(trifluoromethyl)benzamide
-
Homo sapiens
5.3.99.3
5-[(2,2-dimethylpropanamido)methyl]-N-(1H-imidazol-2-yl)-2-methylbenzamide
-
Homo sapiens
5.3.99.3
N-[5-(4-chlorophenyl)-1H-imidazol-2-yl]-2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]benzamide
-
Homo sapiens
5.3.99.3
N-[5-(4-chlorophenyl)-1H-imidazol-2-yl]-2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]pyridine-3-carboxamide
-
Homo sapiens
5.3.99.3
N-[5-(4-chlorophenyl)-4-methyl-1H-imidazol-2-yl]-2-(difluoromethyl)-5-[(2-methylpropanamido)methyl]pyridine-3-carboxamide
-
Homo sapiens
5.3.99.3
sodium 3-[1-[(4-chlorophenyl)methyl]-5-(2-fluoro[1,1'-biphenyl]-4-yl)-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoate
-
Homo sapiens
Localization (protein specific)
EC Number
Localization
Commentary
Organism
GeneOntology No.
Textmining
5.3.99.3
microsome
-
Homo sapiens
-
-
Natural Substrates/ Products (Substrates) (protein specific)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
5.3.99.3
Prostaglandin H2
Homo sapiens
-
Prostaglandin E2
-
-
?
Substrates and Products (Substrate) (protein specific)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
5.3.99.3
Prostaglandin H2
-
748368
Homo sapiens
Prostaglandin E2
-
-
-
?