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Literature summary for 3.4.14.5 extracted from

  • Yeh, T.K.; Tsai, T.Y.; Hsu, T.; Cheng, J.H.; Chen, X.; Song, J.S.; Shy, H.S.; Chiou, M.C.; Chien, C.H.; Tseng, Y.J.; Huang, C.Y.; Yeh, K.C.; Huang, Y.L.; Huang, C.H.; Huang, Y.W.; Wang, M.H.; Tang, H.K.; Chao, Y.S.; Chen, C.T.; Jiaang, W.T.
    (2S,4S)-1-[2-(1,1-dimethyl-3-oxo-3-pyrrolidin-1-yl-propylamino)acetyl]-4-fluoro-pyrrolidine-2-carbonitrile: a potent, selective, and orally bioavailable dipeptide-derived inhibitor of dipeptidyl peptidase IV (2010), Bioorg. Med. Chem. Lett., 20, 3596-3600.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
-
Homo sapiens
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile 66% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 30% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus
(2S)-1-([[2-methyl-4-oxo-4-(pyrrolidin-1-yl)butan-2-yl]amino]acetyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-([[2-methyl-4-oxo-4-(pyrrolidin-1-yl)butan-2-yl]amino]acetyl)pyrrolidine-2-carbonitrile
-
Rattus norvegicus
(2S)-1-[([4-[(3R)-3-hydroxypyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]amino)acetyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-[([4-[(3R)-3-hydroxypyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]amino)acetyl]pyrrolidine-2-carbonitrile
-
Rattus norvegicus
(2S)-1-[N-[4-(1,3-dihydro-2H-isoindol-2-yl)-2-methyl-4-oxobutan-2-yl]glycyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-[N-[4-(1,3-dihydro-2H-isoindol-2-yl)-2-methyl-4-oxobutan-2-yl]glycyl]pyrrolidine-2-carbonitrile
-
Rattus norvegicus
(2S)-1-[[(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S)-1-[[(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile 84% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 73% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus
(2S,4S)-1-[2-(1,1-dimethyl-3-oxo-3-pyrrolidin-1-yl-propylamino)acetyl]-4-fluoro-pyrrolidine-2-carbonitrile potent, selective, and orally bioavailable dipeptide-derived inhibitor of dipeptidyl peptidase IV Homo sapiens
(2S,4S)-1-[2-(1,1-dimethyl-3-oxo-3-pyrrolidin-1-yl-propylamino)acetyl]-4-fluoro-pyrrolidine-2-carbonitrile potent, selective, and orally bioavailable dipeptide-derived inhibitor of dipeptidyl peptidase IV, 82% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 70% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus
(2S,4S)-1-[N-[4-(3,6-dihydropyridin-1(2H)-yl)-2-methyl-4-oxobutan-2-yl]glycyl]-4-fluoropyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,4S)-1-[N-[4-(3,6-dihydropyridin-1(2H)-yl)-2-methyl-4-oxobutan-2-yl]glycyl]-4-fluoropyrrolidine-2-carbonitrile 85% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 70% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus
(2S,4S)-1-[N-[4-(7-azabicyclo[2.2.1]hept-7-yl)-2-methyl-4-oxobutan-2-yl]glycyl]-4-fluoropyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,4S)-1-[N-[4-(7-azabicyclo[2.2.1]hept-7-yl)-2-methyl-4-oxobutan-2-yl]glycyl]-4-fluoropyrrolidine-2-carbonitrile
-
Rattus norvegicus
(2S,4S)-1-[N-[4-(azepan-1-yl)-2-methyl-4-oxobutan-2-yl]glycyl]-4-fluoropyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,4S)-1-[N-[4-(azepan-1-yl)-2-methyl-4-oxobutan-2-yl]glycyl]-4-fluoropyrrolidine-2-carbonitrile
-
Rattus norvegicus
(2S,4S)-4-fluoro-1-(N-[2-methyl-4-[(2R)-2-methylpyrrolidin-1-yl]-4-oxobutan-2-yl]glycyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,4S)-4-fluoro-1-(N-[2-methyl-4-[(2R)-2-methylpyrrolidin-1-yl]-4-oxobutan-2-yl]glycyl)pyrrolidine-2-carbonitrile 75% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 48% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus
(2S,4S)-4-fluoro-1-(N-[2-methyl-4-[4-(methylsulfonyl)piperazin-1-yl]-4-oxobutan-2-yl]glycyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,4S)-4-fluoro-1-(N-[2-methyl-4-[4-(methylsulfonyl)piperazin-1-yl]-4-oxobutan-2-yl]glycyl)pyrrolidine-2-carbonitrile 64% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 7% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus
(2S,4S)-4-fluoro-1-(N-[4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]glycyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,4S)-4-fluoro-1-(N-[4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]glycyl)pyrrolidine-2-carbonitrile
-
Rattus norvegicus
(2S,4S)-4-fluoro-1-([[2-methyl-4-oxo-4-(1,3-thiazolidin-3-yl)butan-2-yl]amino]acetyl)pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,4S)-4-fluoro-1-([[2-methyl-4-oxo-4-(1,3-thiazolidin-3-yl)butan-2-yl]amino]acetyl)pyrrolidine-2-carbonitrile 77% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 56% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus
(2S,4S)-4-fluoro-1-[([4-[(3R)-3-fluoropyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]amino)acetyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,4S)-4-fluoro-1-[([4-[(3R)-3-fluoropyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]amino)acetyl]pyrrolidine-2-carbonitrile
-
Rattus norvegicus
(2S,4S)-4-fluoro-1-[([4-[(3R)-3-hydroxypyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]amino)acetyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,4S)-4-fluoro-1-[([4-[(3R)-3-hydroxypyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]amino)acetyl]pyrrolidine-2-carbonitrile 63% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 15% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus
(2S,4S)-4-fluoro-1-[([4-[(3S)-3-hydroxypyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]amino)acetyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,4S)-4-fluoro-1-[([4-[(3S)-3-hydroxypyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]amino)acetyl]pyrrolidine-2-carbonitrile
-
Rattus norvegicus
(2S,4S)-4-fluoro-1-[N-[2-methyl-4-(4-methylpiperazin-1-yl)-4-oxobutan-2-yl]glycyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,4S)-4-fluoro-1-[N-[2-methyl-4-(4-methylpiperazin-1-yl)-4-oxobutan-2-yl]glycyl]pyrrolidine-2-carbonitrile
-
Rattus norvegicus
(2S,4S)-4-fluoro-1-[N-[2-methyl-4-(morpholin-4-yl)-4-oxobutan-2-yl]glycyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,4S)-4-fluoro-1-[N-[2-methyl-4-(morpholin-4-yl)-4-oxobutan-2-yl]glycyl]pyrrolidine-2-carbonitrile 89% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 59% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus
(2S,4S)-4-fluoro-1-[N-[2-methyl-4-oxo-4-(4-oxopiperidin-1-yl)butan-2-yl]glycyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,4S)-4-fluoro-1-[N-[2-methyl-4-oxo-4-(4-oxopiperidin-1-yl)butan-2-yl]glycyl]pyrrolidine-2-carbonitrile
-
Rattus norvegicus
(2S,4S)-4-fluoro-1-[N-[2-methyl-4-oxo-4-(piperidin-1-yl)butan-2-yl]glycyl]pyrrolidine-2-carbonitrile
-
Homo sapiens
(2S,4S)-4-fluoro-1-[N-[2-methyl-4-oxo-4-(piperidin-1-yl)butan-2-yl]glycyl]pyrrolidine-2-carbonitrile 86% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 74% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus
(3R)-3-amino-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
-
Homo sapiens
(3R)-3-amino-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one 30% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 20% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus
3-([2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]amino)-N-(3,4-dimethoxyphenyl)-3-methylbutanamide
-
Homo sapiens
3-([2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]amino)-N-(3,4-dimethoxyphenyl)-3-methylbutanamide
-
Rattus norvegicus
3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-3-methyl-N-(pyridin-2-yl)butanamide
-
Homo sapiens
3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-3-methyl-N-(pyridin-2-yl)butanamide 87% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 31% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus
3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-N-(3,4-dimethoxyphenyl)-3-methylbutanamide
-
Homo sapiens
3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-N-(3,4-dimethoxyphenyl)-3-methylbutanamide 86% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 18% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose; 88% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 41% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus
3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-N-cyclopentyl-3-methylbutanamide
-
Homo sapiens
3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-N-cyclopentyl-3-methylbutanamide 81% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 60% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus
ethyl 4-[3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-3-methylbutanoyl]piperazine-1-carboxylate
-
Homo sapiens
ethyl 4-[3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-3-methylbutanoyl]piperazine-1-carboxylate
-
Rattus norvegicus
N-[(1S,2R)-2-(3-chlorophenyl)cyclopropyl]-3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-3-methylbutanamide
-
Homo sapiens
N-[(1S,2R)-2-(3-chlorophenyl)cyclopropyl]-3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-3-methylbutanamide 66% plasma DPP-IV inhibition after 30 min at 3 mg/kg oral dose, 30% plasma DPP-IV inhibition after 8 h at 3 mg/kg oral dose Rattus norvegicus

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-
Rattus norvegicus
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
blood plasma
-
Homo sapiens
-
blood plasma
-
Rattus norvegicus
-

Synonyms

Synonyms Comment Organism
CD26
-
Homo sapiens
CD26
-
Rattus norvegicus
dipeptidyl peptidase IV
-
Homo sapiens
dipeptidyl peptidase IV
-
Rattus norvegicus
DPP-IV
-
Homo sapiens
DPP-IV
-
Rattus norvegicus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0000034
-
-
Homo sapiens (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
0.000015
-
-
Homo sapiens (2S,4S)-1-[2-(1,1-dimethyl-3-oxo-3-pyrrolidin-1-yl-propylamino)acetyl]-4-fluoro-pyrrolidine-2-carbonitrile
0.000015
-
-
Homo sapiens (2S)-1-[N-[4-(1,3-dihydro-2H-isoindol-2-yl)-2-methyl-4-oxobutan-2-yl]glycyl]pyrrolidine-2-carbonitrile
0.000015
-
-
Homo sapiens N-[(1S,2R)-2-(3-chlorophenyl)cyclopropyl]-3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-3-methylbutanamide
0.000018
-
-
Homo sapiens (2S)-1-[([4-[(3R)-3-hydroxypyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]amino)acetyl]pyrrolidine-2-carbonitrile
0.000018
-
-
Homo sapiens (2S,4S)-1-[N-[4-(3,6-dihydropyridin-1(2H)-yl)-2-methyl-4-oxobutan-2-yl]glycyl]-4-fluoropyrrolidine-2-carbonitrile
0.000019
-
-
Homo sapiens 3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-N-(3,4-dimethoxyphenyl)-3-methylbutanamide
0.000019
-
-
Homo sapiens 3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-3-methyl-N-(pyridin-2-yl)butanamide
0.00002
-
-
Homo sapiens (2S,4S)-4-fluoro-1-[N-[2-methyl-4-(morpholin-4-yl)-4-oxobutan-2-yl]glycyl]pyrrolidine-2-carbonitrile
0.000024
-
-
Homo sapiens (2S,4S)-4-fluoro-1-(N-[4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]glycyl)pyrrolidine-2-carbonitrile
0.000024
-
-
Homo sapiens (2S,4S)-4-fluoro-1-(N-[2-methyl-4-[4-(methylsulfonyl)piperazin-1-yl]-4-oxobutan-2-yl]glycyl)pyrrolidine-2-carbonitrile
0.000026
-
-
Homo sapiens (2S,4S)-4-fluoro-1-[N-[2-methyl-4-oxo-4-(4-oxopiperidin-1-yl)butan-2-yl]glycyl]pyrrolidine-2-carbonitrile
0.000027
-
-
Homo sapiens 3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-N-(3,4-dimethoxyphenyl)-3-methylbutanamide
0.000027
-
-
Homo sapiens (2S,4S)-4-fluoro-1-([[2-methyl-4-oxo-4-(1,3-thiazolidin-3-yl)butan-2-yl]amino]acetyl)pyrrolidine-2-carbonitrile
0.000027
-
-
Homo sapiens (2S,4S)-4-fluoro-1-[N-[2-methyl-4-oxo-4-(piperidin-1-yl)butan-2-yl]glycyl]pyrrolidine-2-carbonitrile
0.000029
-
-
Homo sapiens 3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-N-cyclopentyl-3-methylbutanamide
0.00003
-
-
Homo sapiens (3R)-3-amino-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
0.00003
-
-
Homo sapiens (2S,4S)-4-fluoro-1-[([4-[(3R)-3-hydroxypyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]amino)acetyl]pyrrolidine-2-carbonitrile
0.000032
-
-
Homo sapiens (2S,4S)-4-fluoro-1-(N-[2-methyl-4-[(2R)-2-methylpyrrolidin-1-yl]-4-oxobutan-2-yl]glycyl)pyrrolidine-2-carbonitrile
0.000039
-
-
Homo sapiens (2S,4S)-4-fluoro-1-[([4-[(3R)-3-fluoropyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]amino)acetyl]pyrrolidine-2-carbonitrile
0.00005
-
-
Homo sapiens (2S,4S)-4-fluoro-1-[([4-[(3S)-3-hydroxypyrrolidin-1-yl]-2-methyl-4-oxobutan-2-yl]amino)acetyl]pyrrolidine-2-carbonitrile
0.000051
-
-
Homo sapiens (2S)-1-[[(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile
0.000063
-
-
Homo sapiens ethyl 4-[3-([2-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethyl]amino)-3-methylbutanoyl]piperazine-1-carboxylate
0.000066
-
-
Homo sapiens (2S,4S)-1-[N-[4-(7-azabicyclo[2.2.1]hept-7-yl)-2-methyl-4-oxobutan-2-yl]glycyl]-4-fluoropyrrolidine-2-carbonitrile
0.000071
-
-
Homo sapiens (2S)-1-([[2-methyl-4-oxo-4-(pyrrolidin-1-yl)butan-2-yl]amino]acetyl)pyrrolidine-2-carbonitrile
0.000093
-
-
Homo sapiens (2S,4S)-4-fluoro-1-[N-[2-methyl-4-(4-methylpiperazin-1-yl)-4-oxobutan-2-yl]glycyl]pyrrolidine-2-carbonitrile
0.000116
-
-
Homo sapiens 3-([2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]amino)-N-(3,4-dimethoxyphenyl)-3-methylbutanamide
0.00016
-
-
Homo sapiens (2S,4S)-1-[N-[4-(azepan-1-yl)-2-methyl-4-oxobutan-2-yl]glycyl]-4-fluoropyrrolidine-2-carbonitrile