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Literature summary for 3.4.21.5 extracted from

  • Lu, T.; Markotan, T.; Ballentine, S.K.; Giardino, E.C.; Spurlino, J.; Crysler, C.S.; Brown, K.; Maryanoff, B.E.; Tomczuk, B.E.; Damiano, B.P.; Shukla, U.; End, D.; Andrade-Gordon, P.; Bone, R.F.; Player, M.R.
    Discovery and clinical evaluation of 1-{N-[2-(amidinoaminooxy)ethyl]amino}carbonylmethyl-6-methyl-3-[2,2-difluoro-2-phenylethylamino]pyrazinone (RWJ-671818), a thrombin inhibitor with an oxyguanidine P1 motif (2010), J. Med. Chem., 53, 1843-1856.
    View publication on PubMed

Crystallization (Commentary)

Crystallization (Comment) Organism
alpha-thrombin is crystallized at 4°C in a complex with sulfated hirudin 53-65, sitting drop vapor diffusion method Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
1-[N-[2-(amidino-N'-methylaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(2-[4-methylphenyl]ethylamino)pyrazinone
-
Homo sapiens
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-chloro-3-[2,2-difluoro-2-phenylethylamino]pyrazinone
-
Homo sapiens
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-cyano-3-[2,2-difluoro-2-phenylethylamino]pyrazinone
-
Homo sapiens
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(2,2-diphenylethylamino)pyrazinone
-
Homo sapiens
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(2-[2,4-difluorophenyl]ethylamino)pyrazinone
-
Homo sapiens
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(2-[3,4-difluorophenyl]ethylamino)pyrazinone
-
Homo sapiens
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(2-[4-trifluoromethylphenyl]ethylamino)pyrazinone
-
Homo sapiens
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(2-[5-indanyl]ethylamino)pyrazinone
-
Homo sapiens
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(3,4-dimethoxyphenylethylamino)pyrazinone
-
Homo sapiens
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(4-ethylphenethylamino)pyrazinone
-
Homo sapiens
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(4-fluorophenethylamino)pyrazinone
-
Homo sapiens
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(4-methoxyphenethylamino)pyrazinone
-
Homo sapiens
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-[2,2-difluoro-2-phenylethylamino]pyrazinone RWJ-671818 Homo sapiens
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-[2-(1-naphthalene)ethyl]aminopyrazinone
-
Homo sapiens
argatroban i.e. (2R,4R)-1-[(2S)-5(diaminomethylideneamino)-2-[[(3R)-3-methyl-1,2,3,4-tetrahydroquinolin-8-yl]sulfonylamino]pentanoyl]-4-methyl-piperidine-2-carboxylic acid Homo sapiens
[6-chloro-3-(2,2-difluoro-2-phenyl-ethylamino)-2-oxo-2H-pyrazin-1-yl]acetic acid
-
Homo sapiens

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.32
-
succinyl-AAPR-4-nitroanilide
-
Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
fibrinogen + H2O Homo sapiens
-
fibrin + fibrinopeptide A + fibrinopeptide B
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
fibrinogen + H2O
-
Homo sapiens fibrin + fibrinopeptide A + fibrinopeptide B
-
?
succinyl-AAPR-4-nitroanilide + H2O
-
Homo sapiens succinyl-AAPR + 4-nitroaniline
-
?

Synonyms

Synonyms Comment Organism
alpha-thrombin
-
Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0000013
-
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-[2,2-difluoro-2-phenylethylamino]pyrazinone
-
Homo sapiens
0.0000017
-
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-chloro-3-[2,2-difluoro-2-phenylethylamino]pyrazinone
-
Homo sapiens
0.0000023
-
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-cyano-3-[2,2-difluoro-2-phenylethylamino]pyrazinone
-
Homo sapiens
0.0000068
-
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(2,2-diphenylethylamino)pyrazinone
-
Homo sapiens
0.000011
-
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(4-methoxyphenethylamino)pyrazinone
-
Homo sapiens
0.000012
-
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-[2-(1-naphthalene)ethyl]aminopyrazinone
-
Homo sapiens
0.000013
-
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(4-fluorophenethylamino)pyrazinone
-
Homo sapiens
0.000015
-
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(2-[2,4-difluorophenyl]ethylamino)pyrazinone
-
Homo sapiens
0.000037
-
1-[N-[2-(amidino-N'-methylaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(2-[4-methylphenyl]ethylamino)pyrazinone
-
Homo sapiens
0.000044
-
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(2-[5-indanyl]ethylamino)pyrazinone
-
Homo sapiens
0.000047
-
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(2-[3,4-difluorophenyl]ethylamino)pyrazinone
-
Homo sapiens
0.000047
-
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(2-[4-trifluoromethylphenyl]ethylamino)pyrazinone
-
Homo sapiens
0.000066
-
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(4-ethylphenethylamino)pyrazinone
-
Homo sapiens
0.00012
-
1-[N-[2-(amidinoaminooxy)ethyl]amino]carbonylmethyl-6-methyl-3-(3,4-dimethoxyphenylethylamino)pyrazinone
-
Homo sapiens