Compounds > prn694
Page last updated: 2024-11-13

prn694

Description

PRN694: an inhibitor of both interleukin-2-inducible T-cell kinase and resting lymphocyte kinase; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID90044055
CHEMBL ID4541397
SCHEMBL ID15574136
SCHEMBL ID20767489
MeSH IDM000605563

Synonyms (24)

Synonym
SCHEMBL15574136
gtpl9285
5-(difluoromethyl)-n-[5-[[[(2s)-3,3-dimethylbutan-2-yl]amino]methyl]-1-[[(2r)-1-prop-2-enoylpyrrolidin-2-yl]methyl]benzimidazol-2-yl]thiophene-2-carboxamide
k5iz54df9g ,
2-thiophenecarboxamide, 5-(difluoromethyl)-n-(1-(((2r)-1-(1-oxo-2-propen-1-yl)-2-pyrrolidinyl)methyl)-5-((((1s)-1,2,2-trimethylpropyl)amino)methyl)-1h-benzimidazol-2-yl)-
unii-k5iz54df9g
5-(difluoromethyl)-n-(5-((((2s)-3,3-dimethylbutan-2-yl)amino)methyl)-1-(((2r)-1-prop-2-enoylpyrrolidin-2-yl)methyl)benzimidazol-2-yl)thiophene-2-carboxamide
5-(difluoromethyl)-n-(1-(((2r)-1-(1-oxo-2-propen-1-yl)-2-pyrrolidinyl)methyl)-5-((((1s)-1,2,2-trimethylpropyl)amino)methyl)-1h-benzimidazol-2-yl)-2-thiophenecarboxamide
(e)-n-(1-(((r)-1-acryloylpyrrolidin-2-yl)methyl)-5-((((s)-3,3-dimethylbutan-2-yl)amino)methyl)-1h-benzo[d]imidazol-2(3h)-ylidene)-5-(difluoromethyl)thiophene-2-carboxamide
prn694
1575818-46-0
CS-0012239
5-(difluoromethyl)-n-[1-[[(2r)-1-(1-oxo-2-propen-1-yl)-2-pyrrolidinyl]methyl]-5-[[[(1s)-1,2,2-trimethylpropyl]amino]methyl]-1h-benzimidazol-2-yl]-2-thiophenecarboxamide
mfcd28963888
HY-12680
SCHEMBL20767489
bdbm290224
us9573958, compound 59
n-(1-(((r)-1-acryloylpyrrolidin-2-yl)methyl)-5-((((s)-3,3-dimethylbutan-2-yl)amino)methyl)-1h-benzo[d]imidazol-2-yl)-5-(difluoromethyl)thiophene-2-carboxamide
MS-29999
CHEMBL4541397 ,
bdbm50537959
nxtkfbgdldpflb-pkobyxmfsa-n
AKOS040742449
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Tyrosine-protein kinase ITK/TSKHomo sapiens (human)IC50 (µMol)0.00320.00100.30905.6500AID1646927
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Tyrosine-protein kinase ITK/TSKHomo sapiens (human)EC50 (µMol)0.15700.15700.15700.1570AID1646972
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (12)

Processvia Protein(s)Taxonomy
positive regulation of cytokine productionTyrosine-protein kinase ITK/TSKHomo sapiens (human)
adaptive immune responseTyrosine-protein kinase ITK/TSKHomo sapiens (human)
cellular defense responseTyrosine-protein kinase ITK/TSKHomo sapiens (human)
signal transductionTyrosine-protein kinase ITK/TSKHomo sapiens (human)
activation of phospholipase C activityTyrosine-protein kinase ITK/TSKHomo sapiens (human)
intracellular signal transductionTyrosine-protein kinase ITK/TSKHomo sapiens (human)
T cell activationTyrosine-protein kinase ITK/TSKHomo sapiens (human)
gamma-delta T cell activationTyrosine-protein kinase ITK/TSKHomo sapiens (human)
T cell receptor signaling pathwayTyrosine-protein kinase ITK/TSKHomo sapiens (human)
protein phosphorylationTyrosine-protein kinase ITK/TSKHomo sapiens (human)
B cell receptor signaling pathwayTyrosine-protein kinase ITK/TSKHomo sapiens (human)
NK T cell differentiationTyrosine-protein kinase ITK/TSKHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
non-membrane spanning protein tyrosine kinase activityTyrosine-protein kinase ITK/TSKHomo sapiens (human)
protein bindingTyrosine-protein kinase ITK/TSKHomo sapiens (human)
ATP bindingTyrosine-protein kinase ITK/TSKHomo sapiens (human)
metal ion bindingTyrosine-protein kinase ITK/TSKHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleusTyrosine-protein kinase ITK/TSKHomo sapiens (human)
cytosolTyrosine-protein kinase ITK/TSKHomo sapiens (human)
cell-cell junctionTyrosine-protein kinase ITK/TSKHomo sapiens (human)
plasma membraneTyrosine-protein kinase ITK/TSKHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1551683Inhibition of 1-(4-((2-((4-(4-(but-3-yn-1-yl)piperazin-1-yl)phenyl)amino)-5-(6-(methylamino)pyrazin-2-yl)-7H-pyrrolo [2,3-d]pyrimidin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one probe binding to ITK in human Jurkat cells at 10 uM preincubated for 3 hrs follow2019European journal of medicinal chemistry, Jul-01, Volume: 173Discovery of 7H-pyrrolo[2,3-d]pyrimidine derivatives as selective covalent irreversible inhibitors of interleukin-2-inducible T-cell kinase (Itk).
AID1646931Irreversible inhibition of binding of N-(2-((6-((but-3-yn-1-yloxy) (phenyl)methyl)-2-(6-(difluoromethyl)-1H-indazol-3-yl)-1H-indol-4-yl)oxy)ethyl)acrylamide to recombinant ITK (unknown origin) at 50 uM pretreated with compound prior to probe addition by f2020European journal of medicinal chemistry, Feb-01, Volume: 187Design, synthesis and structure-activity relationship of indolylindazoles as potent and selective covalent inhibitors of interleukin-2 inducible T-cell kinase (ITK).
AID1646975Irreversible inhibition of ITK in anti-CD3/CD28 beads-stimulated human Jurkat cells assessed as reduction in Plcgamma1 phosphorylation at 3 uM incubated for 2 hrs followed by compound washout with PBS and later stimulated with antiCD3/CD28 for 15 mins by 2020European journal of medicinal chemistry, Feb-01, Volume: 187Design, synthesis and structure-activity relationship of indolylindazoles as potent and selective covalent inhibitors of interleukin-2 inducible T-cell kinase (ITK).
AID1646972Inhibition of ITK in anti-CD3/CD28 beads-stimulated human Jurkat cells assessed as reduction in Plcgamma1 phosphorylation incubated for 2 hrs followed by stimulation with anti-CD3/CD28 beads by Western blot analysis2020European journal of medicinal chemistry, Feb-01, Volume: 187Design, synthesis and structure-activity relationship of indolylindazoles as potent and selective covalent inhibitors of interleukin-2 inducible T-cell kinase (ITK).
AID1646927Inhibition of ITK (unknown origin)2020European journal of medicinal chemistry, Feb-01, Volume: 187Design, synthesis and structure-activity relationship of indolylindazoles as potent and selective covalent inhibitors of interleukin-2 inducible T-cell kinase (ITK).
AID1551633Irreversible inhibition of 1-(4-((2-((4-(4-(but-3-yn-1-yl)piperazin-1-yl)phenyl)amino)-5-(6-(methylamino)pyrazin-2-yl)-7H-pyrrolo [2,3-d]pyrimidin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one probe binding to recombinant human ITK at 20 uM preincubated for 2 h2019European journal of medicinal chemistry, Jul-01, Volume: 173Discovery of 7H-pyrrolo[2,3-d]pyrimidine derivatives as selective covalent irreversible inhibitors of interleukin-2-inducible T-cell kinase (Itk).
AID1345664Human BMX non-receptor tyrosine kinase (Tec family)2015The Journal of biological chemistry, Mar-06, Volume: 290, Issue:10
Targeting interleukin-2-inducible T-cell kinase (ITK) and resting lymphocyte kinase (RLK) using a novel covalent inhibitor PRN694.
AID1345682Human BLK proto-oncogene, Src family tyrosine kinase (Src family)2015The Journal of biological chemistry, Mar-06, Volume: 290, Issue:10
Targeting interleukin-2-inducible T-cell kinase (ITK) and resting lymphocyte kinase (RLK) using a novel covalent inhibitor PRN694.
AID1345860Human TXK tyrosine kinase (Tec family)2015The Journal of biological chemistry, Mar-06, Volume: 290, Issue:10
Targeting interleukin-2-inducible T-cell kinase (ITK) and resting lymphocyte kinase (RLK) using a novel covalent inhibitor PRN694.
AID1345617Human Bruton tyrosine kinase (Tec family)2015The Journal of biological chemistry, Mar-06, Volume: 290, Issue:10
Targeting interleukin-2-inducible T-cell kinase (ITK) and resting lymphocyte kinase (RLK) using a novel covalent inhibitor PRN694.
AID1345744Human Janus kinase 3 (Janus kinase (JakA) family)2015The Journal of biological chemistry, Mar-06, Volume: 290, Issue:10
Targeting interleukin-2-inducible T-cell kinase (ITK) and resting lymphocyte kinase (RLK) using a novel covalent inhibitor PRN694.
AID1345882Human tec protein tyrosine kinase (Tec family)2015The Journal of biological chemistry, Mar-06, Volume: 290, Issue:10
Targeting interleukin-2-inducible T-cell kinase (ITK) and resting lymphocyte kinase (RLK) using a novel covalent inhibitor PRN694.
AID1345705Human IL2 inducible T cell kinase (Tec family)2015The Journal of biological chemistry, Mar-06, Volume: 290, Issue:10
Targeting interleukin-2-inducible T-cell kinase (ITK) and resting lymphocyte kinase (RLK) using a novel covalent inhibitor PRN694.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's4 (80.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.35

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index20.35 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.35)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
methotrexate
[no description available]		2.1710dicarboxylic acid;
monocarboxylic acid amide;
pteridines		abortifacient;
antimetabolite;
antineoplastic agent;
antirheumatic drug;
dermatologic drug;
DNA synthesis inhibitor;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
immunosuppressive agent
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		2.1110cysteiniumfundamental metabolite
N-[5-[[5-[(4-acetyl-1-piperazinyl)-oxomethyl]-4-methoxy-2-methylphenyl]thio]-2-thiazolyl]-4-[(3,3-dimethylbutan-2-ylamino)methyl]benzamide
[no description available]		2.2510benzamides
ConditionIndicatedRelationship StrengthStudiesTrials
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.1710
Palmoplantaris Pustulosis
[description not available]		02.5820
Psoriasis
A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.		07.5820
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