Page last updated: 2024-11-13

n-(carbamoylmethyl)-3-trifluoromethyl benzamido-4-chlorobenzyl 3-aminopyrrolidine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID44453327
CHEMBL ID255408
MeSH IDM0536497

Synonyms (16)

Synonym
CHEMBL255408 ,
bdbm50236430
(r)-n-(2-(1-(4-chlorobenzyl)pyrrolidin-3-ylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide
teijin compound 1
CS-7875
NCGC00370812-01
HY-108323
ccr2 antagonist 4
226226-39-7
teijin-compound-1
n-[2-[[(3r)-1-[(4-chlorophenyl)methyl]-3-pyrrolidinyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamidehydrochloride
n-[2-[[(3r)-1-[(4-chlorophenyl)methyl]pyrrolidin-3-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide
MS-27904
BJA22639
baoqjsulmwxfrk-gosisdbhsa-n
AKOS040740191

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
cytochrome P450 family 3 subfamily A polypeptide 4Homo sapiens (human)Potency9.52210.01237.983543.2770AID1645841
GVesicular stomatitis virusPotency8.48660.01238.964839.8107AID1645842
cytochrome P450 2D6Homo sapiens (human)Potency0.05350.00108.379861.1304AID1645840
Interferon betaHomo sapiens (human)Potency8.48660.00339.158239.8107AID1645842
HLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)Potency8.48660.01238.964839.8107AID1645842
Inositol hexakisphosphate kinase 1Homo sapiens (human)Potency8.48660.01238.964839.8107AID1645842
cytochrome P450 2C9, partialHomo sapiens (human)Potency8.48660.01238.964839.8107AID1645842
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
C-C chemokine receptor type 2Homo sapiens (human)IC50 (µMol)0.81070.00000.67366.6990AID241076; AID325950; AID325951; AID473572; AID473574; AID473576
[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)
C-C chemokine receptor type 2Homo sapiens (human)EC50 (µMol)0.02000.02000.02000.0200AID246400
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (95)

Processvia Protein(s)Taxonomy
cell surface receptor signaling pathway via JAK-STATInterferon betaHomo sapiens (human)
response to exogenous dsRNAInterferon betaHomo sapiens (human)
B cell activation involved in immune responseInterferon betaHomo sapiens (human)
cell surface receptor signaling pathwayInterferon betaHomo sapiens (human)
cell surface receptor signaling pathway via JAK-STATInterferon betaHomo sapiens (human)
response to virusInterferon betaHomo sapiens (human)
positive regulation of autophagyInterferon betaHomo sapiens (human)
cytokine-mediated signaling pathwayInterferon betaHomo sapiens (human)
natural killer cell activationInterferon betaHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylation of STAT proteinInterferon betaHomo sapiens (human)
cellular response to interferon-betaInterferon betaHomo sapiens (human)
B cell proliferationInterferon betaHomo sapiens (human)
negative regulation of viral genome replicationInterferon betaHomo sapiens (human)
innate immune responseInterferon betaHomo sapiens (human)
positive regulation of innate immune responseInterferon betaHomo sapiens (human)
regulation of MHC class I biosynthetic processInterferon betaHomo sapiens (human)
negative regulation of T cell differentiationInterferon betaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIInterferon betaHomo sapiens (human)
defense response to virusInterferon betaHomo sapiens (human)
type I interferon-mediated signaling pathwayInterferon betaHomo sapiens (human)
neuron cellular homeostasisInterferon betaHomo sapiens (human)
cellular response to exogenous dsRNAInterferon betaHomo sapiens (human)
cellular response to virusInterferon betaHomo sapiens (human)
negative regulation of Lewy body formationInterferon betaHomo sapiens (human)
negative regulation of T-helper 2 cell cytokine productionInterferon betaHomo sapiens (human)
positive regulation of apoptotic signaling pathwayInterferon betaHomo sapiens (human)
response to exogenous dsRNAInterferon betaHomo sapiens (human)
B cell differentiationInterferon betaHomo sapiens (human)
natural killer cell activation involved in immune responseInterferon betaHomo sapiens (human)
adaptive immune responseInterferon betaHomo sapiens (human)
T cell activation involved in immune responseInterferon betaHomo sapiens (human)
humoral immune responseInterferon betaHomo sapiens (human)
positive regulation of T cell mediated cytotoxicityHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
adaptive immune responseHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
antigen processing and presentation of endogenous peptide antigen via MHC class I via ER pathway, TAP-independentHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
regulation of T cell anergyHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
defense responseHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
immune responseHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
detection of bacteriumHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
regulation of interleukin-12 productionHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
regulation of interleukin-6 productionHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
protection from natural killer cell mediated cytotoxicityHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
innate immune responseHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
regulation of dendritic cell differentiationHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
antigen processing and presentation of endogenous peptide antigen via MHC class IbHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
cytokine-mediated signaling pathwayC-C chemokine receptor type 2Homo sapiens (human)
blood vessel remodelingC-C chemokine receptor type 2Homo sapiens (human)
dendritic cell chemotaxisC-C chemokine receptor type 2Homo sapiens (human)
monocyte chemotaxisC-C chemokine receptor type 2Homo sapiens (human)
regulation of T cell cytokine productionC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of T-helper 1 type immune responseC-C chemokine receptor type 2Homo sapiens (human)
negative regulation of type 2 immune responseC-C chemokine receptor type 2Homo sapiens (human)
intracellular calcium ion homeostasisC-C chemokine receptor type 2Homo sapiens (human)
chemotaxisC-C chemokine receptor type 2Homo sapiens (human)
humoral immune responseC-C chemokine receptor type 2Homo sapiens (human)
cellular defense responseC-C chemokine receptor type 2Homo sapiens (human)
negative regulation of adenylate cyclase activityC-C chemokine receptor type 2Homo sapiens (human)
cell surface receptor signaling pathway via JAK-STATC-C chemokine receptor type 2Homo sapiens (human)
response to woundingC-C chemokine receptor type 2Homo sapiens (human)
regulation of vascular endothelial growth factor productionC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of T cell chemotaxisC-C chemokine receptor type 2Homo sapiens (human)
negative regulation of angiogenesisC-C chemokine receptor type 2Homo sapiens (human)
sensory perception of painC-C chemokine receptor type 2Homo sapiens (human)
cellular homeostasisC-C chemokine receptor type 2Homo sapiens (human)
hemopoiesisC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of type II interferon productionC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of interleukin-2 productionC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of tumor necrosis factor productionC-C chemokine receptor type 2Homo sapiens (human)
monocyte extravasationC-C chemokine receptor type 2Homo sapiens (human)
T-helper 17 cell chemotaxisC-C chemokine receptor type 2Homo sapiens (human)
negative regulation of eosinophil degranulationC-C chemokine receptor type 2Homo sapiens (human)
regulation of T cell differentiationC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of alpha-beta T cell proliferationC-C chemokine receptor type 2Homo sapiens (human)
homeostasis of number of cells within a tissueC-C chemokine receptor type 2Homo sapiens (human)
regulation of inflammatory responseC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of inflammatory responseC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of T cell activationC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of synaptic transmission, glutamatergicC-C chemokine receptor type 2Homo sapiens (human)
leukocyte adhesion to vascular endothelial cellC-C chemokine receptor type 2Homo sapiens (human)
chemokine-mediated signaling pathwayC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of monocyte chemotaxisC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of immune complex clearance by monocytes and macrophagesC-C chemokine receptor type 2Homo sapiens (human)
inflammatory response to woundingC-C chemokine receptor type 2Homo sapiens (human)
neutrophil clearanceC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of cold-induced thermogenesisC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of leukocyte tethering or rollingC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of NMDA glutamate receptor activityC-C chemokine receptor type 2Homo sapiens (human)
macrophage migrationC-C chemokine receptor type 2Homo sapiens (human)
regulation of macrophage migrationC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of thymocyte migrationC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of monocyte extravasationC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of CD8-positive, alpha-beta T cell extravasationC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of astrocyte chemotaxisC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of hematopoietic stem cell migrationC-C chemokine receptor type 2Homo sapiens (human)
cell chemotaxisC-C chemokine receptor type 2Homo sapiens (human)
calcium-mediated signalingC-C chemokine receptor type 2Homo sapiens (human)
inflammatory responseC-C chemokine receptor type 2Homo sapiens (human)
immune responseC-C chemokine receptor type 2Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationC-C chemokine receptor type 2Homo sapiens (human)
inositol phosphate metabolic processInositol hexakisphosphate kinase 1Homo sapiens (human)
phosphatidylinositol phosphate biosynthetic processInositol hexakisphosphate kinase 1Homo sapiens (human)
negative regulation of cold-induced thermogenesisInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol phosphate biosynthetic processInositol hexakisphosphate kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (26)

Processvia Protein(s)Taxonomy
cytokine activityInterferon betaHomo sapiens (human)
cytokine receptor bindingInterferon betaHomo sapiens (human)
type I interferon receptor bindingInterferon betaHomo sapiens (human)
protein bindingInterferon betaHomo sapiens (human)
chloramphenicol O-acetyltransferase activityInterferon betaHomo sapiens (human)
TAP bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
signaling receptor bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
protein bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
peptide antigen bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
TAP bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
protein-folding chaperone bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
chemokine receptor activityC-C chemokine receptor type 2Homo sapiens (human)
protein bindingC-C chemokine receptor type 2Homo sapiens (human)
CCR2 chemokine receptor bindingC-C chemokine receptor type 2Homo sapiens (human)
chemokine (C-C motif) ligand 2 bindingC-C chemokine receptor type 2Homo sapiens (human)
chemokine (C-C motif) ligand 12 bindingC-C chemokine receptor type 2Homo sapiens (human)
chemokine (C-C motif) ligand 7 bindingC-C chemokine receptor type 2Homo sapiens (human)
identical protein bindingC-C chemokine receptor type 2Homo sapiens (human)
C-C chemokine bindingC-C chemokine receptor type 2Homo sapiens (human)
C-C chemokine receptor activityC-C chemokine receptor type 2Homo sapiens (human)
inositol-1,3,4,5,6-pentakisphosphate kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol hexakisphosphate kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol heptakisphosphate kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol hexakisphosphate 5-kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
protein bindingInositol hexakisphosphate kinase 1Homo sapiens (human)
ATP bindingInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol hexakisphosphate 1-kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol hexakisphosphate 3-kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol 5-diphosphate pentakisphosphate 5-kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol diphosphate tetrakisphosphate kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (26)

Processvia Protein(s)Taxonomy
extracellular spaceInterferon betaHomo sapiens (human)
extracellular regionInterferon betaHomo sapiens (human)
Golgi membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
endoplasmic reticulumHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
Golgi apparatusHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
plasma membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
cell surfaceHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
ER to Golgi transport vesicle membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
secretory granule membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
phagocytic vesicle membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
early endosome membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
recycling endosome membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
extracellular exosomeHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
lumenal side of endoplasmic reticulum membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
MHC class I protein complexHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
extracellular spaceHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
external side of plasma membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
fibrillar centerC-C chemokine receptor type 2Homo sapiens (human)
cytoplasmC-C chemokine receptor type 2Homo sapiens (human)
cytosolC-C chemokine receptor type 2Homo sapiens (human)
plasma membraneC-C chemokine receptor type 2Homo sapiens (human)
membraneC-C chemokine receptor type 2Homo sapiens (human)
dendriteC-C chemokine receptor type 2Homo sapiens (human)
neuronal cell bodyC-C chemokine receptor type 2Homo sapiens (human)
perikaryonC-C chemokine receptor type 2Homo sapiens (human)
perinuclear region of cytoplasmC-C chemokine receptor type 2Homo sapiens (human)
cytoplasmC-C chemokine receptor type 2Homo sapiens (human)
external side of plasma membraneC-C chemokine receptor type 2Homo sapiens (human)
fibrillar centerInositol hexakisphosphate kinase 1Homo sapiens (human)
nucleoplasmInositol hexakisphosphate kinase 1Homo sapiens (human)
cytosolInositol hexakisphosphate kinase 1Homo sapiens (human)
nucleusInositol hexakisphosphate kinase 1Homo sapiens (human)
cytoplasmInositol hexakisphosphate kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID241076Concentration required to inhibit [125I]MCP-1 binding to Chemokine receptor 2B2004Bioorganic & medicinal chemistry letters, Nov-01, Volume: 14, Issue:21
Small molecule antagonists of the CCR2b receptor. Part 2: Discovery process and initial structure-activity relationships of diamine derivatives.
AID243504Inhibition of [125I]MCP-1 binding to Chemokine receptor 2B at 10 uM2004Bioorganic & medicinal chemistry letters, Nov-01, Volume: 14, Issue:21
Small molecule antagonists of the CCR2b receptor. Part 2: Discovery process and initial structure-activity relationships of diamine derivatives.
AID246400Inhibition of MCP-1 induced chemotaxis in THP-1 cells2004Bioorganic & medicinal chemistry letters, Nov-01, Volume: 14, Issue:21
Small molecule antagonists of the CCR2b receptor. Part 2: Discovery process and initial structure-activity relationships of diamine derivatives.
AID473576Antagonist activity at CCR2 in human THP1 cells assessed as inhibition of MCP1-induced chemotaxis after 1 hr by crystal violet staining2010Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7
Synthesis and biological evaluation of 3-aminopyrrolidine derivatives as CC chemokine receptor 2 antagonists.
AID473572Displacement of [125I]MCP1 from human CCR2B receptor expressed in HEK293-EBNA cells2010Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7
Synthesis and biological evaluation of 3-aminopyrrolidine derivatives as CC chemokine receptor 2 antagonists.
AID325951Antagonist activity at human CCR2 in THP1 cells assessed as inhibition of MCP1-induced chemotaxis2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Potent antagonists of the CCR2b receptor. Part 3: SAR of the (R)-3-aminopyrrolidine series.
AID325950Displacement of [125I]MCP1 from human CCR2b in THP1 cells2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Potent antagonists of the CCR2b receptor. Part 3: SAR of the (R)-3-aminopyrrolidine series.
AID473574Antagonist activity at human CCR2B receptor expressed in HEK293 cells assessed as inhibition of MCP1-induced increase in intracellular calcium level2010Bioorganic & medicinal chemistry letters, Apr-01, Volume: 20, Issue:7
Synthesis and biological evaluation of 3-aminopyrrolidine derivatives as CC chemokine receptor 2 antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (33.33)29.6817
2010's2 (33.33)24.3611
2020's2 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.56

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.56 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]