Page last updated: 2024-11-12

f-amidine

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

Description

F-amidine: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11589584
CHEMBL ID1962723
CHEMBL ID1910973
CHEBI ID188065
SCHEMBL ID1979695
MeSH IDM0496777

Synonyms (12)

Synonym
CHEBI:188065
n-[(2s)-1-amino-5-[(1-amino-2-luoroethylidene)amino]-1-oxopentan-2-yl]benzamide
f-amidine
CHEMBL1962723 ,
CHEMBL1910973 ,
bdbm50355658
SCHEMBL1979695
877617-45-3
n-[(2s)-1-amino-5-[(1-amino-2-fluoroethylidene)amino]-1-oxopentan-2-yl]benzamide
(s,z)-n-(1-amino-5-((1-amino-2-fluoroethylidene)amino)-1-oxopentan-2-yl)benzamide
bdbm50581391
AKOS040745786

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Since D-amino amino acids often possess enhanced in cellulo stability, and perhaps unique selectivities, we synthesized a series of D-amino acid analogs of our pan-PAD inhibitor Cl-amidine, hypothesizing that this change would provide inhibitors with enhanced pharmacokinetic properties."( D-amino acid based protein arginine deiminase inhibitors: Synthesis, pharmacokinetics, and in cellulo efficacy.
Anguish, L; Bicker, KL; Cameron, MD; Chumanevich, AA; Chumanevich, AP; Coonrod, SA; Cui, X; Hofseth, LJ; Subramanian, V; Thompson, PR; Witalison, E; Zhang, X, 2012
)
0.38

Bioavailability

ExcerptReferenceRelevance
" The bioavailability of this compound suggests that F-amidine will be a powerful chemical probe of PAD4 function that can be used to dissect the roles of this enzyme in both rheumatoid arthritis and transcriptional control."( A fluoroacetamidine-based inactivator of protein arginine deiminase 4: design, synthesis, and in vitro and in vivo evaluation.
Knuckley, B; Lee, YH; Luo, Y; Stallcup, MR; Thompson, PR, 2006
)
0.58
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-acylglycineAn N-acyl-amino acid in which amino acid specified is glycine.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
cAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)IC50 (µMol)110.80000.00001.068010.0000AID1813072; AID1813073
cAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)IC50 (µMol)110.80000.00001.104010.0000AID1813072; AID1813073
cAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)IC50 (µMol)110.80000.00001.465110.0000AID1813072; AID1813073
cAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)IC50 (µMol)110.80000.00001.146310.0000AID1813072; AID1813073
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (30)

Processvia Protein(s)Taxonomy
cAMP catabolic processcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
signal transductioncAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
G protein-coupled receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
sensory perception of smellcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
regulation of protein kinase A signalingcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
cellular response to xenobiotic stimuluscAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
regulation of adenylate cyclase-activating G protein-coupled receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
cAMP-mediated signalingcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
neutrophil homeostasiscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cAMP catabolic processcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
neutrophil chemotaxiscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
positive regulation of type II interferon productioncAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
positive regulation of interleukin-2 productioncAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
T cell receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
leukocyte migrationcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cellular response to lipopolysaccharidecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cellular response to xenobiotic stimuluscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cellular response to epinephrine stimuluscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
negative regulation of adenylate cyclase-activating adrenergic receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
regulation of cardiac muscle cell contractioncAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
negative regulation of relaxation of cardiac musclecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
regulation of calcium ion transmembrane transport via high voltage-gated calcium channelcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cAMP-mediated signalingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cAMP catabolic processcAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
cAMP-mediated signalingcAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
regulation of heart ratecAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
cAMP catabolic processcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
positive regulation of heart ratecAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
regulation of release of sequestered calcium ion into cytosol by sarcoplasmic reticulumcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
positive regulation of type II interferon productioncAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
positive regulation of interleukin-2 productioncAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
positive regulation of interleukin-5 productioncAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
negative regulation of peptidyl-serine phosphorylationcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
negative regulation of heart contractioncAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
T cell receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
establishment of endothelial barriercAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
adrenergic receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
regulation of cardiac muscle cell contractioncAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
negative regulation of adenylate cyclase-activating G protein-coupled receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
regulation of cell communication by electrical coupling involved in cardiac conductioncAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
negative regulation of relaxation of cardiac musclecAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
regulation of calcium ion transmembrane transport via high voltage-gated calcium channelcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
cAMP-mediated signalingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
3',5'-cyclic-AMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
protein bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
cAMP bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
metal ion bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
calcium channel regulator activitycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
protein bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cAMP bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
gamma-tubulin bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
transmembrane transporter bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
metal ion bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
metal ion bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
3',5'-cyclic-nucleotide phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
calcium channel regulator activitycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
protein bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
enzyme bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
signaling receptor regulator activitycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
cAMP bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
beta-2 adrenergic receptor bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
transmembrane transporter bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
metal ion bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
ATPase bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
scaffold protein bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
heterocyclic compound bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (19)

Processvia Protein(s)Taxonomy
nucleoplasmcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
plasma membranecAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
membranecAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
ruffle membranecAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
perinuclear region of cytoplasmcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
perinuclear region of cytoplasmcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
nucleuscAMP-specific 3',5'-cyclic phosphodiesterase 4AHomo sapiens (human)
centrosomecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
synaptic vesiclecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
postsynaptic densitycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
Z disccAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
dendritic spinecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
excitatory synapsecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
gamma-tubulin complexcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
voltage-gated calcium channel complexcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
nucleuscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
perinuclear region of cytoplasmcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
extracellular spacecAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
ciliumcAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
nucleuscAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
perinuclear region of cytoplasmcAMP-specific 3',5'-cyclic phosphodiesterase 4CHomo sapiens (human)
centrosomecAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
plasma membranecAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
apical plasma membranecAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
voltage-gated calcium channel complexcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
calcium channel complexcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
nucleuscAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
perinuclear region of cytoplasmcAMP-specific 3',5'-cyclic phosphodiesterase 4DHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID1364667Ratio of Kinact to Ki for recombinant His6-tagged PAD3 (unknown origin) preincubated for 10 mins followed by BAA substrate addition measured after 15 mins by COLDER assay2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
Development of a Selective Inhibitor of Protein Arginine Deiminase 2.
AID712879Ratio of Kinact to Ki for PAD12012ACS medicinal chemistry letters, Oct-26, Volume: 3, Issue:12
D-amino acid based protein arginine deiminase inhibitors: Synthesis, pharmacokinetics, and in cellulo efficacy.
AID1196525Inhibition of PAD4 (unknown origin) using N-alpha-benzoyl-L-arginine ethyl ester as substrate assessed as citrulline production after 15 mins by COLDER assay2015Journal of medicinal chemistry, Feb-12, Volume: 58, Issue:3
Design, synthesis, and biological evaluation of tetrazole analogs of Cl-amidine as protein arginine deiminase inhibitors.
AID712874Selectivity ratio of Kinact to Ki for PAD1 to Kinact to Ki for PAD42012ACS medicinal chemistry letters, Oct-26, Volume: 3, Issue:12
D-amino acid based protein arginine deiminase inhibitors: Synthesis, pharmacokinetics, and in cellulo efficacy.
AID1364666Ratio of Kinact to Ki for recombinant human PAD2 expressed in Escherichia coli BL21(DE3)pLysS cells preincubated for 10 mins followed by BAEE substrate addition measured after 15 mins by COLDER assay2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
Development of a Selective Inhibitor of Protein Arginine Deiminase 2.
AID712877Selectivity ratio of Kinact to Ki for PAD1 to Kinact to Ki for PAD22012ACS medicinal chemistry letters, Oct-26, Volume: 3, Issue:12
D-amino acid based protein arginine deiminase inhibitors: Synthesis, pharmacokinetics, and in cellulo efficacy.
AID1196527Ratio of Kinact to Ki for PAD2 (unknown origin) using N-alpha-benzoyl-L-arginine ethyl ester as substrate assessed as citrulline production after 15 mins by COLDER assay2015Journal of medicinal chemistry, Feb-12, Volume: 58, Issue:3
Design, synthesis, and biological evaluation of tetrazole analogs of Cl-amidine as protein arginine deiminase inhibitors.
AID1364668Ratio of Kinact to Ki for recombinant full length N-terminal GST-tagged human PAD4 expressed in Escherichia coli Rosetta cells preincubated for 10 mins followed by BAEE substrate addition measured after 15 mins by COLDER assay2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
Development of a Selective Inhibitor of Protein Arginine Deiminase 2.
AID712876Ratio of Kinact to Ki for PAD42012ACS medicinal chemistry letters, Oct-26, Volume: 3, Issue:12
D-amino acid based protein arginine deiminase inhibitors: Synthesis, pharmacokinetics, and in cellulo efficacy.
AID712878Ratio of Kinact to Ki for PAD32012ACS medicinal chemistry letters, Oct-26, Volume: 3, Issue:12
D-amino acid based protein arginine deiminase inhibitors: Synthesis, pharmacokinetics, and in cellulo efficacy.
AID1813073Inhibition of PDE4 (unknown origin) in absence of calcium by colorimetric assay2021European journal of medicinal chemistry, Dec-15, Volume: 226Peptidylarginine deiminases 4 as a promising target in drug discovery.
AID712875Selectivity ratio of Kinact to Ki for PAD1 to Kinact to Ki for PAD32012ACS medicinal chemistry letters, Oct-26, Volume: 3, Issue:12
D-amino acid based protein arginine deiminase inhibitors: Synthesis, pharmacokinetics, and in cellulo efficacy.
AID1364665Ratio of Kinact to Ki for recombinant His6-tagged PAD1 (unknown origin) preincubated for 10 mins followed by BAEE substrate addition measured after 15 mins by COLDER assay2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
Development of a Selective Inhibitor of Protein Arginine Deiminase 2.
AID1813072Inhibition of PDE4 (unknown origin) in presence of calcium by colorimetric assay2021European journal of medicinal chemistry, Dec-15, Volume: 226Peptidylarginine deiminases 4 as a promising target in drug discovery.
AID712880Ratio of Kinact to Ki for PAD22012ACS medicinal chemistry letters, Oct-26, Volume: 3, Issue:12
D-amino acid based protein arginine deiminase inhibitors: Synthesis, pharmacokinetics, and in cellulo efficacy.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (25.00)29.6817
2010's5 (62.50)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.68

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 Index12.68 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.88 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.68)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]