Page last updated: 2024-11-08

3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine

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Description

3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine: amiloride prodrug; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID194530
CHEMBL ID290169
SCHEMBL ID11053565
MeSH IDM0085707

Synonyms (14)

Synonym
cgs 4270
73631-29-5
CHEMBL290169 ,
3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloropyrazine-2,6-diamine
cgs-4270
unii-pf467u2v7j
3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole
pf467u2v7j ,
2,6-pyrazinediamine, 3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-
3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine
bdbm50356116
DTXSID90223847
SCHEMBL11053565
FT-0743072
[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)
Urokinase-type plasminogen activatorHomo sapiens (human)IC50 (µMol)1,000.00000.03703.385910.0000AID626488
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (21)

Processvia Protein(s)Taxonomy
positive regulation of cell migrationUrokinase-type plasminogen activatorHomo sapiens (human)
response to hypoxiaUrokinase-type plasminogen activatorHomo sapiens (human)
proteolysisUrokinase-type plasminogen activatorHomo sapiens (human)
chemotaxisUrokinase-type plasminogen activatorHomo sapiens (human)
signal transductionUrokinase-type plasminogen activatorHomo sapiens (human)
blood coagulationUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of signaling receptor activityUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of plasminogen activationUrokinase-type plasminogen activatorHomo sapiens (human)
negative regulation of plasminogen activationUrokinase-type plasminogen activatorHomo sapiens (human)
smooth muscle cell migrationUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of smooth muscle cell migrationUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of cell adhesionUrokinase-type plasminogen activatorHomo sapiens (human)
plasminogen activationUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of cell adhesion mediated by integrinUrokinase-type plasminogen activatorHomo sapiens (human)
urokinase plasminogen activator signaling pathwayUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of cell population proliferationUrokinase-type plasminogen activatorHomo sapiens (human)
fibrinolysisUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of fibrinolysisUrokinase-type plasminogen activatorHomo sapiens (human)
negative regulation of fibrinolysisUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of wound healingUrokinase-type plasminogen activatorHomo sapiens (human)
regulation of smooth muscle cell-matrix adhesionUrokinase-type plasminogen activatorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
serine-type endopeptidase activityUrokinase-type plasminogen activatorHomo sapiens (human)
protein bindingUrokinase-type plasminogen activatorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
extracellular regionUrokinase-type plasminogen activatorHomo sapiens (human)
extracellular spaceUrokinase-type plasminogen activatorHomo sapiens (human)
plasma membraneUrokinase-type plasminogen activatorHomo sapiens (human)
focal adhesionUrokinase-type plasminogen activatorHomo sapiens (human)
external side of plasma membraneUrokinase-type plasminogen activatorHomo sapiens (human)
cell surfaceUrokinase-type plasminogen activatorHomo sapiens (human)
specific granule membraneUrokinase-type plasminogen activatorHomo sapiens (human)
extracellular exosomeUrokinase-type plasminogen activatorHomo sapiens (human)
tertiary granule membraneUrokinase-type plasminogen activatorHomo sapiens (human)
serine protease inhibitor complexUrokinase-type plasminogen activatorHomo sapiens (human)
protein complex involved in cell-matrix adhesionUrokinase-type plasminogen activatorHomo sapiens (human)
serine-type endopeptidase complexUrokinase-type plasminogen activatorHomo sapiens (human)
extracellular spaceUrokinase-type plasminogen activatorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (47)

Assay IDTitleYearJournalArticle
AID18959Compound was tested for diuretic activity against peroral dose of 50 mg/kg in rat1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Synthesis and diuretic profile of 3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine, an amiloride-type diuretic.
AID18962Compound was tested for diuretic activity in urine volume in dogs at a dose of 5 mg/kg1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Synthesis and diuretic profile of 3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine, an amiloride-type diuretic.
AID16171Compound was tested for diuretic activity in sodium content of the 3-h sample was measured by flame photometry in rat1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Synthesis and diuretic profile of 3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine, an amiloride-type diuretic.
AID62812Compound was evaluated for urinary levels (mg) after administration of 0.1 mg/kg at time period 0-24 hr1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175981Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (K+) at a time period of 0-5 hr for dose 9 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175987Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Na+) at a time period of 0-5 hr for dose 3 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175826Compound was evaluated for diuretic activity determined by the ability of to induce electrolytic excretion (Cl-) at a time period of 0-24 hr for dose 3 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID18956Compound was tested for diuretic activity against peroral dose of 100 mg/kg in rat1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Synthesis and diuretic profile of 3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine, an amiloride-type diuretic.
AID16009Compound was tested for diuretic activity in potassium content of the 3-h sample was measured by flame photometry in rat1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Synthesis and diuretic profile of 3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine, an amiloride-type diuretic.
AID175829Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Cl-) at a time period of 0-24 hr for dose 81 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175986Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Na+) at a time period of 0-5 hr for dose 27 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175979Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (K+) at a time period of 0-5 hr for dose 3 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175976Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (K+) at a time period of 0-24 hr for dose 81 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175985Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Na+) at a time period of 0-24 hr for dose 9 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID18958Compound was tested for diuretic activity against peroral dose of 25 mg/kg in rat1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Synthesis and diuretic profile of 3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine, an amiloride-type diuretic.
AID175831Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Cl-) at a time period of 0-5 hr for dose 27 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID16008Compound was tested for diuretic activity in potassium content of the 3-h sample was measured by flame photometry1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Synthesis and diuretic profile of 3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine, an amiloride-type diuretic.
AID626488Inhibition of urokinase-type plasminogen activator2011Bioorganic & medicinal chemistry letters, Nov-15, Volume: 21, Issue:22
Synthesis and preliminary evaluation of amiloride analogs as inhibitors of the urokinase-type plasminogen activator (uPA).
AID175832Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Cl-) at a time period of 0-5 hr for dose 3 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID58592Diuretic activity in mongrel dog was determined by the ability to induce electrolytic excretion (Na+) at a time period of 0-5 hr after administration of 4 mg/kg dose.1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID191506Urine volumes in Sprague-Dawley rats was determined at time period of 0-5 hours dose 3 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175827Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Cl-) at a time period of 0-24 hr for dose 27 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID62813Compound was evaluated for urinary levels (mg) after administration of 0.1 mg/kg at time period 0-6 hr1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175983Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Na+) at a time period of 0-24 hr for dose 3 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175978Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (K+) at a time period of 0-5 hr for dose 27 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID58591Diuretic activity in mongrel dog was determined by the ability to induce electrolytic excretion (K+) at a time period of 0-5 hr after administration of 4 mg/kg dose.1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID18957Compound was tested for diuretic activity against peroral dose of 10 mg/kg in rat1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Synthesis and diuretic profile of 3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine, an amiloride-type diuretic.
AID18960Compound was tested for diuretic activity against peroral dose of 5 mg/kg in rat1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Synthesis and diuretic profile of 3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine, an amiloride-type diuretic.
AID16170Compound was tested for diuretic activity in sodium content of the 3-h sample was measured by flame photometry1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Synthesis and diuretic profile of 3-(3-amino-1,2,4-oxadiazol-5-yl)-5-chloro-2,6-pyrazinediamine, an amiloride-type diuretic.
AID175984Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Na+) at a time period of 0-24 hr for dose 81 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175975Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (K+) at a time period of 0-24 hr for dose 3 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID62814Compound was evaluated for urinary levels (mg) after administration of 0.1 mg/kg at time period 6-24h1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID58404Compound was evaluated for percentage recovery from urine after administration of 0.1 mg/kg dose1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175834Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Cl-) at a time period of 0-5 hr for dose 9 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID58405Compound was evaluated for percentage recovery from urine after administration of 0.3 mg/kg dose1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175988Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Na+) at a time period of 0-5 hr for dose 81 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175989Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Na+) at a time period of 0-5 hr for dose 9 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID58590Diuretic activity in mongrel dog was determined by the ability to induce electrolytic excretion (CL-) at a time period of 0-5 hr after administration of 4 mg/kg dose.1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175835Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (K+) at a time period of 0-24 hr for dose 27 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175980Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (K+) at a time period of 0-5 hr for dose 81 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID191508Urine volumes in Sprague-Dawley rats was determined at time period of 0-5 hours dose 9 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175830Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Cl-) at a time period of 0-24 hr for dose 9 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID191507Urine volumes in Sprague-Dawley rats was determined at time period of 0-5 hours dose 81 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID191505Urine volumes in Sprague-Dawley rats was determined at time period of 0-5 hours dose 27 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175977Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (K+) at a time period of 0-24 hr for dose 9 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175833Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Cl-) at a time period of 0-5 hr for dose 81 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
AID175982Compound was evaluated for diuretic activity determined by the ability to induce electrolytic excretion (Na+) at a time period of 0-24 hr for dose 27 mg/kg1986Journal of medicinal chemistry, Aug, Volume: 29, Issue:8
Synthesis and biological activity of 3-amino-5-(3,5-diamino-6-chloropyrazin-2-yl)-1,2,4-oxadiazole: an amiloride prodrug.
[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-19904 (80.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's1 (20.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.53

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 Index12.53 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.53)

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]