Page last updated: 2024-12-06

bufrolin

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

Description

bufrolin: inhibits the release of histamine; proposed for treatment of hay fever, asthma and skin allergies; minor descriptor (79-86); on line & INDEX MEDICUS search PHENANTHROLINES (79-86); RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID72103
CHEMBL ID150764
SCHEMBL ID2109492
MeSH IDM0263136

Synonyms (27)

Synonym
ici-74917
bufrolin
CHEMBL150764 ,
6-butyl-4,10-dioxo-1,7-dihydro-1,7-phenanthroline-2,8-dicarboxylic acid
54867-56-0
6-butyl-4,10-dioxo-1,4,7,10-tetrahydro-[1,7]phenanthroline-2,8-dicarboxylic acid(bufrolin)
bdbm50020876
6-butyl-4,10-dioxo-1,4,7,10-tetrahydro-[1,7]phenanthroline-2,8-dicarboxylic acid
6-butyl-1,4,7,10-tetrahydro-4,10-dioxo-1,7-phenanthroline-2,8-dicarboxylic acid
bufroline [inn-french]
6-butyl-1,4,7,10-tetrahydro-4,10-dioxo-1,7-phenanthroline-2,8-dicarbonsaeure
bufrolinum
bufrolinum [inn-latin]
bufroline
bufrolino
unii-46c1px266n
46c1px266n ,
bufrolino [inn-spanish]
bufrolin [inn:ban]
bufrolin [mart.]
bufrolin [inn]
SCHEMBL2109492
DTXSID60203353
Q27258923
CS-0025896
HY-106481
AT38170
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
cGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)IC50 (µMol)80.00000.00001.77679.2000AID158293
Alkaline phosphatase, germ cell typeHomo sapiens (human)IC50 (µMol)1,595.00000.60000.90001.2000AID32834; AID32835
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AHomo sapiens (human)IC50 (µMol)16.00000.23002.510510.0000AID158892
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)IC50 (µMol)16.00000.00002.14179.2000AID158892
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CHomo sapiens (human)IC50 (µMol)16.00000.23001.98149.0000AID158892
[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)
G-protein coupled receptor 35Homo sapiens (human)EC50 (µMol)0.01300.00202.50079.8000AID1775491
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (43)

Processvia Protein(s)Taxonomy
heart valve developmentcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
ventricular septum developmentcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
aorta developmentcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwaycGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
regulation of cGMP-mediated signalingcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cAMP-mediated signalingcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cGMP-mediated signalingcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cellular response to macrophage colony-stimulating factor stimuluscGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
negative regulation of vascular permeabilitycGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
positive regulation of vascular permeabilitycGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
regulation of cAMP-mediated signalingcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cGMP catabolic processcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
positive regulation of inflammatory responsecGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
establishment of endothelial barriercGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cellular response to mechanical stimuluscGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cellular response to cAMPcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cellular response to cGMPcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cellular response to transforming growth factor beta stimuluscGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
negative regulation of adenylate cyclase-activating G protein-coupled receptor signaling pathwaycGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cellular response to 2,3,7,8-tetrachlorodibenzodioxinecGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
positive regulation of gene expressioncGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
negative regulation of cGMP-mediated signalingcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
negative regulation of cAMP-mediated signalingcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
regulation of mitochondrion organizationcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
dephosphorylationAlkaline phosphatase, germ cell typeHomo sapiens (human)
regulation of smooth muscle cell apoptotic processCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AHomo sapiens (human)
cGMP catabolic processCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AHomo sapiens (human)
regulation of smooth muscle cell proliferationCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AHomo sapiens (human)
cAMP-mediated signalingCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AHomo sapiens (human)
response to amphetamineCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
locomotory behaviorCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
visual learningCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
monocyte differentiationCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
cellular response to macrophage colony-stimulating factor stimulusCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
dopamine catabolic processCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
serotonin metabolic processCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
cellular response to granulocyte macrophage colony-stimulating factor stimulusCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
cAMP-mediated signalingCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
cAMP-mediated signalingCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CHomo sapiens (human)
cytoskeleton organizationG-protein coupled receptor 35Homo sapiens (human)
G protein-coupled receptor signaling pathwayG-protein coupled receptor 35Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationG-protein coupled receptor 35Homo sapiens (human)
chemokine-mediated signaling pathwayG-protein coupled receptor 35Homo sapiens (human)
negative regulation of voltage-gated calcium channel activityG-protein coupled receptor 35Homo sapiens (human)
negative regulation of neuronal action potentialG-protein coupled receptor 35Homo sapiens (human)
positive regulation of Rho protein signal transductionG-protein coupled receptor 35Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayG-protein coupled receptor 35Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (18)

Processvia Protein(s)Taxonomy
magnesium ion bindingcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activitycGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cGMP-stimulated cyclic-nucleotide phosphodiesterase activitycGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
protein bindingcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
zinc ion bindingcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cAMP bindingcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cGMP bindingcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
TPR domain bindingcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
phosphate ion bindingcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
protein homodimerization activitycGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activitycGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
alkaline phosphatase activityAlkaline phosphatase, germ cell typeHomo sapiens (human)
metal ion bindingAlkaline phosphatase, germ cell typeHomo sapiens (human)
calmodulin-activated dual specificity 3',5'-cyclic-GMP, 3',5'-cyclic-AMP phosphodiesterase activityCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AHomo sapiens (human)
calmodulin bindingCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AHomo sapiens (human)
metal ion bindingCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AHomo sapiens (human)
calmodulin-activated 3',5'-cyclic-GMP phosphodiesterase activityCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AHomo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activityCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
calmodulin-activated dual specificity 3',5'-cyclic-GMP, 3',5'-cyclic-AMP phosphodiesterase activityCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
protein bindingCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
calmodulin bindingCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
metal ion bindingCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activityCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
calmodulin-activated 3',5'-cyclic-GMP phosphodiesterase activityCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activityCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CHomo sapiens (human)
calmodulin-activated dual specificity 3',5'-cyclic-GMP, 3',5'-cyclic-AMP phosphodiesterase activityCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CHomo sapiens (human)
calmodulin bindingCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CHomo sapiens (human)
metal ion bindingCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activityCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CHomo sapiens (human)
calmodulin-activated 3',5'-cyclic-GMP phosphodiesterase activityCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CHomo sapiens (human)
C-X-C chemokine receptor activityG-protein coupled receptor 35Homo sapiens (human)
G protein-coupled receptor activityG-protein coupled receptor 35Homo sapiens (human)
C-X-C chemokine receptor activityG-protein coupled receptor 35Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
plasma membranecGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
nucleuscGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cytoplasmcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
mitochondrial outer membranecGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
mitochondrial inner membranecGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
endoplasmic reticulumcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
Golgi apparatuscGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cytosolcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
plasma membranecGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
presynaptic membranecGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
perinuclear region of cytoplasmcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
nucleuscGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
mitochondrial inner membranecGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
perinuclear region of cytoplasmcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
mitochondrial outer membranecGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
synaptic membranecGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
cytosolcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
mitochondrial matrixcGMP-dependent 3',5'-cyclic phosphodiesteraseHomo sapiens (human)
extracellular regionAlkaline phosphatase, germ cell typeHomo sapiens (human)
plasma membraneAlkaline phosphatase, germ cell typeHomo sapiens (human)
side of membraneAlkaline phosphatase, germ cell typeHomo sapiens (human)
plasma membraneAlkaline phosphatase, germ cell typeHomo sapiens (human)
cytosolCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AHomo sapiens (human)
neuronal cell bodyCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AHomo sapiens (human)
cytosolCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
neuronal cell bodyCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BHomo sapiens (human)
lysosomeCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CHomo sapiens (human)
cytosolCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CHomo sapiens (human)
neuronal cell bodyCalcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1CHomo sapiens (human)
plasma membraneG-protein coupled receptor 35Homo sapiens (human)
plasma membraneG-protein coupled receptor 35Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID1775491Agonist activity at human GPR35 receptor expressed in HEK293T cells co-expressing beta-arrestin2 assessed as induction of beta-arrestin2 recruitment by BRET assay2021Journal of medicinal chemistry, 03-11, Volume: 64, Issue:5
Structure-Activity Relationship Studies of Coumarin-like Diacid Derivatives as Human G Protein-Coupled Receptor-35 (hGPR35) Agonists and a Consequent New Design Principle.
AID158293Inhibition of cyclic GMP sensitive phosphodiesterase PDE 2 of human lung1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
A new generation of phosphodiesterase inhibitors: multiple molecular forms of phosphodiesterase and the potential for drug selectivity.
AID3283550% inhibition of human placental alkaline phosphatase in the presence of 10 mM p-nitrophenyl phosphate as substrate1982Journal of medicinal chemistry, Jun, Volume: 25, Issue:6
Alkaline phosphatase inhibition by a series of pyrido[2,1-b]quinazolines: A possible relationship with cromolyn-like antiallergy activity.
AID1149801Ratio of cromolyn sodium ID50 to compound ID50 for inhibition of passive cutaneous anaphylaxis reaction in Sprague-Dawley rat1977Journal of medicinal chemistry, Oct, Volume: 20, Issue:10
Quinoline derivatives as antiallergy agents. 2. Fused-ring quinaldic acids.
AID1149800Antiallergic activity against anti-egg albumin homocytotropic antibody injected Sprague-Dawley rat assessed as inhibition of passive cutaneous anaphylaxis reaction administered iv at the time of egg albumin antigen challenge or ip 30 mins prior to egg alb1977Journal of medicinal chemistry, Oct, Volume: 20, Issue:10
Quinoline derivatives as antiallergy agents. 2. Fused-ring quinaldic acids.
AID32834Concentration required for 50% inhibition of human leukocyte alkaline phosphatase in the presence of 10 mM p-nitrophenyl phosphate as substrate1982Journal of medicinal chemistry, Jun, Volume: 25, Issue:6
Alkaline phosphatase inhibition by a series of pyrido[2,1-b]quinazolines: A possible relationship with cromolyn-like antiallergy activity.
AID158892Inhibition of [Ca(2+)]/calmodulin dependent phosphodiesterase PDE 1 of human lung1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
A new generation of phosphodiesterase inhibitors: multiple molecular forms of phosphodiesterase and the potential for drug selectivity.
AID158305Inhibition of low Km cAMP phosphodiesterase PDE III of human lung1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
A new generation of phosphodiesterase inhibitors: multiple molecular forms of phosphodiesterase and the potential for drug selectivity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (77.78)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's1 (11.11)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (18.18%)5.53%
Reviews1 (9.09%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (72.73%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]