Compounds > brequinar sodium
Page last updated: 2024-11-13

brequinar sodium

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Description

brequinar sodium : An organic sodium salt of brequinar. [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]

Cross-References

ID SourceID
PubMed CID23663964
CHEMBL ID300058
CHEBI ID177871
SCHEMBL ID4265
MeSH IDM0322526

Synonyms (55)

Synonym
bipenquinate
6-fluoro-2-(2'-fluoro-1,1'-biphenyl-4-yl)-3-methyl-4-quinoline-carboxylic acid sodium salt
sodium 6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-methylquinoline-4-carboxylate
CHEBI:177871
sodium 6-fluoro-2-(2'-fluoro[biphenyl]-4-yl)-3-methylquinoline-4-carboxylate
dup-785
brequinar sodium (usan)
D03154
dup 785
nsc-368390
96201-88-6
brequinar sodium
nsc 368390
CHEMBL300058 ,
brequinar sodium salt
6-fluoro-2-(2'-fluoro-1,1'-biphenyl-4-yl)-3-methyl-4-quinolinecarboxylic acid sodium
4-quinolinecarboxylic acid, 6-fluoro-2-(2'-fluoro(1,1'-biphenyl)-4-yl)-3-methyl-, sodium salt
unii-49eef6hrus
49eef6hrus ,
brequinar sodium [usan]
sodium 6-fluoro-2-(2'-fluoro-4-biphenylyl)-3-methyl-4-quinolinecarboxylate
S3565
brequinar sodium [who-dd]
brequinar sodium salt [mi]
brequinar sodium [mart.]
2-(2'-fluoro-1,1'-biphenyl-4-yl)-6-fluoro-3-methylquinoline-4-carboxylic acid sodium salt
CCG-221414
SCHEMBL4265
PZOHOALJQOFNTB-UHFFFAOYSA-M
sodium 2-(2'-fluoro-1,1'-biphenyl-4-yl)-6-fluoro-3-methylquinoline-4-carboxylate
AC-35373
sodium 6-fluoro-2-(2'-fluoro-[1,1'-biphenyl]-4-yl)-3-methylquinoline-4-carboxylate
6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-methyl-4-quinolinecarboxylic acid sodium
DTXSID30242173
AKOS027326512
sodium 6-fluoro-2-{2'-fluoro-[1,1'-biphenyl]-4-yl}-3-methylquinoline-4-carboxylate
AS-74463
c23h14f2nnao2
J-505616
FT-0731026
AKOS032962879
mfcd22648381
dup785 (sodium); nsc 368390 (sodium)
brequinar (sodium)
4-quinolinecarboxylic acid,6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-methyl-, sodium salt
F52273
Q27259277
2-(2'-fluoro-1,1'-biphenyl-4-yl)-3-methyl-6-fluoroquinoline-4-carboxylic acid sodium salt;brequinar sodium
A847267
sodium;6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methylquinoline-4-carboxylate
dihydroorotate dehydrogenase inhibitor, brequinar
WDA20188
bipenquinate, brq, dup-785, nsc 368390
HY-108325A
CS-0033939
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (7)

RoleDescription
anticoronaviral agentAny antiviral agent which inhibits the activity of coronaviruses.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
antiviral agentA substance that destroys or inhibits replication of viruses.
EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitorAn EC 1.3.5.* (oxidoreductase acting on CH-CH of donor with a quinone or related compound as acceptor) inhibitor that interferes with the action of dihydroorotate dehydrogenase (quinone), EC 1.3.5.2.
immunosuppressive agentAn agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
pyrimidine synthesis inhibitorA pathway inhibitor that inhibits the synthesis of pyrimidine.
antimetaboliteA substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
[role 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]

Drug Classes (1)

ClassDescription
organic sodium salt
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)IC50 (µMol)0.01550.00050.742710.0000AID1155723; AID1624954
Dihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)Ki0.01200.01200.50372.7000AID55742; AID55743
[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)
Dihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)EC50 (µMol)0.05490.05494.68438.9125AID1687332
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
UDP biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
'de novo' UMP biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
pyrimidine ribonucleotide biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
'de novo' pyrimidine nucleobase biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
dihydroorotase activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
protein bindingDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
dihydroorotate dehydrogenase (quinone) activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
dihydroorotate dehydrogenase activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleoplasmDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrionDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrial inner membraneDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
cytosolDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrial inner membraneDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID1687332Inhibition of DHODH in human HEK-293 cells transfected with ISRE-luciferase reporter gene assessed as increase in IFN-alpha mediated cellular response upto 72 hrs by luciferase reporter gene assay2020European journal of medicinal chemistry, Jan-15, Volume: 186Cerpegin-derived furo[3,4-c]pyridine-3,4(1H,5H)-diones enhance cellular response to interferons by de novo pyrimidine biosynthesis inhibition.
AID1155724Antiproliferative activity against human A375 cells at 0.01 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155729Antiproliferative activity against human A375 cells at 1.23 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155734Antiproliferative activity against human Hep3B cells at 0.01 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155740Antiproliferative activity against human Hep3B cells at 3.7 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID55742Inhibition of human recombinant dihydroorotate dehydrogenase (DHODase)1998Bioorganic & medicinal chemistry letters, Feb-03, Volume: 8, Issue:3
Structure-activity relationships (SAR) of some tetracyclic heterocycles related to the immunosuppressive agent Brequinar Sodium.
AID1155741Antiproliferative activity against human Hep3B cells at 11.11 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155736Antiproliferative activity against human Hep3B cells at 0.05 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155725Antiproliferative activity against human A375 cells at 0.02 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155739Antiproliferative activity against human Hep3B cells at 1.23 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155737Antiproliferative activity against human Hep3B cells at 0.14 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155723Inhibition of recombinant human DHODH activity after 20 mins by DCIP dye based colorimetric analysis in presence of 1 mM L-dihydroorotate and 1 mM CqD2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID90465Ability to inhibit proliferation in a mixture of human lymphocytes from two unrelated donors in MLR (human mixed lymphocyte reaction)1998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Heteroatom- and carbon-linked biphenyl analogs of Brequinar as immunosuppressive agents.
AID1155732Antiproliferative activity against human A375 cells at 33.33 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1624956Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by MTT assay2019Bioorganic & medicinal chemistry letters, 04-01, Volume: 29, Issue:7
Synthesis of 2-,4,-6-, and/or 7-substituted quinoline derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents: 3D QSAR-assisted design.
AID1155731Antiproliferative activity against human A375 cells at 11.11 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID55743Immunosuppressive effect in an isolated enzyme assay using partially purified Dihydroorotate dehydrogenase from human liver for inhibition of the formation of orotate from radiolabeled dihydroorotate1998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Heteroatom- and carbon-linked biphenyl analogs of Brequinar as immunosuppressive agents.
AID1155727Antiproliferative activity against human A375 cells at 0.14 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1624954Inhibition of human recombinant N-terminal His-tagged DHODH (31 to 395 residues) expressed in Escherichia coli using DHO as substrate measured after 20 mins by DCPI dye-based assay2019Bioorganic & medicinal chemistry letters, 04-01, Volume: 29, Issue:7
Synthesis of 2-,4,-6-, and/or 7-substituted quinoline derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents: 3D QSAR-assisted design.
AID1155743Antiproliferative activity against human Hep3B cells at 100 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155735Antiproliferative activity against human Hep3B cells at 0.02 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID90468Concentration required to inhibit proliferation in a mixture of human lymphocytes using mixed lymphocyte reaction test1998Bioorganic & medicinal chemistry letters, Feb-03, Volume: 8, Issue:3
Structure-activity relationships (SAR) of some tetracyclic heterocycles related to the immunosuppressive agent Brequinar Sodium.
AID1155722Inhibition of recombinant human DHODH activity at 10 uM after 20 mins by DCIP dye based colorimetric analysis in presence of 1 mM L-dihydroorotate and 1 mM CqD2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155728Antiproliferative activity against human A375 cells at 0.41 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155730Antiproliferative activity against human A375 cells at 3.7 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155744Antiproliferative activity against human Hep3B cells for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155745Antiproliferative activity against human A375 cells for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155726Antiproliferative activity against human A375 cells at 0.05 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155742Antiproliferative activity against human Hep3B cells at 33.33 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155738Antiproliferative activity against human Hep3B cells at 0.41 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1155733Antiproliferative activity against human A375 cells at 100 ug/ml for 24 hrs by MTT assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design, synthesis and pharmacological evaluation of novel substituted quinoline-2-carboxamide derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents.
AID1624955Antiproliferative activity against human HT-29 cells after 48 hrs by MTT assay2019Bioorganic & medicinal chemistry letters, 04-01, Volume: 29, Issue:7
Synthesis of 2-,4,-6-, and/or 7-substituted quinoline derivatives as human dihydroorotate dehydrogenase (hDHODH) inhibitors and anticancer agents: 3D QSAR-assisted design.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (28.57)18.2507
2000's0 (0.00)29.6817
2010's3 (42.86)24.3611
2020's2 (28.57)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.87

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 Index19.87 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.87)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		2.2110taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
vidofludimus
vidofludimus: a dihydroorotate dehydrogenase inhibitor; structure in first source		2.2510
teriflunomide
[no description available]		2.2510(trifluoromethyl)benzenes;
aromatic amide;
enamide;
enol;
nitrile;
secondary carboxamide		drug metabolite;
EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor;
hepatotoxic agent;
non-steroidal anti-inflammatory drug;
tyrosine kinase inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Plasmodium falciparum Malaria
[description not available]		02.110
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		02.110