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Brequinar

CAT: 0013-GTR19158822-09Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19158822-09Size:100 mg
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Description
Brequinar is a potent inhibitor of dihydroorotate dehydrogenase with potent activities against a broad spectrum of viruses. (In Vitro) :Brequinar reduces virus progeny production by >90%, with EC50 of 17 nM. Brequinar (5 μM) also inhibits other orthopoxviruses, and blocks virus DNA replication. Brequinar does not affect virus early gene expression, but has a severe effect on the late stage of the virus cycle. Brequinar reduces the level of envelope protein production and the viral titer in a dose-dependent manner, with EC50 of 78 nM in the CFI assay. Brequinar (5 μM) inhibits viral RNA synthesis. Brequinar has antiviral effect, but the effect is reversed by pyrimidine. Brequinar-resistant viruses can be selected in cell culture. Brequinar (5 μM) suppresses the luciferase activities from both the WT and NS5 mutant replicons. Brequinar sodium effectively prevents the increase in PyNTP levels with an IC50 of 0.26 μM. Brequinar sodium effectively inhibits cell proliferation with an IC50 of 0.26 μM. Brequinar sodium inhibits autophosphorylation of p56lck with IC50 of 70 μM; inhibition is 39, 41, and 60% for 25, 50, and 100 μM Brequinar sodium, respectively. Brequinar sodium also inhibits the phosphorylation by p56lck of the exogenous substrate, histone 2B, with an IC50 of 70 μM; inhibition is 10, 43, 59, and 86% for 25, 50, 100, and 200 μM Brequinar sodium, respectively. Brequinar sodium inhibits autophosphorylation of p59fyn with an IC50 of 105 μM; inhibition is 0, 17, 48, and 65% for 25, 50, 100, and 200 μM Brequinar sodium, respectively. Brequinar sodium also inhibits the phosphorylation by p59fyn of histone 2B with an IC50 of 20 μM; inhibition is 26, 54, 79, 83, and 84% for 10, 25, 50, 100, and 200 μM Brequinar sodium, respectively. (In Vivo) :Brequinar sodium-treated (10-20 mg/kg/day) mice has a 31% reduction in percentage of packed cell volume compared with untreated BALB/c mice. Brequinar sodium reduces UTP and CTP levels in bone marrow cells by 30 and 25%, respectively. Brequinar sodium (10-20 mg/kg/day) in combination with uridine (1000-2000 mg/kg/day) prevents anemia, and the hematocrits remain at levels (61-63%) comparable with those of untreated controls.
CAS Number
96187-53-0
Product Name Alternative
NSC 368390 | DUP785 | Bipenquinate
Purity
>98% (HPLC)
Solubility
DMSO:≥ 62.5 mg/mL (166.50 mM)
Smiles
Cc1c (nc2ccc (F) cc2c1C (O) =O) -c1ccc (cc1) -c1ccccc1F
Molecular Formula
C22H13F2NO2
Molecular Weight
375.37
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.

Chemical Information

Brequinar

Brequinar is a quinolinemonocarboxylic acid that is quinoline substituted by 2'-fluoro[1,1'-biphenyl]-4-yl, methyl, carboxy and fluoro groups at positions 2, 3, 4, and 6, respectively. It is an inhibitor of dihydroorotate dehydrogenase, an enzyme that is required for de novo pyrimidine biosynthesis. The compound exhibits antineoplastic and antiviral properties. It has a role as an anticoronaviral agent, an antiviral agent, an antimetabolite, an antineoplastic agent, an immunosuppressive agent, a pyrimidine synthesis inhibitor and an EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor. It is a member of biphenyls, a monocarboxylic acid, a quinolinemonocarboxylic acid and a member of monofluorobenzenes. It is a conjugate acid of a brequinar(1-).

CAS Number96187-53-0
PubChem CID57030
IUPAC Name6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methylquinoline-4-carboxylic acid
Molecular FormulaC23H15F2NO2
Molecular Weight375.4
XLogP5.6
Topological Polar Surface Area50.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Heavy Atom Count28
Formal Charge0
Complexity551
SMILES
CC1=C(C2=C(C=CC(=C2)F)N=C1C3=CC=C(C=C3)C4=CC=CC=C4F)C(=O)O
InChI
InChI=1S/C23H15F2NO2/c1-13-21(23(27)28)18-12-16(24)10-11-20(18)26-22(13)15-8-6-14(7-9-15)17-4-2-3-5-19(17)25/h2-12H,1H3,(H,27,28)
InChIKey
PHEZJEYUWHETKO-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Brequinar
CAS: 96187-53-0
CID: 57030
Formula: C23H15F2NO2
MW: 375.4
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight375.4
XLogP35.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass375.10708505
Monoisotopic Mass375.10708505
Topological Polar Surface Area50.2 Ų
Heavy Atom Count28
Formal Charge0
Complexity551
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes