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SML0113

Sigma-Aldrich

Brequinar sodium salt hydrate

≥97% (HPLC)

Synonym(e):

6-Fluoro-2-(2′-fluoro[1,1′-biphenyl]-4-yl)-3-methyl-4-quinolinecarboxylic acid sodium hydrate, Biphenquinate sodium hydrate, DuP 785 hydrate, NSC 368390 hydrate

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About This Item

Empirische Formel (Hill-System):
C23H14F2NO2·Na · xH2O
CAS-Nummer:
96187-53-0
Molekulargewicht:
397.35 (anhydrous basis)
MDL-Nummer:
MFCD21363375
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329825165
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥97% (HPLC)

Form

powder

Farbe

off-white to brown

Löslichkeit

DMSO: ≥5 mg/mL

Lagertemp.

2-8°C

SMILES String

O.[Na+].Cc1c(nc2ccc(F)cc2c1C([O-])=O)-c3ccc(cc3)-c4ccccc4F

InChI

1S/C23H15F2NO2.Na.H2O/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);;1H2/q;+1;/p-1

InChIKey

IZXTTXFXRQGHKO-UHFFFAOYSA-M

Anwendung

Brequinar sodium salt hydrate has been used as a dihydroorotate dehydrogenase (DHODH) inhibitor:
  • in drug response assays
  • to induce depletion of cellular pyrimidine pools
  • in cell proliferation assays

Brequinar sodium salt hydrate may be used in cell signaling studies.

Biochem./physiol. Wirkung

Brequinar exhibits anti-neoplastic activity against refractory solid tumors in human and mouse models. Continuous treatment is required for depletion of pyrimidine pools in the cancer cells and tumor inhibition.
Brequinar inhibits dihydroorotate dehydrogenase (DHODH), the fourth enzyme in the de novo pyrimidine biosynthesis pathway, preventing the synthesis of DNA and RNA. Brequinar has recently been found to have antiviral activity against a broad spectrum of viruses including flaviviruses (dengue virus, West Nile virus, yellow fever virus, and Powassan virus) and also a plus-strand RNA alphavirus (Western equine encephalitis virus) and a negative-strand RNA rhabdovirus (vesicular stomatitis virus).

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Identification of new activators of mitochondrial fusion reveals a link between mitochondrial morphology and pyrimidine metabolism
Miret-Casals L, et al.
Cell Chemical Biology, 25(3), 268-278 (2018)
PTEN regulates glutamine flux to pyrimidine synthesis and sensitivity to dihydroorotate dehydrogenase inhibition
Mathur D, et al.
Cancer Discovery, 7(4), 380-390 (2017)
Oncogenic KRAS supports pancreatic cancer through regulation of nucleotide synthesis
Santana-Codina N, et al.
Nature Communications, 9(1), 4945-4945 (2018)
C L Arteaga et al.
Cancer research, 49(16), 4648-4653 (1989-08-15)
Brequinar sodium is a 4-quinolinecarboxylic acid analogue that inhibits dihydroorotate dehydrogenase and subsequent de novo pyrimidine biosynthesis. It has shown dose-dependent antineoplastic activity against several mouse and human tumor models. This trial evaluated Brequinar given as a single daily i.v.
Thale Kristin Olsen et al.
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Despite intensive therapy, children with high-risk neuroblastoma are at risk of treatment failure. We applied a multiomic system approach to evaluate metabolic vulnerabilities in human neuroblastoma. We combined metabolomics, CRISPR screening, and transcriptomic data across more than 700 solid tumor
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