SML0113

Brequinar sodium salt hydrate

Name: Brequinar sodium salt hydrate
Brand: SIGMA

≥97% (HPLC), DHODH inhibitor, powder

Synonym(s):

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

Empirical Formula (Hill Notation):

C₂₃H₁₄F₂NO₂·Na · xH₂O

CAS Number:

96187-53-0

Molecular Weight:

397.35 (anhydrous basis)

UNSPSC Code:

12352200

PubChem Substance ID:

329825165

NACRES:

NA.77

MDL number:

MFCD21363375

Product Name

Brequinar sodium salt hydrate, ≥97% (HPLC)

SMILES string

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

InChI key

IZXTTXFXRQGHKO-UHFFFAOYSA-M

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

assay

≥97% (HPLC)

form

powder

color

off-white to brown

solubility

DMSO: ≥5 mg/mL

storage temp.

2-8°C

Quality Level

100

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

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 Actions

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).

Brequinar sodium salt hydrate is a dihydroorotate dehydrogenase (DHODH) inhibitor; antiviral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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PTEN regulates glutamine flux to pyrimidine synthesis and sensitivity to dihydroorotate dehydrogenase inhibition

Mathur D, et al.

Cancer Discovery, 7(4), 380-390 (2017)

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)

Proof-of-principle studies on a strategy to enhance nucleotide imbalance specifically in cancer cells.

Twana Alkasalias et al.

Cell death discovery, 8(1), 464-464 (2022-11-25)

Highly specific and potent inhibitors of dihydroorotate dehydrogenase (DHODH), an essential enzyme of the de novo pyrimidine ribonucleotide synthesis pathway, are in clinical trials for autoimmune diseases, viral infections and cancer. However, because DHODH inhibitors (DHODHi) are immunosuppressants they may

Phase I clinical and pharmacokinetic trial of Brequinar sodium (DuP 785; NSC 368390).

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.

DHODH is an independent prognostic marker and potent therapeutic target in neuroblastoma.

Thale Kristin Olsen et al.

JCI insight, 7(17) (2022-08-10)

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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