96201-88-6

Basic information

• Product Name: Bipenquinate
• Synonyms: Bipenquinate;Brequinar sodium;2-(2'-Fluoro-1,1'-biphenyl-4-yl)-3-methyl-6-fluoroquinoline-4-carboxylic acid sodium salt;Dup-785;NSC-368390;SODIUM 6-FLUORO-2-(2-FLUORO-[1,1-BIPHENYL]-4-YL)-3-METHYLQUINOLINE-4-CARBOXYLATE
• CAS NO: 96201-88-6
• Molecular Formula: C23H15 F2 N O2 . Na
• Molecular Weight: 0
• EINECS: 604-604-1
• Mol File: 96201-88-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: >360°
• Boiling Point: 550.9°Cat760mmHg
• Flash Point: 287°C
• Appearance: /
• Density: g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Soluble in DMSO (up to at least 25 mg/ml) or in Water (up to 15 mg/ml with warming)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month.
• CAS DataBase Reference: Bipenquinate(CAS DataBase Reference)
• NIST Chemistry Reference: Bipenquinate(96201-88-6)
• EPA Substance Registry System: Bipenquinate(96201-88-6)

Safety Data

• Hazardous Substances Data: 96201-88-6(Hazardous Substances Data)

Usage

Description

Brequinar sodium is an inhibitor of dihydroorotate dehydrogenase (DHODH) with IC50 values ranging from 0.2 to 5.8 μM in various cell lines and 20 nM in isolated enzyme. It has demonstrated efficacy in reducing leukemic cell burden, decreasing levels of leukemia-initiating cells, and improving survival in human and mouse models of acute myeloid leukemia. Additionally, Brequinar has shown broad antiviral activity against various types of viruses, including flaviviruses, positive-strand RNA alphaviruses, negative-strand RNA rhabdoviruses, Influenza A and B viruses, and HIV.

Uses

Used in Antineoplastic Applications:
Brequinar sodium is used as an antineoplastic agent for its ability to inhibit the activity of dihydroorotate dehydrogenase (DHODH), a key enzyme involved in the de novo pyrimidine biosynthesis pathway. This inhibition leads to the suppression of DNA synthesis and cell proliferation, making it a potential therapeutic agent for the treatment of various types of cancer.
Used in Antiviral Applications:
Brequinar sodium is used as an antiviral agent due to its broad-spectrum activity against various types of viruses, including flaviviruses, positive-strand RNA alphaviruses, negative-strand RNA rhabdoviruses, Influenza A and B viruses, and HIV. Its antiviral properties make it a promising candidate for the development of treatments for viral infections.

References

1) Chen?et al.?(1986)?Mechanism of action of the novel anticancer agent 6-fluoro-2-(2’-fluoro-1,1’-biohenyl-4-yl)-3-methyl-4-quinolinecarboxylic acid sodium salt (NSC 368390): inhibition of de novo pyrimidine nucleotide biosynthesis;?Cancer Res.,?46?5014 2) Peters?et al.?(1990)?In vivo inhibition of the pyrimidine de novo enzyme dihydroorotic aicd dehydrogenase by brequinar sodium (DUP-785; NSC 368390) in mice and patients;?Cancer Res.,?50?4644 3) De Kant?et al.?(1989) The relation between inhibition of cell growth and of dihydroorotic acid dehydrogenase by brequinar sodium; Cancer Lett.,?46?123 4) Sykes?et al.?(2016)?Inhibition of Dihydroorotate Overcomes Differentiation Blockade in Acute Myeloid Leukemia;?Cell,?167?171 5) Qing?et al. (2010)?Characterization of Dengue Virus Resistance to Brequinar in Cell Culture;?Antimicrob. Agents Chemother.,?54?3686 6) Andersen?et al.?(2019)?Novel Antiviral Activities of Obatoclax, Emetine, Niclosamide, Brequinar, and Homoharringtonine;?Viruses,?11?E964 7) Park?et al.?(2020)?Identification and Characterization of Novel Compounds with Broad-Spectrum Antiviral Activity against Influenza A and B Viruses;?J. Virol.,?94?e02149