| Identification | Back Directory | [Name]
Bipenquinate | [CAS]
96201-88-6 | [Synonyms]
CS-340
Dup-785
NSC-368390
Bipenquinate
Brequinar sodium
Brequinar sodium
(DuP-785
6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methylquinoline-4-carboxylate
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
2-(2'-Fluoro-1,1'-biphenyl-4-yl)-3-methyl-6-fluoroquinoline-4-carboxylic acid sodium salt | [EINECS(EC#)]
604-604-1 | [Molecular Formula]
C23H14F2NNaO2 | [MOL File]
96201-88-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
>360° | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Soluble in DMSO (up to at least 25 mg/ml) or in Water (up to 15 mg/ml with warming) | [form ]
solid | [color ]
Off-white or white | [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. | [InChI]
1S/C23H15F2NO2.Na/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);/q;+1/p-1 | [InChIKey]
PZOHOALJQOFNTB-UHFFFAOYSA-M | [SMILES]
[Na+].Fc1c(cccc1)c2ccc(cc2)c3nc4c(c(c3C)C(=O)[O-])cc(cc4)F |
| Hazard Information | Back Directory | [Description]
Brequinar sodium (96201-88-6) is an inhibitor of dihydroorotate dehydrogenase (DHODH)1,2?with IC50’s between 0.2 and 5.8 μM in various cell lines3?and 20 nM in isolated enzyme4. It reduced leukemic cell burden, decreased levels of leukemia-initiating cells, and improved survival in human and mouse models of acute myeloid leukemia.4?Brequinar displayed broad antiviral activity against flaviviruses, positive-strand RNA alphaviruses, negative-strand RNA rhabdoviruses, Influenza A and B viruses, and HIV.5-7 | [Uses]
Antineoplastic. | [Definition]
ChEBI: Brequinar sodium is an organic sodium salt of brequinar. It has a role as an anticoronaviral agent, an antineoplastic agent, an antiviral agent, an EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor, an immunosuppressive agent, a pyrimidine synthesis inhibitor and an antimetabolite. It contains a brequinar(1-). | [storage]
Store at +4°C | [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 |
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