| Identification | Back Directory | [Name]
Brequinar | [CAS]
96187-53-0 | [Synonyms]
BPQ
CS-157
Brequinar
Biphenquinate
Brequinar (DUP785)
BREQUINAR;BIPENQUINATE;DUP 785;NSC 368390.
6-Fluoro-2-(2'-fluoro-[1,1'-biphenyl]-4-yl)
6-fluoro-2-(2'-fluorobiphenyl-4-yl)-3-Methylquinoline-4-carboxyl
6-fluoro-2-(2'-fluorobiphenyl-4-yl)-3-methylquinoline-4-carboxylic acid
6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methylquinoline-4-carboxylic acid
6-Fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-methyl-4-quinolinecarboxylic acid
6-Fluoro-2-(2'-fluoro-[1,1'-biphenyl]-4-yl)-3-methylquinoline-4-carboxylic acid
4-Quinolinecarboxylic acid, 6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-Methyl- | [Molecular Formula]
C22H13F2NO2 | [MDL Number]
MFCD00866437 | [MOL File]
96187-53-0.mol | [Molecular Weight]
375.37 |
| Chemical Properties | Back Directory | [Melting point ]
355-357℃ (N,N-dimethylformamide water ) | [storage temp. ]
2-8°C | [solubility ]
DMSO:25.9(Max Conc. mg/mL);70.0(Max Conc. mM) | [form ]
powder to crystal | [pka]
pKa 4.45(H2O t=RT I=0.10) (Uncertain) | [color ]
White to Light yellow | [CAS DataBase Reference]
96187-53-0 |
| Hazard Information | Back Directory | [Uses]
Antineoplastic. | [Definition]
ChEBI: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 EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor, an immunosuppressive agent, an antineoplastic agent, an antiviral agent, a pyrimidine synthesis inhibitor, an anticoronaviral agent and an antimetabolite. It is a member of biphenyls, a member of monofluorobenzenes, a quinolinemonocarboxylic acid and a monocarboxylic acid. It is a conjugate acid of a brequinar(1-). | [Biological Activity]
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 pathwaypreventing the synthesis of DNA and RNA. Brequinar has recently been found to have antiviral activity against a broad spectrum of viruses including flaviviruses (dengue virusWest Nile virusyellow fever virusand Powassan virus) and also a plus-strand RNA alphavirus (Western equine encephalitis virus) and a negative-strand RNA rhabdovirus (vesicular stomatitis virus). | [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[3]. | [storage]
Store at -20°C |
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