Bipenquinate Chemical Properties

Melting point:

>360°

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)

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

Safety Information

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

Bipenquinate Usage And Synthesis

Description

Brequinar sodium (96201-88-6) is an inhibitor of dihydroorotate dehydrogenase (DHODH)1,2with IC50’s between 0.2 and 5.8 μM in various cell lines3and 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.4Brequinar 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] S F CHEN  D L D  R L Ruben. Mechanism of action of the novel anticancer agent 6-fluoro-2-(2’-fluoro-1,1’-biphenyl-4-yl)-3-methyl-4-quinolinecarbo xylic acid sodium salt (NSC 368390): inhibition of de novo pyrimidine nucleotide biosynthesis.[J]. Cancer research, 1986, 46 10: 5014-5019.
[2] G J PETERS. In vivo inhibition of the pyrimidine de novo enzyme dihydroorotic acid dehydrogenase by brequinar sodium (DUP-785; NSC 368390) in mice and patients.[J]. Cancer research, 1990, 50 15: 4644-4649.
[3] E. DE KANT. The relation between inhibition of cell growth and of dihydroorotic acid dehydrogenase by Brequinar Sodium[J]. Cancer letters, 1989, 46 2: Pages 123-127. DOI:10.1016/0304-3835(89)90019-0
[4] D. SYKES. Inhibition of Dihydroorotate Dehydrogenase Overcomes Differentiation Blockade in Acute Myeloid Leukemia[J]. Cell, 2016, 167 1: 171-186.e15. DOI:10.1016/j.cell.2016.08.057
[5] MIN QING. Characterization of dengue virus resistance to brequinar in cell culture.[J]. Antimicrobial Agents and Chemotherapy, 2010: 3686-3695. DOI:10.1128/aac.00561-10
[6] PETTER I. ANDERSEN. Novel Antiviral Activities of Obatoclax, Emetine, Niclosamide, Brequinar, and Homoharringtonine[J]. Viruses-Basel, 2019. DOI:10.3390/v11100964
[7] JUN-GYU PARK. Identification and Characterization of Novel Compounds with Broad-Spectrum Antiviral Activity against Influenza A and B Viruses.[J]. Journal of Virology, 2020. DOI:10.1128/jvi.02149-19

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