5.08321

Dihydroorotate Dehydrogenase Inhibitor, Brequinar

• Synonym(e): Dihydroorotate Dehydrogenase Inhibitor, Brequinar, 6-fluoro-2-(2ʹ-fluoro-1,1ʹ-biphenyl-4-yl)-3-methyl-4-quinoline-carboxylic acid sodium salt, NSC 368390, DuP 785, NSC 368390, DuP 785, 6-fluoro-2-(2ʹ-fluoro-1,1ʹ-biphenyl-4-yl)-3-methyl-4-quinoline-carboxylic acid sodium salt
• Empirische Formel (Hill-System): C₂₃H₁₄F₂NNaO₂
• CAS-Nummer: 96201-88-6
• Molekulargewicht: 397.35
• MDL number: MFCD22648381
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥98% (HPLC)
• Form: solid
• Storage condition: OK to freeze, protect from light

Eigenschaften

• assay: ≥98% (HPLC)
• Quality Segment: 100
• form: solid
• potency: 12 nM IC₅₀
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: off-white
• solubility: DMSO: 50 mg/mL
• storage temp.: 2-8°C
• SMILES string: [Na+].Fc1c(cccc1)c2ccc(cc2)c3nc4c(c(c3C)C(=O)[O-])cc(cc4)F
• 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
• InChI key: PZOHOALJQOFNTB-UHFFFAOYSA-M

Beschreibung

General description

A quinolinecarboxylic acid derivative with immunosuppressive and anti-neoplastic properties. Inhibits pyrimidine synthesis by blocking the activity of mammalian mitochondrial dihydroorotate dehydrogenase (DHODH; IC₅₀ = 12 nM). Does not affect DHODH in non-mammalian species. Also reported to inhibit glycosylation of adhesion molecules. Potentiates the sensitivity of U1690 small cell lung cancer cells to TRAIL-induced apoptosis and synergistically enhances the anti-tumor effects of doxorubicin ( ~100 µM).

Biochem/physiol Actions

Cell permeable: yes

Primary Target
DHODH

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

He, T. et al. 2013. Oncogene32, in press.
Hurt, D.E., et al. 2006. Bioorg. Med. Chem. Lett.16, 1610.
Schnellrath, L. et al. 2011. Int. J. Antimicrob. Agents.38, 435.
Batt, D.G., et al. 1995. Bioorg. Med. Chem. Lett.14, 1549.
Allison, A., et al. 1993. Transplantation Proc.25, 67.
Cramer, D. et al. 1992. Transplantation.53, 303.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable