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5.08321

Dihydroorotate Dehydrogenase Inhibitor, Brequinar

Name: Dihydroorotate Dehydrogenase Inhibitor, Brequinar
Brand: MM

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₂₃H₁₄F₂NNaO₂

CAS Number:

96201-88-6

Molecular Weight:

397.35

MDL number:

MFCD22648381

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

Storage condition:

OK to freeze, protect from light

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Properties

assay

≥98% (HPLC)

Quality Level

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

Description

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)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c