An active metabolite of benzbromarone
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Parent Compound(s)
19768Benzbromarone
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Benzarone

Item No. 34903

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2-ethyl-3-benzofuranyl)(4-hydroxyphenyl)-methanone
CAS Number
1477-19-6
Synonyms
  • L 2197
  • NSC 82134
Molecular Formula
C17H14O3
Formula Weight
266.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/ml
λmax
231, 284 nm
SMILES
O=C(C1=C(CC)OC2=CC=CC=C12)C3=CC=C(C=C3)O
InChi Code
InChI=1S/C17H14O3/c1-2-14-16(13-5-3-4-6-15(13)20-14)17(19)11-7-9-12(18)10-8-11/h3-10,18H,2H2,1H3
InChi Key
RFRXIWQYSOIBDI-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 g

    $49

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    5 g

    $223

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    10 g

    $423

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    Cayman Chemical
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    Product Description

    Benzarone is an active metabolite of the urate anion transporter 1 (URAT1) inhibitor benzbromarone (Item No. 19768).1,2 It inhibits URAT1 in Xenopus oocytes expressing the human enzyme (IC50 = 2.8 µM).2 Benzarone also inhibits the tyrosine phosphatase activity of eyes absent homolog 3 (EYA3; IC50 = 17.5 µM), as well as reduces the proliferation and migration of human umbilical vein endothelial cells (HUVECs) when used at a concentration of 7.5 µM.3 It uncouples oxidative phosphorylation in isolated rat liver mitochondria and induces apoptosis and necrosis in isolated rat hepatocytes.4 Benzarone (25 µg/g) reduces tumor growth in an A-673 Ewing sarcoma mouse xenograft model.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Stüber, W., and Möller, H. Determination of benzbromarone, bromobenzarone and benzarone in plasma by gas chromatography—mass spectrometry. J. Chromatogr. B Biomed. Sci. Appl. 224(2), 327-331 (1981).

    2. Wempe, M.F., Jutabha, P., Quade, B., et al. Developing potent human uric acid transporter 1 (hURAT1) inhibitors. J. Med. Chem. 54(8), 2701-2713 (2011).

    3. Pandey, R.N., Wang, T.S., Tadjuidje, E., et al. Structure-activity relationships of benzbromarone metabolites and derivatives as EYA inhibitory anti-angiogenic agents. PLoS One 8(12), e84582 (2013).

    4. Kaufmann, P., Török, M., Hänni, A., et al. Mechanisms of benzarone and benzbromarone-induced hepatic toxicity. Hepatology 41(4), 925-935 (2005).

    5. Wang, Y., Pandey, R.N., Roychoudhury, K., et al. Targeting EYA3 in ewing sarcoma retards tumor growth and angiogenesis. Mol. Cancer Ther. 20(5), 803-815 (2021).