An internal standard for the quantification of ethacrynic acid
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Unlabeled Version(s)
19536Ethacrynic Acid
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Ethacrynic Acid-d5

Item No. 28537

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(2,3-dichloro-4-(2-methylenebutanoyl-3,3,4,4,4-d5)phenoxy)acetic acid
CAS Number
1330052-59-9
Molecular Formula
C13H7Cl2D5O4
Formula Weight
308.2
Purity
≥99% deuterated forms (d1-d5)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly solubleMethanol: slightly soluble
SMILES
O=C(C(C([2H])([2H])C([2H])([2H])[2H])=C)C1=C(Cl)C(Cl)=C(OCC(O)=O)C=C1
InChi Code
InChI=1S/C13H12Cl2O4/c1-3-7(2)13(18)8-4-5-9(12(15)11(8)14)19-6-10(16)17/h4-5H,2-3,6H2,1H3,(H,16,17)/i1D3,3D2
InChi Key
AVOLMBLBETYQHX-WNWXXORZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    2 mg

    $502

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    Product Description

    Ethacrynic acid-d5 is intended for use as an internal standard for the quantification of ethacrynic acid (Item No. 19536) by GC- or LC-MS. Ethacrynic acid is a loop diuretic with anticancer activity.1,2,3 It inhibits the Na-K-2Cl (NKCC) cotransporter in duck erythrocytes (IC50 = 0.18 mM) and ATP-dependent chloride uptake in rat renal plasma membrane vesicles when used at a concentration of 0.3 mM.1,4 Ethacrynic acid also inhibits glutathione S-transferase P1-1 (GSTP1-1) and GSTA3-3 (IC50s = 4.9 and ~0.4 μM, respectively), and inhibits Wnt/β-catenin signaling in a cell-based reporter assay.2,5 It is cytotoxic to primary chronic lymphocytic leukemia cells (IC50 = 8.56 μM), as well as MCF-7, MDA-MB-231, and 4T1 cancer cells (IC50s = 45.53, 39.64, and 25.23 μM, respectively).2,3 Ethacrynic acid (250 μg per day) increases tumor growth reduction induced by the EGFR family inhibitors afatinib (Item Nos. 11492 | 21567 ) or neratinib (Item No. 18404) in a 4T1 murine breast cancer model.3 Formulations containing ethacrynic acid have been used in the treatment of edema.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Palfrey, H.C., and Leung, S. Inhibition of Na-K-2Cl cotransport and bumetanide binding by ethacrynic acid, its analogues, and adducts. Am. J. Physiol. 264(5 Pt 1), C1270-C1277 (1993).

    2. Lu, D., Liu, J.X., Endo, T., et al. Ethacrynic acid exhibits selective toxicity to chronic lymphocytic leukemia cells by inhibition of the Wnt/beta-catenin pathway. PLoS One 4(12), e8294 (2009).

    3. Liu, B., Huang, X., Hu, Y., et al. Ethacrynic acid improves the antitumor effects of irreversible epidermal growth factor receptor tyrosine kinase inhibitors in breast cancer. Oncotarget 7(36), 58038-58050 (2016).

    4. Kunugi, Y., Hiraoka, Y., Hashimoto, Y., et al. Ethacrynic acid-sensitive and ATP-dependent Cl- transport in the rat kidney. Jpn. J. Pharmacol. 57(2), 167-174 (1991).

    5. Musdal, Y., Hegazy, U.M., Aksoy, Y., et al. FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. Chem. Biol. Interact. 205(1), 53-62 (2013).