| Field | Specification |
|---|---|
| Target | |
| Alternative names | Etacrynic acid |
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C13H12Cl2O4 |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Ethacrynic acid, also known as Etacrynic acid, has anti-inflammatory and anticancer activity and is an orally active diuretic. It inhibits glutathione S-transferase (GSTs) and Wnt signaling pathways, acts as a radiosensitizer, and can inhibit airway smooth muscle (ASM) contraction in mice. It can also increase the outflow of aqueous humor from the eye, supporting the study of glaucoma[1][2][3][4][5][6][7][8][9]. It is supplied as a white to off-white solid (C13H12Cl2O4, MW 303.14) at 99.90% purity.
Physical & Chemical Properties
| CAS Number | 58-54-8 |
|---|---|
| Molecular Formula | C13H12Cl2O4 |
| Molecular Weight | 303.14 g/mol |
| Purity | 99.90% |
| Appearance | Solid |
| Color | White to off-white |
| SMILES | O=C(O)COC1=CC=C(C(C(CC)=C)=O)C(Cl)=C1Cl |
| Target | L-type calcium channel |
| Signaling Pathway | Stem Cell/Wnt; Metabolic Enzyme/Protease; NF-κB; Neuronal Signaling; Membrane Transporter/Ion Channel; Immunology/Inflammation |
| Solubility | In Vitro: DMSO: 100 mg/mL (329.88 mM; Requires sonication; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) |
| Storage | 4°C, protect from light. In solvent: -80°C, 1 year; -20°C, 6 months (protect from light). |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
[7]. Harada T, et al. Ethacrynic acid decreases expression of proinflammatory intestinal wall cytokines and ameliorates gastrointestinal stasis in murine postoperative ileus. Clinics (Sao Paulo). 2018 Oct 18;73:e332.
[10].
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | 100 mg/mL (329.88 mM) | requires sonication; use freshly opened DMSO (absorbed moisture lowers solubility) |
Aliquot the stock solution and store it at -80°C (up to 1 year) or -20°C (up to 6 months); protect from light; avoid repeated freeze-thaw cycles.
In Vivo
Choose the formulation that suits the animal model and route of administration; percentages are volume ratios of the final working solution. Start from a clear DMSO stock (see In Vitro above), add the co-solvents one at a time in the order listed, mixing after each addition, and prepare the working solution fresh on the day of dosing. If precipitation or phase separation occurs, gentle warming or sonication can help.
Protocol 1
| Composition | 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% saline |
|---|---|
| Result | ≥ 2.5 mg/mL (8.25 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 2.5 mg/mL (saturation not determined). For 1 mL of working solution: add 100 μL DMSO stock (25.0 mg/mL) to 400 μL PEG300; then 50 μL Tween-80; then 450 μL saline to bring the volume to 1 mL. Saline: dissolve 0.9 g sodium chloride in ddH2O and make up to 100 mL. |
Protocol 2
| Composition | 10% DMSO + 90% (20% SBE-β-CD in saline) |
|---|---|
| Result | ≥ 2.5 mg/mL (8.25 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 2.5 mg/mL (saturation not determined). For 1 mL of working solution: add 100 μL DMSO stock (25.0 mg/mL) to 900 μL 20% SBE-β-CD in saline. 20% SBE-β-CD in saline: dissolve 2 g SBE-β-CD powder in 10 mL saline until clear (4°C, store up to one week). |
Protocol 3
| Composition | 10% DMSO + 90% Corn Oil |
|---|---|
| Result | ≥ 2.5 mg/mL (8.25 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 2.5 mg/mL (saturation not determined). Use with caution if continuous dosing will exceed two weeks. For 1 mL of working solution: add 100 μL DMSO stock (25.0 mg/mL) to 900 μL corn oil. |
Direct preparation of the working solution
These formulations are prepared directly, without a DMSO stock; use them promptly after preparation.
Protocol 4
| Composition | PBS |
|---|---|
| Result | 1 mg/mL (3.30 mM); clear solution; requires sonication |
Data provided by the manufacturer.
In Vitro
In CLL cells, Ethacrynic acid (50 μM; 24 h) blocks Wnt/β-catenin signaling[1]. Ethacrynic acid (1-100 μM; 48 h) is cytotoxic to CLL cells, with an IC50 of 8.56 μM[1]. In the eye, Ethacrynic acid (0.01-0.25 mmol/L; 30 min) acutely raises aqueous humor outflow facility, with the outflow rate rising from 28% to 105%[2]. Ethacrynic acid (10-100 μM; 30 min) can block LPS (100 ng/mL)-induced activation of the NF-κB pathway in RAW264.7 cells and shows anti-inflammatory activity[3]. After radiation exposure, Ethacrynic acid (20 μM/mL; 2 h) can raise radiation intensity in MCF-7 cancer cells[3]. Tracheal ring contraction induced by high -K+ (80 mmol/L) and by acetylcholine (ACh, 100 μmol/L) is dose-dependently inhibited by Ethacrynic acid (100 μmol/L; 62.5-250 min), with EC50 values of 40.28 μmol/L and 56.22 μmol/L, respectively[8]. The intracellular Ca2+ concentration induced by high -K+ and ACh is lowered by Ethacrynic acid (100 μmol/L; 500-2500 s) from 0.40 to 0.16 and from 0.50 to 0.39, respectively[8].
RT-PCR[1]
| Cell Line | Chronic lymphocytic leukemia (CLL) |
|---|---|
| Concentration | 1 μM, 10 μM, 100 μM |
| Incubation Time | 16 h |
| Result | Depressed the expression of LEF-1, Cyclin D1 and Fibronectin in a concentration-dependent manner.( LEF-1, cyclin D1 and fibronectin are established target genes of the Wnt/b-catenin pathway). |
Western Blot Analysis[3]
| Cell Line | RAW 264.7 |
|---|---|
| Concentration | 10 μM, 20 μM, 50 μM, 100 μM;Before LPS treatment (100 ng/mL; 1 h) |
| Incubation Time | 30 min |
| Result | Inhibited the expression of iNOS mRNA. Inhibited degradation of IκBα and IκBβ. |
In Vivo
Ethacrynic acid (450 μg/mouse; oral gavage; once daily for 60 days) can suppress tumor growth in mice[5].
| Animal Model | Myeloma Balb/c mice model[5] |
|---|---|
| Dosage | 450 μg/mouse |
| Administration | Oral gavage (p.o.); Once daily for 60 days. After BALB/c mice were injected subcutaneously with 5 × 105 MPC11 myeloma cells. |
| Result | Significantly inhibited tumor growth. |
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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