Ethacrynic acid
- CAS No.
- 58-54-8
- Chemical Name:
- Ethacrynic acid
- Synonyms
- ETACRYNIC ACID;edecrin;mingit;mk-595;reomax;uregit;edecril;otacril;endecril;edecrina
- CBNumber:
- CB8215310
- Molecular Formula:
- C13H12Cl2O4
- Molecular Weight:
- 303.14
- MOL File:
- 58-54-8.mol
- MSDS File:
- SDS
- Modify Date:
- 2023/9/4 15:51:00
| Melting point | 125 °C |
|---|---|
| Boiling point | 480.0±45.0 °C(Predicted) |
| Density | 1.3562 (estimate) |
| storage temp. | 2-8°C |
| solubility | DMSO: soluble20mg/mL, clear |
| form | powder |
| pka | 3.50(at 25℃) |
| color | white to beige |
| Water Solubility | Soluble in ethanol, chloroform, ether, ammonia, carbonates, and methanol. Insoluble in water. |
| Merck | 3717 |
| CAS DataBase Reference | 58-54-8(CAS DataBase Reference) |
| EPA Substance Registry System | Ethacrynic acid (58-54-8) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302+H312+H332-H315-H319-H335 | |||||||||
| Precautionary statements | P261-P280-P301+P312+P330-P305+P351+P338 | |||||||||
| Hazard Codes | Xn | |||||||||
| Risk Statements | 20/21/22-36/37/38 | |||||||||
| Safety Statements | 26-36 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | AG6600000 | |||||||||
| HS Code | 2918992090 | |||||||||
| Toxicity | LD50 in mice (mg/kg): 176 i.v.; 627 orally (Peck) | |||||||||
| NFPA 704 |
|
Ethacrynic acid Chemical Properties,Uses,Production
Description
Ethacrynic acid is a loop diuretic with anticancer activity., 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., 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. 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). Ethacrynic acid (250 μg per day) increases tumor growth reduction induced by the EGFR family inhibitors afatinib (Item Nos. 11492 | 21567) or neratinib in a 4T1 murine breast cancer model. Formulations containing ethacrynic acid have been used in the treatment of edema.
Chemical Properties
White Solid
Uses
Ethacrynic acid is a powerful diuretic prescribed for edema associated with cardiac insufficiency, renal edema that does not respond to other diuretics, and edema of the brain and lungs.
Definition
ChEBI: An aromatic ether that is phenoxyacetic acid in which the phenyl ring is substituted by chlorines at positions 2 and 3, and by a 2-methylidenebutanoyl group at position 4. It is a loop diuretic used to treat high blood pressure resulting from diseases such as congestive heart failure, liver failure, and kidney failure. It is also a glutathione S-transferase (EC 2.5.1.18) inhibitor.
General Description
White solid.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Ethacrynic acid may react vigorously with strong oxidizing agents. Can react exothermically with reducing agents (such as alkali metals and hydrides) to release gaseous hydrogen. May react exothermically with acids. Reacts exothermically with all bases both organic (for example, the amines) and inorganic.
Fire Hazard
Ethacrynic acid is probably combustible.
Mechanism of action
The mechanism of action of ethacrynic acid appears to be more complex than the simple addition of sulfhydryl groups of the enzyme to
the drug molecule. When the double bond of ethacrynic acid is reduced, the resultant compound is still active, although the diuretic activity is diminished. The sulfhydryl
groups of the enzyme would not be expected to add to the drug molecule in the absence of the α,β-unsaturated ketone.
These compounds are potent high-ceiling diuretics that resemble ethacrynic acid in their mechanism of action. The ethyl ester group represents a pro-drug that can be
easily hydrolyzed to the free carboxyl group. As in ethacrynic acid, a 2,3-dichloro substitution is necessary. In addition, a para-hydroxyl group and an unsubstituted
aminomethyl group on the benzene ring are highly beneficial. The carbonyl group can be replaced with an ether or sulfide group. These compounds have no ability to add
the sulfhydryl groups of the kidney enzymes. The complete mechanism of action of these compounds remains in doubt.
Ethacrynic acid Preparation Products And Raw materials
Raw materials
1of6
chevron_rightPreparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Solara Active Pharma Sciences Ltd | +91-8046632100 +91-7075706520 | Bangalore, India | 65 | 58 | Inquiry |
| Biophore India Pharmaceuticals Pvt Ltd | +91-9100031592 +91-9030907714 | Telangana, India | 134 | 58 | Inquiry |
| Mylan Laboratories Ltd | +91-4023550543 +91-4030866666 | Telangana, India | 150 | 58 | Inquiry |
| Apicore Pharmaceuticals Pvt Ltd | +91-2662267177 +91-2662267166 | Gujarat, India | 181 | 58 | Inquiry |
| Enaltec Labs Pvt Ltd | +91-9167119247 +91-9167119247 | Maharashtra, India | 49 | 58 | Inquiry |
| KARPSCHEM LABORATORIES | +91-7249203006 +91-7249203006 | Maharashtra, India | 786 | 58 | Inquiry |
| Synthink Research Chemicals | 09158051123 | Pune, India | 398 | 58 | Inquiry |
| Innorex Pharmaceuticals Private Limited | 91-22-28560031 | Maharashtra, India | 173 | 58 | Inquiry |
| KPS Chemicals & Pharmaceuticals | 91--8469484608 | Gujarat, India | 240 | 58 | Inquiry |
| EMCURE PHARMACEUTICALS LTD | +91 22 3061 0000 | New Delhi, India | 93 | 58 | Inquiry |
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