Ethacrynic acid

Base Information

• Chemical Name: Ethacrynic acid
• CAS No.: 58-54-8
• Molecular Formula: C13H12 Cl2 O4
• Molecular Weight: 303.142
• Hs Code.: 2918992090
• European Community (EC) Number: 200-384-1
• NSC Number: 757026,624008,85791
• UNII: M5DP350VZV
• DSSTox Substance ID: DTXSID3025257
• Nikkaji Number: J4.399K
• Wikipedia: Etacrynic_acid
• Wikidata: Q418571
• NCI Thesaurus Code: C485
• RXCUI: 4109
• Pharos Ligand ID: HAS1D1PKN2HX
• Metabolomics Workbench ID: 43173
• ChEMBL ID: CHEMBL456
• Mol file: 58-54-8.mol

Synonyms:Acid, Etacrynic;Acid, Ethacrinic;Acid, Ethacrynic;Edecrin;Etacrynic Acid;Ethacrinic Acid;Ethacrynate Sodium;Ethacrynic Acid;Ethacrynic Acid, Sodium Salt;Hydromedin;Sodium, Ethacrynate

Chemical Property of Ethacrynic acid

Chemical Property:

• Appearance/Colour: White solid.
• Melting Point: 122
• Boiling Point: 480°Cat760mmHg
• PKA: 3.50(at 25℃)
• Flash Point: 244.1°C
• PSA: 63.60000
• Density: 1.35g/cm³
• LogP: 3.60570
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO: soluble20mg/mL, clear
• Water Solubility.: Soluble in ethanol, chloroform, ether, ammonia, carbonates, and methanol. Insoluble in water.
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 302.0112642
• Heavy Atom Count: 19
• Complexity: 370

Purity/Quality:

99%, ^*data from raw suppliers

Ethacrynic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=C)C(=O)C1=C(C(=C(C=C1)OCC(=O)O)Cl)Cl
• Recent ClinicalTrials: Ethacrynic Acid Elimination in Non-Muscle Invasive Bladder Cancer Patients Undergoing Transurethral Resection
• Recent EU Clinical Trials: STUDY PHASE III, RANDOMIZED, DOUBLE-BLIND CONTROLLED TO EVALUATE THE EFFECTIVENESS OF FUROSEMIDE IN CONTINUOUS INFUSION VS ethacrynic acid IN CONTINUOUS INFUSION IN CHILDREN SUBJECT TO A heart surgery of age LESS THAN 10 YEARS
• 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.
• Uses: A diuretic used to treat high blood pressure and swelling caused by congestive heart failure, liver failure and kidney failure. 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. Ethacrynic acid is used to inhibits symport of sodium, potassium, and chloride primarily in the ascending limb of Henle, but also in the proximal and distal tubules. This pharmacological action results in excretion of these ions, increased urinary output, and reduction in extracellular fluid. This compound has been classified as a loop or high ceiling diuretic.

Technology Process of Ethacrynic acid

There total 14 articles about Ethacrynic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.5%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + <2,3-dichloro-4-(1-oxobutyl)phenyloxy>acetic acid (1217-67-0) → ethacrynic acid (58-54-8)

Guidance literature:

With potassium carbonate; In ethanol; water; at 90 ℃; for 10h;

Reference yield: 60.1%

t-butylamine salt of ethacrynic acid → ethacrynic acid (58-54-8)

Guidance literature:

With hydrogenchloride; In water; ethyl acetate; at 30 ℃; for 0.5h; pH=2 - 3;

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2,3-Dichlor-4-butyryl-phenoxyessigsaeure-aethylester (2977-51-7) → ethacrynic acid (58-54-8)

Guidance literature:

formaldehyd; 2,3-Dichlor-4-butyryl-phenoxyessigsaeure-aethylester; With potassium carbonate;

With hydrogenchloride; water;

DOI:10.3390/molecules14010019

upstream raw materials:

2,3-dichloro-4-(2-methylenebutyryl)-phenol

formaldehyd

2,3-Dichlor-4-butyryl-phenoxyessigsaeure-aethylester

2',3'-dichloro-4'-hydroxybutyrophenone

Downstream raw materials:

{2,3-Dichloro-4-[2-methylene-1-(methylsulfanylthiocarbonyl-hydrazono)-butyl]-phenoxy}-acetic acid

<2,3-Dichlor-4-(2-ethyl-4-nitrovaleryl)phenoxy>essigsaeure

<2,3-Dichlor-4-(2-ethyl-4-nitrobutyryl)phenoxy>essigsaeure

2-[2-(4-Carboxymethoxy-2,3-dichloro-benzoyl)-butyl]-malonic acid diethyl ester

Refernces

• 1、 -. "Process for the Preparation of Ethacrynic Acid". . . Retrieved 2018/05/03.
• 2、 Lee, Keefe Guang Zhi,Babak, Maria V.,Weiss, Andrea,Dyson, Paul J.,Nowak-Sliwinska, Patrycja,Montagner, Diego,Ang, Wee Han. "Development of an Efficient Dual-Action GST-Inhibiting Anticancer Platinum(IV) Prodrug". . p. 1210 - 1217. Retrieved 2018/06/04.