Etacrynsure

ETACRYNIC ACID · edecrin · mingit · mk-595 · reomax · uregit · edecril · otacril

Identifikatoren & physikalische Daten

CAS No.	58-54-8
Summenformel	C13H12Cl2O4
Durchschnittliche Molmasse	303,13 g/mol
Monoisotopische Masse	302,01126422 g/mol
SMILES	C=C(CC)C(=O)c1ccc(OCC(=O)O)c(Cl)c1Cl
InChIKey	AVOLMBLBETYQHX-UHFFFAOYSA-N
PubChem CID	3278
ChEMBL	CHEMBL456
ChEBI	CHEBI:4876
EC No.	200-384-1
DTXSID	DTXSID3025257
Lokaler Name	Etacrynsure

Chemische & physikalische Eigenschaften

XLogP	3,8
Polarare Oberfläche (TPSA)	63,6
H-Brücken-Donoren	1
H-Brücken-Akzeptoren	4
Frei drehbare Bindungen	6
Schwere Atome	19
Formalladung	0
Komplexität	370
Arzneimittel	Pharmaceuticals -> Listed in ZINC15
LogP (Verteilungskoeffizient)	3.3
Color/Form	CrystalsWhite, or practically white, crystalline powder
Löslichkeit	less than 1 mg/mL at 75 °F (NTP, 1992)Sparingly soluble in water, aq acidssoluble in chloroformVery slightly soluble in water but soluble in most organic solvents such as alcohols, chloroform, and benzene1.94e-02 g/LDMSO: soluble20mg/mL, clearSoluble in ethanol, chloroform, ether, ammonia, carbonates, and methanol. Insoluble in water.
Human Drugs	Breast FeedingLactationAntihypertensive AgentsLoop DiureticsFDA approved drugs -> Active ingredientPharmaceuticals
Endocrine Disruptors	Potential endocrine disrupting compound
Decomposition	When heated to decomp it emits toxic fumes of /hydrogen chloride/.
Schmelzpunkt	252 °F (NTP, 1992)118.5-120.5121-122 °C122.5 °C125 °C
Physical Description	Ethacrynic acid is a white solid. (NTP, 1992)
Stability/Shelf Life	Solns at pH 7 at 25 °C stable for short periods of time. Stability decreased with an incr in pH, temp and time. /sodium salt/This compound is stable under normal laboratory conditions.
Dissociation Constants	3.53.1pKa'= 3.50
Other Experimental Properties	UV max (water): 225 nm(E=15287)Soluble in water at 25 °C: up to 9%Solutions at pH 7 @ 25 °C stable for short periods of time. Stability decreased with increase in pH, temperature, and time. /Ethacrynate sodium/Soluble in water @ 25 °C to the extent of about 7%solutions of the sodium salt are relatively stable at pH 7 at room temperature for short periods but as the pH or temperature increase solutions are less stable /Ethacrynate sodium/
Siedepunkt	480.0±45.0 °C(Predicted)
Dichte	1.3562 (estimate)
Lagerbedingungen	2-8°C
Aggregatzustand	powder
pKa (Säurekonstante)	3.50(at 25℃)
Farbe	white to beige
Merck	3717
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)
InChIKey	AVOLMBLBETYQHX-UHFFFAOYSA-N
SMILES	ClC1=C(Cl)C(C(C(CC)=C)=O)=CC=C1OCC(O)=O
CAS Datenbank	58-54-8(CAS DataBase Reference)
EPA chemische Informationen	Ethacrynic acid (58-54-8)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Weitere Sicherheitsinformationen	IMAP assessments - Acetic acid, [2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]-: Human health tier I assessment
Brandgefahren	This chemical is probably combustible. (NTP, 1992)
Brandpotenzial	The flash point of this chemical is not available, but it is probably combustible.
Gesundheitsgefahren	SYMPTOMS: Symptoms associated with exposure to this chemical may include fluid and electrolyte imbalances, gout, gastrointestinal disturbances, depression of formed elements of the blood, skin rashes, paresthesias and hepatic dysfunction. It may also cause transient or permanent deafness in rare cases.
FDA-Anforderungen	The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl ethacrynic acid, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Reaktive Gruppe	Acids, Carboxylic
Special Reports	JONES HCINTRAUTERINE OTOTOXICITY CASE REPORT AND REVIEW OF LITERATUREJ NATL MED ASSOC 65: 201 (1973) INTRAUTERINE OTOTOXICITY & REVIEW OF LITERATURE, INCLUDING ETHACRYNIC ACID IS DISCUSSED.RAHN KHCLINICAL PHARMACOLOGY OF DIURETICSCLIN EXP HYPERTENS (A) 5(2): 157 (1983) A REVIEW OF THE CLINICAL PHARMACOLOGY OF DIURETICS, INCLUDING PHARMACODYNAMIC DRUG INTERACTIONS WITH DIURETICS.KOECHEL DAETHACRYNIC ACID AND RELATED DIURETICS: RELATIONSHIP OF STRUCTURE TO BENEFICIAL AND DETRIMENTAL ACTIONSANNU REV PHARMACOL TOXICOL 21: 265 (1981) A REVIEW WITH 186 REFERENCES ON THE BENEFICIAL & DETRIMENTAL EFFECTS OF PHENOXYACETIC ACID-TYPE DIURETICS SUCH AS ETHACRYNIC ACID.

Anwendungen & Verwendung

Beschreibung

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.

Verwenden

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.