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Ethacrynic acid

Ethacrynic acid 구조식 이미지
카스 번호:
Ethacrynic acid
포뮬러 무게:
MOL 파일:

Ethacrynic acid 속성

125 °C
끓는 점
480.0±45.0 °C(Predicted)
1.3562 (estimate)
저장 조건
DMSO: soluble20mg/mL, clear
물리적 상태
산도 계수 (pKa)
3.50(at 25℃)
white to beige
Soluble in ethanol, chloroform, ether, ammonia, carbonates, and methanol. Insoluble in water.
CAS 데이터베이스
58-54-8(CAS DataBase Reference)
Ethacrynic acid (58-54-8)
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn
위험 카페고리 넘버 20/21/22-36/37/38
안전지침서 26-36
WGK 독일 3
RTECS 번호 AG6600000
HS 번호 2918992090
유해 물질 데이터 58-54-8(Hazardous Substances Data)
독성 LD50 in mice (mg/kg): 176 i.v.; 627 orally (Peck)
기존화학 물질 KE-10151
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P405 밀봉하여 저장하시오.

Ethacrynic acid MSDS

2-[2,3-Dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid

Ethacrynic acid C화학적 특성, 용도, 생산


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 (Item No. 18404) in a 4T1 murine breast cancer model. Formulations containing ethacrynic acid have been used in the treatment of edema.

화학적 성질

White Solid


Hydromedin,MSD,W. Germany,1966


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.


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 inhibitor.

Manufacturing Process

Step A: Preparation of 2,3-Dichloro-4-Butyrylphenoxy Acid - The product is prepared using the following ingredients: 22.1 grams (0.1 mol) 2,3- dichlorophenoxyacetic acid; 21.3 grams (0.2 mol) n-butyryl chloride; and 53.3 grams (0.4 mol) powdered aluminum chloride.
The 2,3-dichlorophenoxyacetic acid and n-butyryl chloride are placed in the reaction vessel and stirred while the aluminum chloride is added portionwise over a 45-minute period. The mixture then is heated on the steam bath for 3 hours and allowed to cool to room temperature. The gummy product obtained is added to a mixture of 300 ml of crushed ice and 30 ml concentrated hydrochloric acid. The resulting mixture is extracted with ether and the extract evaporated at reduced pressure. The residue is suspended in boiling water and dissolved by addition of a minimum quantity of 40% sodium hydroxide. After treatment with decolorizing charcoal and filtering, the hot filtrate is made acid to Congo red paper and chilled in ice.
The oil that separates is extracted with ether, the extract dried over anhydrous sodium sulfate and then evaporated at reduced pressure. The residue is dissolved in boiling benzene (75 ml) treated with decolorizing charcoal, filtered, treated with boiling cyclohexane (275 milliliters) and cooled to give 22.3 grams of 2,3-dichloro-4-butyrylphenoxyacetic acid. After several recrystallizations from a mixture of benzene and cyclohexane, then from methyl cyclohexane, next from a mixture of acetic acid and water, and finally from methylcyclohexane, the product melts at 110° to 111°C (corr).
Step B: Preparation of 2,3-Dichloro-4-[2-(Dimethylaminomethyl) Butyryl]Phenoxyacetic Acid Hydrochloride - In a 100 ml round flask equipped with an outlet tube suitable for application of intermittent suction, an intimate mixture of 5.20 grams (0.0179 mol) 2,3-dichloro-4-butyrylphenoxyacetic acid; 0.63 gram (0.0209 mol) paraformaldehyde; 1.59 grams (0.0195 mol) dry dimethylamine hydrochloride; and 4 drops acetic acid is heated on the steam bath for about 1.5 hours during which period suction is applied for about 1 minute intervals five or six times. Upon cooling, a solid is obtained, The crude reaction product is triturated with ether to give 5.8 grams (85%) of 2.3- dichloro-4-[2-dimethylaminomethyl)butyryl]phenoxyacetic acid hydrochloride in the form of a white solid. After two recrystallizations from a mixture of methanol and ether, the product melts at 165° to 167°C.
Step C: Preparation of 2,3-Dichloro-4-(2-Methylenebutyryl) Phenoxyacetic Acid - The Mannich compound obtained as described above is treated with aqueous sodium bicarbonate to form 2,3-dichloro-4-(2- methylenebutyryl)phenoxyacetic acid, MP 115° to 118°C. Two recrystallizations from a mixture of benzene and cyclohexane give white solid material melting at 118.5° to 120.5°C.


Edecrin (Merck).

Therapeutic Function

Diuretic, Cardiotonic, Smooth muscle relaxant, Respiratory stimulant

일반 설명

White solid.

공기와 물의 반응

Insoluble in water.

반응 프로필

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.


Ethacrynic acid is probably combustible.

Biochem/physiol Actions

Ethacrynic acid is non sulfonamide loop diuretic that is used to treat high blood pressure and the swelling caused by diseases like congestive heart failure. Ethacrynic acid blocks sodium-potassium-chloride cotransport. Also, Ethacrynic acid potently inhibits glutathione S-transferase family members. Studies show that ethacrynic acid potently inhibits Tgase-2 (transglutaminase-2) dependent metastasis of cancer cells including lung and pancreatic cancers.

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.

Chemical Synthesis

Ethacrynic acid—[2,3-dichloro-4-(2-methylenbutyryl)phenoxy]acetic acid (21.4.9), is synthesized from 2,3-dichlorophenoxyacetic acid. This is acylated with butyroyl chloride, forming 4-butyroyl-2,3-dichlorophenoxyacetic acid (21.4.7), which is further aminomethylated under Mannich reaction conditions using dimethylamine and formaldehyde. The resulting product (21.4.8) undergoes further thermal degredation, forming an unsaturated ketone—ethacrynic acid (21.4.9).

Veterinary Drugs and Treatments

Ethacrynic acid is a loop diuretic that shares the same indications as furosemide (congestive cardiomyopathy, pulmonary edema, hypercalcuric nephropathy, uremia, as adjunctive therapy in hyperkalemia and, occasionally, as an antihypertensive agent). Its use has been largely supplanted in the armamentarium by furosemide for these indications.
Ethacrynic acid may be useful in the treatment of nephrogenic diabetes insipidus as it may cause a paradoxical decrease in urine volume. Other uses include the adjunctive treatment of hypercalcemia and to increase the excretion of bromide in the treatment of bromide toxicity.

Ethacrynic acid 준비 용품 및 원자재


준비 용품

Ethacrynic acid 공급 업체

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