Ethacrynic Acid 利尿酸
CAS 58-54-8 MFCD00056693
化学结构图
SMILES: C=C(CC)C(=O)c1ccc(OCC(=O)O)c(Cl)c1Cl
化学属性
| Mol. Formula | C13H12Cl2O4 |
|---|---|
| Mol. Weight | 303.15 |
| Appearance | 白色结晶性粉末。熔点122℃。极易溶于乙醇，易溶于乙醚、氯仿或冰醋酸，不溶于水。 |
| Melting Point | 125 °C |
| Solubility | Soluble in ethanol, chloroform, ether, ammonia, carbonates, and methanol. Insoluble in water., Soluble in ethanol, chloroform, ether, ammonia, carbonates, and methanol. Insoluble in water. |
别名和识别编码
| Chemical Name | Ethacrynic Acid |
|---|---|
| CAS Number | 58-54-8 |
| Synonym | etakrinicacid Kyselina ethakrynova hydromedin edecril 2,3-二氯-4-(2-亚甲基丁酰)苯氧乙酸 Acetic acid, (2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy)- hidromedin Etacrinic acid ######## [2,3-Dichloro-4-(2-methylene-1-oxobutyl)phe-noxy]aceticacid Taladren methylenebutyrylphenoxyaceticacid Hyd (2,3-二氯-4-[2-亚甲基丁酰]苯氧基)乙酸;依他尼酸 Crinuryl (2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy)aceticacid Otacril 依他尼酸 kyselinaethakrynova (4-(2-Methylenebutyryl)-2,3-dichlorophenoxy)acetic acid Edecrina Methylenebutyryl phenoxyacetic acid etacrinicacid kyselina4-(2-(1-butenyl)karbonyl)-2,3-dichlorfenoxyoctova ETHACRYNIC ACID Etakrinic acid [2,3-DICHLORO-4-(2-METHYLENEBUTYRYL)PHENOXY]ACETIC ACID 利尿酸 Uregit MK-595 (2,3-二氯-4-[2-亚甲基丁酰]苯氧基)乙酸 (4-(2-methylenebutyryl)-2,3-dichlorophenoxy)aceticacid (2,3-dichloro-4-(2-methylenebutyryl)phenoxy)-aceticaci (2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy)-aceticaci Edecrin edecrin crinuryl ETACRYNIC ACID (2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic acid Edecril Hidromedin Kyselina 4-(2-(1-butenyl)karbonyl)-2,3-dichlorfenoxyoctova Reomax edecrina Ethacrynic acid 2,3-Dichloro-4-(2-methylenebutyryl)phenoxy acetic acid endecril (2,3-Dichloro-4-(2-methylenebutyryl)phenoxy)acetic acid Mingit Endecril 2-[2,3-Dichloro-4-(2-methylidenebutanoy |
| EC Number | 200-384-1 |
| MDL Number | MFCD00056693 |
| PubChem Substance ID | 3278 |
| Chemical Name Translation | 利尿酸 |
| Merck Number | 3717 |
| Wiswesser Line Notation | QV1OR BG CG DVY2&U1 |
| Beilstein Registry Number | 1915060 |
| LabNetwork Molecule ID | LN00198836 |
| InChI | 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) |
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专业采购外包团队在线服务
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分类
- Aromatics
- Pharmaceuticals
- Intermediates & Fine Chemicals
- {SNA} All Doping Standards (A-Z), Alphabetic, Analytical Standards, Analytical/Chromatography, Chromatography, Diuretic, Doping Substances, Drugs & Metabolites, E, EQ - EZ, Forensic and Veterinary Standards, Neat Compounds
产品应用
- A compound classified as a high ceiling diuretic
相关文献及参考
- [2]. 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.
- [3]. Zhao XX, et al. Ethacrynic acid inhibits airway smooth muscle contraction in mice. Sheng Li Xue Bao. 2019 Dec 25;71(6):863-873.
- [4]. Byun HJ, et al. Ethacrynic Acid Inhibits Sphingosylphosphorylcholine-Induced Keratin 8 Phosphorylation and Reorganization via Transglutaminase-2 Inhibition. Biomol Ther (Seoul). 2013 Sep 30;21(5):338-42.
- Beyer, et al.: J. Pharmacol. Exp. Ther., 147, 1 (1965),
- Kim., et al.: Am. J. Cardiol., 27, 407 (1971),
- Williamson, H.E., et al.: J. Clin. Pharmacol., 17, 663 (1977),
- [1]. Li XQ, et al. Metabolism of Strained Rings: Glutathione S-transferase-Catalyzed Formation of a Glutathione-Conjugated Spiro-azetidine without Prior Bioactivation. Drug Metab Dispos. 2019 Nov;47(11):1247-1256.
- {M
安全信息
- S36 Wear suitable protective clothing 穿戴适当的防护服；
- S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
- R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
- R20/21/22 Harmful by inhalation, in contact with skin and if swallowed 吸入、皮肤接触和不慎吞咽有害
GHS Symbol
- P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
- P305+P351+P338
- H332 Harmful if inhaled 吸入有害
- H315 Causes skin irritation 会刺激皮肤
- H302 Harmful if swallowed 吞食有害
- H312 Harmful in contact with skin 皮肤接触有害
- H335 May cause respiratory irritation 可能导致呼吸道刺激
- H319 Causes serious eye irritation 严重刺激眼睛
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human - woman DOSE/DURATION : 3 mg/kg TOXIC EFFECTS : Sense Organs and Special Senses (Ear) - tinnitus REFERENCE : AIMDAP Archives of Internal Medicine. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1908- Volume(issue)/page/year: 117,715,1966
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Unreported SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 600 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #0016635
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 189 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,411,1968
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - man DOSE/DURATION : 3 mg/kg TOXIC EFFECTS : Sense Organs and Special S
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 14800 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,41
其他信息
- 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.
- 上游原料:氢氧化钠 --> 盐酸 --> 甲醇 --> 乙醚 --> 硫酸 --> 乙酸 --> 硫酸钠 --> 碳酸氢钠 --> 苯 --> 三氯化铝 --> 无水醋酸钠 --> 二硫化碳 --> 多聚甲醛 --> 氯乙酸 --> 环己烷 --> 溴乙酸乙酯 --> 稀盐酸 --> 庚烷 --> 正丁酰氯 --> 活性碳 --> 盐酸二甲胺 --> 甲基环己烷 --> 2,3-二氯苯酚 --> 2,6-二氯苯甲醚 --> 苯丁酮 --> 苯氧乙酸乙酯 --> 2,3-二氯苯氧基乙酸
- MSDS 信息:2-[2,3-Dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid(58-54-8).msds
- Sigma Aldrich:58-54-8(sigmaaldrich)
- 方法一:由2，3-二氯苯甲醚与丁酰氯缩合，并水解为2，3-二氯-4-丁酰苯酚，再与溴乙酸乙酯缩合，然后进一步与甲醛缩合并水解为依他尼酸。1.2，3-二氯-4-丁酰苯酚的制备将丁酰氯、二氯本甲醚及三氯化铝依次加入二硫化碳中，室温下反应1h，再加流1h后，回收二硫化碳。回收毕，加入正庚烷，再加入三氯化铝，继续回流3h。冷至50℃，分去正庚烷，冷却，加稀盐酸，升温至86℃，立即冷至40℃，过滤、洗涤，得2，3-二氯-4-丁酰苯酚粗品。粗品用酸碱法精制、活性炭脱色，得熔点为108-111℃的精品。收率85%。2.依他尼酸的制备将2，3-二氯-4-丁酰苯酚、无水乙醇和乙酸钠加热至回流，滴加溴乙酸乙酯，反应3h后回收乙醇。冷却，过滤，洗涤，用乙醇重结晶，得2，3-二氯-4-丁酰苯氧乙酸乙酯。然后将其投入甲醛和乙醇的混合液中，于回流下滴加碳酸钾、水和乙醇的混合液，继续回流1.5h。冷却，加稀盐酸析出沉淀，过滤、洗涤、干燥，最后经重结晶和活性炭脱色而得依他尼酸。收率约40%。
- TCI Shanghai:利尿酸 Ethacrynic Acid,>;98.0%(T)(58-54-8)
- 用途一:该品为强利尿药。具有抑制肾小管对钠、氯离子的再吸收作用，作用强而快，是严重水肿所必需的药物，但毒性较大，慢性肾功能不全者少用。鼠口服LD50为627mg/kg。
- MOL 文件:58-54-8.mol
