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

• ChemBase编号: 779
• 分子式: C13H12Cl2O4
• 平均质量: 303.13798
• 单一同位素质量: 302.01126422
• SMILES: Clc1c(C(=O)C(=C)CC)ccc(OCC(=O)O)c1Cl
• Canonical SMILES: CCC(=C)C(=O)c1ccc(c(c1Cl)Cl)OCC(=O)O
• 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)
• InChIKey: AVOLMBLBETYQHX-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
• IUPAC传统名: ethacrynic acid
• 商标名: Crinuryl; Edecril; Edecrin; Edecrina; Endecril; Hidromedin; Hydromedin; Mingit; Otacril; Reomax; Taladren; Uregit
• 别名: (2,3-二氯-4-[2-亚甲基丁酰]苯氧基)乙酸; 利尿酸; 2-[2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy]acetic Acid; [4-(2-Methylenebutyryl)-2,3-dichlorophenoxy]acetic Acid; Crinuril; Edecril; Edecrin; Edecrina; Endecril; Hidromedin; Hydromedin; MK 595; Mingit; NSC 624008; NSC 85791; Otacril; Reomax; Taladren; Uregit; Ethacrynic acid; 2,3-Dichloro-4(2-methylene-butyryl)phenoxy] acetic acid; Methylenebutyrylphenoxyacetic acid; Etacrinic acid; Etacrynic acid; Etakrinic acid; Ethacrynate; Ethacryinic Acid; Ethacrynic acid

登记号

• CAS号: 58-54-8
• EC号: 200-384-1
• MDL号: MFCD00056693
• PubChem SID: 46507562; 160964242; 24894577
• PubChem CID: 3278

理论计算性质

JChem

• Acid pKa: 2.796934
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 1.0121546
• LogD (pH = 7.4): 0.16142255
• Log P: 3.655707
• 摩尔折射率: 72.224 cm^3
• 极化性: 28.149776 Å^3
• 极化表面积: 63.6 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.42
• LOG S: -4.19
• 溶解度: 1.94e-02 g/l

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: White Solid
• 熔点: 121-122; 124-126°C
• 疏水性(logP): 3.3

安全信息

• 保存条件: -20°C Freezer; Room Temperature (15-30°C)
• RTECS编号: AG6600000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 20/21/22-36/37/38; R:22
• 安全公开号: 26-36; S:36/37/39
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H312-H315-H319-H332-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 级别: analytical standard, for drug analysis

详细说明

MP Biomedicals - 02190203

Crystalline

DrugBank - DB00903

• Drug Groups: approved
• Description: A compound that 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. [PubChem]
• Indication: For the treatment of high blood pressure and edema caused by diseases like congestive heart failure, liver failure, and kidney failure.
• Pharmacology: Ethacrynic acid is a monosulfonamyl loop or high ceiling diuretic. Ethacrynic acid acts on the ascending limb of the loop of Henle and on the proximal and distal tubules. Urinary output is usually dose dependent and related to the magnitude of fluid accumulation. Water and electrolyte excretion may be increased several times over that observed with thiazide diuretics, since ethacrynic acid inhibits reabsorption of a much greater proportion of filtered sodium than most other diuretic agents. Therefore, ethacrynic acid is effective in many patients who have significant degrees of renal insufficiency. Ethacrynic acid has little or no effect on glomerular filtration or on renal blood flow, except following pronounced reductions in plasma volume when associated with rapid diuresis.
• Toxicity: Overdosage may lead to excessive diuresis with electrolyte depletion.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Onset of action is rapid, usually within 30 minutes after an oral dose of ethacrynic acid or within 5 minutes after an intravenous injection of ethacrynic acid.
• Protein Binding: > 98%
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - E676000

A diuretic used to treat high blood pressure and swelling caused by congestive heart failure, liver failure and kidney failure.

参考文献

• Beyer, et al.: J. Pharmacol. Exp. Ther., 147, 1 (1965)
• Kim., et al.: Am. J. Cardiol., 27, 407 (1965)
• Williamson, H.E., et al.: J. Clin. Pharmacol., 17, 663 (1965)