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

• ChemBase ID: 779
• Molecular Formular: C13H12Cl2O4
• Molecular Mass: 303.13798
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
• IUPAC Traditional name: ethacrynic acid
• Brand Name: Crinuryl; Edecril; Edecrin; Edecrina; Endecril; Hidromedin; Hydromedin; Mingit; Otacril; Reomax; Taladren; Uregit
• Synonyms: 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; (2,3-二氯-4-[2-亚甲基丁酰]苯氧基)乙酸; 利尿酸

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.796934
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.0121546
• LogD (pH = 7.4): 0.16142255
• Log P: 3.655707
• Molar Refractivity: 72.224 cm^3
• Polarizability: 28.149776 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.42
• LOG S: -4.19
• Solubility (Water): 1.94e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 121-122; 124-126°C
• Hydrophobicity(logP): 3.3

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: AG6600000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38; R:22
• Safety Statements: 26-36; S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Grade: analytical standard, for drug analysis

DETAILS

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.

REFERENCES

• 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)