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Chemistry

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Also known as: Etacrynic acid, 58-54-8, Ethacrynate, Edecrin, Etacrinic acid, Hydromedin

Molecular Formula

C₁₃H₁₂Cl₂O₄

Molecular Weight

303.13 g/mol

InChI Key

AVOLMBLBETYQHX-UHFFFAOYSA-N

FDA UNII

M5DP350VZV

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.

Ethacrynic acid is a Loop Diuretic. The physiologic effect of ethacrynic acid is by means of Increased Diuresis at Loop of Henle.

1 2D Structure

Ethacrynic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 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)

2.1.3 InChI Key

AVOLMBLBETYQHX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCC(=C)C(=O)C1=C(C(=C(C=C1)OCC(=O)O)Cl)Cl

2.2 Other Identifiers

2.2.1 UNII

M5DP350VZV

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acid, Etacrynic

2. Acid, Ethacrinic

3. Acid, Ethacrynic

4. Edecrin

5. Etacrynic Acid

6. Ethacrinic Acid

7. Ethacrynate Sodium

8. Ethacrynic Acid, Sodium Salt

9. Hydromedin

10. Sodium, Ethacrynate

2.3.2 Depositor-Supplied Synonyms

1. Etacrynic Acid

2. 58-54-8

3. Ethacrynate

4. Edecrin

5. Etacrinic Acid

6. Hydromedin

7. Taladren

8. Crinuryl

9. Edecril

10. Edecrina

11. Endecril

12. Hidromedin

13. Otacril

14. Mingit

15. Reomax

16. Uregit

17. Etakrinic Acid

18. Methylenebutyrylphenoxyacetic Acid

19. Mk-595

20. Ethacrinique (acide)

21. Acido Etacrinico

22. Acide Etacrynique

23. Acidum Etacrynicum

24. Kyselina Ethakrynova

25. Kyselina Ethakrynova [czech]

26. 2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic Acid

27. Acide Etacrynique [inn-french]

28. Acido Etacrinico [inn-spanish]

29. Acidum Etacrynicum [inn-latin]

30. (2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic Acid

31. Methylenebutyryl Phenoxyacetic Acid

32. [2,3-dichloro-4-(2-methylenebutyryl)phenoxy]acetic Acid

33. 2,3-dichloro-4-(2-methylenebutyl)phenoxyacetic Acid

34. Mk 595

35. Nsc 85791

36. (2,3-dichloro-4-(2-methylenebutyryl)phenoxy)acetic Acid

37. Nsc 624008

38. Brn 1915060

39. Acetic Acid, (2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy)-

40. Etacrynic Acid [inn]

41. 2,3-dichloro-4-(2-methylenebutyryl)phenoxy Acetic Acid

42. (4-(2-methylenebutyryl)-2,3-dichlorophenoxy)acetic Acid

43. 2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetic Acid

44. Nsc-85791

45. Chembl456

46. Nsc-624008

47. Acetic Acid, [2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]-

48. Kyselina 4-(2-(1-butenyl)karbonyl)-2,3-dichlorfenoxyoctova [czech]

49. M5dp350vzv

50. 58-54-8 (free Acid)

51. Mls000069535

52. Mls002701928

53. Chebi:4876

54. [2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic Acid

55. Kyselina 4-(2-(1-butenyl)karbonyl)-2,3-dichlorfenoxyoctova

56. Acetic Acid, (2,3-dichloro-4-(2-methylenebutyryl)phenoxy)-

57. Nsc85791

58. Nsc624008

59. Cas-58-54-8

60. [2,3-dichloro-4-(2-methylenebutanoyl)phenoxy]acetic Acid

61. [4-(2-methylenebutyryl)-2,3-dichlorophenoxy]acetic Acid

62. Ncgc00016260-05

63. 2-[2,3-dichloro-4-(2-methylenebutanoyl)phenoxy]acetic Acid

64. Smr000058600

65. [2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]acetic Acid

66. Ethacryinic Acid

67. Dsstox_cid_5257

68. Dsstox_rid_77718

69. Dsstox_gsid_25257

70. Ethacrynic Acid [usan:ban]

71. Ccris 4638

72. Hsdb 2136

73. Ethacrynic Acid (usp)

74. Sr-01000003010

75. Einecs 200-384-1

76. Unii-m5dp350vzv

77. Etacrynicacid

78. Etacrynsaure

79. Crinuril

80. Acetic Acid, [2,3-dichloro-4-(2-methylenebutyryl)phenoxy]-

81. Etacrynic-acid

82. Ethacrynic Acid [usan:usp]

83. 1gsf

84. 2gss

85. Prestwick_671

86. Opera_id_61

87. Spectrum_000813

88. Prestwick0_000259

89. Prestwick1_000259

90. Prestwick2_000259

91. Prestwick3_000259

92. Spectrum2_000097

93. Spectrum3_000425

94. Spectrum4_000544

95. Spectrum5_000680

96. E0526

97. Bmse000134

98. Schembl26353

99. Bspbio_000078

100. Bspbio_002010

101. Etacrynic Acid [jan]

102. Ethacrynic Acid [mi]

103. Kbiogr_001207

104. Kbioss_001293

105. Mls002548854

106. Divk1c_000900

107. Etacrynic Acid (jp17/inn)

108. Spectrum1500287

109. Spbio_000054

110. Spbio_002297

111. Ethacrynic Acid [hsdb]

112. Ethacrynic Acid [usan]

113. 2,3-dichloro-4-(2-methylenebutyryl)phenoxyacetic Acid

114. Bpbio1_000086

115. Gtpl7179

116. Zinc1382

117. Etacrynic Acid [mart.]

118. Ethacrynic Acid [vandf]

119. Dtxsid3025257

120. Etacrynic Acid [who-dd]

121. Hms502m22

122. Kbio1_000900

123. Kbio2_001293

124. Kbio2_003861

125. Kbio2_006429

126. Kbio3_001230

127. Ninds_000900

128. Hms1568d20

129. Hms1920m16

130. Hms2089n17

131. Hms2091d17

132. Hms2095d20

133. Hms3259g03

134. Hms3712d20

135. Pharmakon1600-01500287

136. Hy-b1640

137. Ethacrynic Acid, >=97% (hplc)

138. Tox21_110335

139. Tox21_201102

140. Bdbm50186231

141. Ccg-38915

142. Etacrynic Acid [ep Impurity]

143. Mfcd00056693

144. Nsc757026

145. S5561

146. Wln: Qv1or Bg Cg Dvy2&u1

147. Etacrynic Acid [ep Monograph]

148. Ethacrynic Acid [orange Book]

149. Gst Inhibitor-2 (ethacrynic Acid))

150. Akos003404732

151. Tox21_110335_1

152. Db00903

153. Ethacrynic Acid [usp Monograph]

154. Ks-1453

155. Nc00450

156. Nsc-757026

157. Idi1_000900

158. Ncgc00016260-01

159. Ncgc00016260-02

160. Ncgc00016260-03

161. Ncgc00016260-04

162. Ncgc00016260-06

163. Ncgc00016260-07

164. Ncgc00016260-08

165. Ncgc00016260-09

166. Ncgc00016260-10

167. Ncgc00016260-11

168. Ncgc00016260-13

169. Ncgc00022601-03

170. Ncgc00022601-04

171. Ncgc00022601-05

172. Ncgc00258654-01

173. Nci60_041898

174. Sbi-0051374.p003

175. Db-053221

176. Ab00051988

177. Cs-0013591

178. A51097

179. D00313

180. Ab00051988-19

181. Ab00051988_20

182. A831918

183. Q418571

184. Sr-01000003010-2

185. Sr-01000003010-3

186. Brd-k63630713-001-05-0

187. Brd-k63630713-001-15-9

188. [2,3-dichloro-4-(2-ethylacryloyl)phenoxy]acetic Acid #

189. Acetic Acid,3-dichloro-4-(2-methylenebutyryl)phenoxy]-

190. 2,3-dichloro-4-(2-methylenebutyryl)phenoxy)acetate

191. 4-(methylenebutyryl)-2,3-dichlorophenoxy)acetic Acid

192. Acetic Acid,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]-

193. Ethacrynic Acid, European Pharmacopoeia (ep) Reference Standard

194. Ethacrynic Acid, United States Pharmacopeia (usp) Reference Standard

195. 2-(2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic Acid

196. Etacrynic Acid For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₂Cl₂O₄
Molecular Weight	303.13 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	302.0112642 g/mol
Monoisotopic Mass	302.0112642 g/mol
Topological Polar Surface Area	63.6 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	370
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Edecrin
PubMed Health	Ethacrynic Acid (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	Ethacrynic acid is an unsaturated ketone derivative of an aryloxyace -tic acid. It is designated chemically as [2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy] acetic acid, and has a molecular weight of 303.14. Ethacrynic acid is a white, or practica...
Active Ingredient	Ethacrynate sodium; Ethacrynic acid
Dosage Form	Injectable; Tablet
Route	Injection; Oral
Strength	25mg; eq 50mg base/vial
Market Status	Prescription
Company	Aton

2 of 2
Drug Name	Edecrin
PubMed Health	Ethacrynic Acid (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	Ethacrynic acid is an unsaturated ketone derivative of an aryloxyace -tic acid. It is designated chemically as [2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy] acetic acid, and has a molecular weight of 303.14. Ethacrynic acid is a white, or practica...
Active Ingredient	Ethacrynate sodium; Ethacrynic acid
Dosage Form	Injectable; Tablet
Route	Injection; Oral
Strength	25mg; eq 50mg base/vial
Market Status	Prescription
Company	Aton

4.2 Therapeutic Uses

Diuretics

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

A major use of loop diuretics is in the treatment of acute pulmonary edema. A rapid incr in venous capacitance in conjunction with a brisk natriuresis reduces left ventricular filling pressures and thereby rapidly relieves pulmonary edema. Loop diuretics also are widely used for the treatment of chronic congestive heart failure when diminution of extracellular fluid volume is desirable to minimize venous and pulmonary congestion. Diuretics are widely used for the treatment of hypertension, and controlled clinical trials demonstrating reduced morbidity and mortality have been conducted with Na+-Cl- symport (thiazides and thiazide-like diuretics), but not Na+-K+-2Cl- symport, inhibitors. Nonetheless, Na+-K+-2Cl- symport inhibitors appear to lower blood pressure as effectively as Na+-Cl- symport inhibitors while causing smaller perturbations in the lipid profile. /Loop diuretics/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 773

The edema of nephrotic syndrome often is refractory to other classes of diuretics, and loop diuretics often are the only drugs capable of reducing the massive edema associated with this renal disease. Loop diuretics also are employed in the treatment of edema and ascites of liver cirrhosis; however, care must be taken not to induce encephalopathy or hepatorenal syndrome. In patients with a drug overdose, loop diuretics can be used to induce a forced diuresis to facilitate more rapid renal elimination of the offending drug. /Loop diuretics/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 773

Loop diuretics- combined with isotonic saline admin to prevent volume depletion- are used to treat hypercalcemia. Loop diuretics interfere with the kidney's ability to produce a concentrated urine. Consequently, loop diuretics combined with hypertonic saline are useful for the treatment of life-threatening hyponatremia. /Loop diuretics/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 773

For more Therapeutic Uses (Complete) data for ETHACRYNIC ACID (10 total), please visit the HSDB record page.

4.3 Drug Warning

Vet: Rapid ototoxicity in cats. Do not admin in cases of decr renal function.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 203

Not recommended for routine use /in pregnancy/. /Loop diuretics/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1230

Geriatric patients may be more sensitive to the effects of the usual adult dose.

Ethacrynic acid may cause adverse GI effects, including anorexia, abdominal discomfort or pain, nausea, vomiting, malaise, diarrhea, and dysphagia. Adverse GI effects occur most frequently when large doses are employed or after 1-3 months of continuous therapy and may necessitate discontinuing the drug. Severe, profuse, watery diarrhea may occur; the drug should be permanently discontinued if this occurs. GI bleeding has been reported, most frequently in patients receiving IV ethacrynate sodium therapy and especially in patients receiving heparin sodium concomitiantly. Acute necrotizing pancreatitis, with an incr in serum amylase, has been reported.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 2564

For more Drug Warnings (Complete) data for ETHACRYNIC ACID (16 total), please visit the HSDB record page.

4.4 Drug Indication

For the treatment of high blood pressure and edema caused by diseases like congestive heart failure, liver failure, and kidney failure.

FDA Label

5 Pharmacology and Biochemistry

5.1 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.

5.2 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

Diuretics

Agents that promote the excretion of urine through their effects on kidney function. (See all compounds classified as Diuretics.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

ETHACRYNIC ACID

5.3.2 FDA UNII

M5DP350VZV

5.3.3 Pharmacological Classes

Loop Diuretic [EPC]; Increased Diuresis at Loop of Henle [PE]

5.4 ATC Code

C - Cardiovascular system

C03 - Diuretics

C03C - High-ceiling diuretics

C03CC - Aryloxyacetic acid derivatives

C03CC01 - Etacrynic acid

5.5 Absorption, Distribution and Excretion

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.

Thirty-five % or less of ethacrynic acid was excreted in urine of rats and dogs, regardless of mode of admin and 50% or more appeared in feces, suggesting hepatic elimination of the drug.

PMID:4427293 Klaasen CD, Fitzgerald TJ; J Pharmacol Exp Ther 191: 548 (1974)

Renal elimination (67%), biliary/fecal (33%), 20% unchanged. /From table/

Ford MD, Delaney KA, Ling LJ, Erickson T; Clinical Toxicology. W.B. Saunders Company., Philadelphia, PA. 2001, p. 398

Ethacrynic acid is rapidly absorbed from the GI tract. Following oral admin, the diuretic effect occurs within 30 min and reaches a peak in approx 2 hr. The duration of action following oral admin is usually 6-8 hr but may continue up to 12 hr. Following IV admin of ethacrynate sodium, diuresis usually occurs within 5 min, reached a max within 15-30 min, and persists for approx 2 hr. In animals, substantial quantities of ethacrynic acid accumulate only in the liver. The drug does not enter the CSF. It is not known whether ethacrynic acid crosses the placenta or is distributed into milk in humans. ... Approx 30-65% of an IV dose of ethacrynate sodium is secreted by the proximal renal tubules and is excreted in urine; approx 35-40% is excreted in bile, partially as the cysteine conjugate. In dogs, approx 30-40% of the drug excreted in urine is unchanged, 20-30% is the cysteine conjugate, and 33-40% is an unstable, unidentified compound. The rate of urinary excretion of ethacrynic acid increases as urinary pH increases and is decreased by probenecid.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 2566

5.6 Metabolism/Metabolites

Hepatic.

After iv admin (5 or 50 mg/kg) of (14)C-ethacrynic acid to rats 60-70% was excreted into bile within 4 hr; <25% was ethacrynic acid, the remainder was biotransformation products. The 2 major metabolites in bile were identified; one was the glutathione adduct (ethacrynic acid-GSH) and the other was ethacrynic acid-mercapturate. Approx 40% of either dose was excreted as ethacrynic acid-GSH. Ethacrynic acid-mercapturate accounted for 18% of the low dose and 30% of the high dose excreted into bile. Dogs given a 5 mg/kg dose (iv) excreted 25, 11, and 9% of the dose as ethacrynic acid-mercapturate, ethacrynic acid-cysteine and ethacrynic acid-GSH, respectively.

PMID:4427293 Klaasen CD, Fitzgerald TJ; J Pharmacol Exp Ther 191: 548 (1974)

Animal studies indicate that ethacrynic acid is metabolized to a cysteine conjugate (which may contribute to the pharmacologic effects of the drug) and to an unstable, unidentified compound.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 2566

5.7 Mechanism of Action

Ethacrynic acid 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. Diuretics also lower blood pressure initially by reducing plasma and extracellular fluid volume; cardiac output also decreases, explaining its antihypertensive action. Eventually, cardiac output returns to normal with an accompanying decrease in peripheral resistance. Its mode of action does not involve carbonic anhydrase inhibition.

Optimal diuretic activity depends on at least 2 structural requirements: (1) methylene and adjacent ketone groups capable of reacting with sulfhydryl radicals of presumed receptor, and (2) substituents on aromatic nucleus.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 903

In vitro, ethacrynic acid inhibits the active transport of chloride in the lumen of the ascending limb of the loop of Henle, thereby diminishing reabsorption of sodium and chloride at that site. Because this inhibition occurred with lower concns of ethacrynic acid in the presence of cysteine, it has been proposed that the ethacrynate-cysteine metabolite is the most active form of the drug. The drug increases potassium excretion in the distal renal tubule. Ethacrynic acid does not inhibit carbonic anhydrase, and it is not an aldosterone antagonist. Aldosterone secretion may incr during therapy with the drug and may contribute to the hypokalemia caused by ethacrynic acid.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 2565

...IRREVERSIBLY COMBINES WITH 2 THIOL GROUPS OF GLYCERALDEHYDE 3-PHOSPHATE DEHYDROGENASE, THUS INACTIVATING THE ENZYME. HOWEVER, IT IS NOT POSSIBLE TO ATTRIBUTE DIURETIC ACTION TO THIS TYPE OF BIOCHEMICAL REACTION...

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 905

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API Reference Price

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D6 & D8, SY.NO. 234\/2,234\/3, ,235\/2 & 542\/2, IKP KNOWLEDGE PARK,","city":"TURKAPALLY-V SHAMIRPET HYDERABAD,TE","supplier":"THE U.S. PHARMACOPEIAL ","supplierCountry":"INDIA","foreign_port":"NA","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.0002","unit":"KGS","unitRateFc":"1260000","totalValueFC":"265.5","currency":"USD","unitRateINR":"98876750","date":"13-Nov-2021","totalValueINR":"19775.35","totalValueInUsd":"265.5","indian_port":"HYDERABAD AIR","hs_no":"29189990","bill_no":"6233778","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"P.NO. D6 & D8, SY.NO. 234\/2,234\/3, ,235\/2 & 542\/2, IKP KNOWLEDGE PARK,"}]