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Substance Name: Ethacrynic acid [USAN:USP]
RN: 58-54-8
UNII: M5DP350VZV
InChIKey: AVOLMBLBETYQHX-UHFFFAOYSA-N

Note

  • 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.

Molecular Formula

  • C13-H12-Cl2-O4

Molecular Weight

  • 303.1398
 

Classification Codes

  • Diuretic
  • Diuretics
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Natriuretic Agents

Names and Synonyms

Name of Substance

  • Etacrynic acid [INN]
  • Ethacrynic acid
  • Ethacrynic acid [USAN:USP]

MeSH Heading

  • Ethacrynic acid

Synonyms

  • (2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic acid
  • (2,3-Dichloro-4-(2-methylenebutyryl)phenoxy)acetic acid
  • (4-(2-Methylenebutyryl)-2,3-dichlorophenoxy)acetic acid
  • 2,3-Dichloro-4-(2-methylenebutyl)phenoxyacetic acid
  • 2,3-Dichloro-4-(2-methylenebutyryl)phenoxy acetic acid
  • Acetic acid, (2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy)-
  • Acetic acid, (2,3-dichloro-4-(2-methylenebutyryl)phenoxy)-
  • Acide etacrynique
  • Acide etacrynique [INN-French]
  • Acido etacrinico
  • Acido etacrinico [INN-Spanish]
  • Acidum etacrynicum
  • Acidum etacrynicum [INN-Latin]
  • BRN 1915060
  • CCRIS 4638
  • Crinuryl
  • Edecril
  • Edecrin
  • Edecrina
  • EINECS 200-384-1
  • Endecril
  • Etacrinic acid
  • Etacrynic acid
  • Etakrinic acid
  • Ethacrinique (acide)
  • Ethacrynate
  • Ethacrynic acid
  • Hidromedin
  • HSDB 2136
  • Hydromedin
  • Kyselina 4-(2-(1-butenyl)karbonyl)-2,3-dichlorfenoxyoctova
  • Kyselina 4-(2-(1-butenyl)karbonyl)-2,3-dichlorfenoxyoctova [Czech]
  • Kyselina ethakrynova
  • Kyselina ethakrynova [Czech]
  • Methylenebutyryl phenoxyacetic acid
  • Methylenebutyrylphenoxyacetic acid
  • Mingit
  • MK-595
  • NSC 624008
  • NSC 85791
  • Otacril
  • Reomax
  • Taladren
  • UNII-M5DP350VZV
  • Uregit

Systematic Names

  • Acetic acid, (2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy)-
  • Acetic acid, (2,3-dichloro-4-(2-methylenebutyryl)phenoxy)-
  • Etacrynic acid
  • Ethacrynic acid

Registry Numbers

CAS Registry Number

  • 58-54-8

FDA UNII

  • M5DP350VZV

Related Registry Number

  • 6500-81-8 (hydrochloride salt)

System Generated Number

  • 0000058548

Structure Descriptors

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

Smiles

CCC(=C)C(=O)c1ccc(OCC(=O)O)c(Cl)c1Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 14800ug/kg (14.8mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 411, 1968.
guinea pig LD50 oral 469mg/kg (469mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 411, 1968.
man TDLo oral 3mg/kg (3mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR		 Archives of Internal Medicine. Vol. 117, Pg. 715, 1966.
mouse LD50 intraperitoneal 160mg/kg (160mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 411, 1968.
mouse LD50 intravenous 176mg/kg (176mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 23, Pg. 438, 1964.
mouse LD50 oral 600mg/kg (600mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 775, 1979.
mouse LD50 subcutaneous 189mg/kg (189mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 411, 1968.
mouse LD50 unreported 600mg/kg (600mg/kg)   European Patent Application. Vol. #0016635,
rabbit LD50 intravenous 78300ug/kg (78.3mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 411, 1968.
rabbit LD50 oral 449mg/kg (449mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 411, 1968.
rat LD50 intraperitoneal 43mg/kg (43mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 2, Pg. 411, 1968.
rat LD50 oral 1gm/kg (1000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 775, 1979.
women TDLo intravenous 3mg/kg (3mg/kg) SENSE ORGANS AND SPECIAL SENSES: TINNITUS: EAR Archives of Internal Medicine. Vol. 117, Pg. 715, 1966.
women TDLo oral 4mg/kg (4mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR Archives of Internal Medicine. Vol. 117, Pg. 715, 1966.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 122.5 deg C   EXP
log P (octanol-water) 3.690 (none)   EST
Atmospheric OH Rate Constant 2.79E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.