ethacrynic acid Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
diuretics, etacrynic acid derivatives 1071 58-54-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • sodium ethacrynate
  • ethacrynic acid
  • etacrynic acid
  • ethacrynate
  • ethacrynate sodium
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 weight: 303.14
  • Formula: C13H12Cl2O4
  • CLOGP: 3.44
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 63.60
  • ALOGS: -4.19
  • ROTB: 6

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
50 mg O
50 mg P

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 4.71 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.26 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 8.70 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 10, 1967 FDA ATON

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC C03CC01 CARDIOVASCULAR SYSTEM
DIURETICS
HIGH-CEILING DIURETICS
Aryloxyacetic acid derivatives
FDA PE N0000175366 Increased Diuresis at Loop of Henle
FDA EPC N0000175590 Loop Diuretic
CHEBI has role CHEBI:50184 ion-transport inhibitors
CHEBI has role CHEBI:76797 glutathione transferase (ec 2.5.1.18) inhibitors
CHEBI has role CHEBI:77608 loop diuretics
MeSH PA D004232 Diuretics
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D045283 Natriuretic Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Edema indication 267038008
Pulmonary Edema due to Chronic Heart Failure indication
Peripheral Edema due to Chronic Heart Failure indication
Hypertensive disorder off-label use 38341003 DOID:10763
Hypercalcemia off-label use 66931009 DOID:12678
Anuria contraindication 2472002 DOID:2983
Ototoxicity contraindication 9062008
Tetany contraindication 10629009
Poisoning by digitalis glycoside contraindication 12876009
Cirrhosis of liver contraindication 19943007 DOID:5082
Orthostatic hypotension contraindication 28651003
Dehydration contraindication 34095006
Hyperuricemia contraindication 35885006 DOID:1920
Hypokalemia contraindication 43339004
Low blood pressure contraindication 45007003
Acute nephropathy contraindication 58574008
Hypochloremic alkalosis contraindication 70134007
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Oliguria contraindication 83128009
Hyponatremia contraindication 89627008
Gout contraindication 90560007 DOID:13189
Hearing disorder contraindication 128540005
Liver function tests abnormal contraindication 166603001
Hypomagnesemia contraindication 190855004
Acute pancreatitis contraindication 197456007 DOID:2913
Thromboembolic disorder contraindication 371039008
Severe diarrhea contraindication 409587002
Azotemia contraindication 445009001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.19 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Solute carrier family 12 member 1 Transporter INHIBITOR WOMBAT-PK CHEMBL
Glutathione S-transferase P Enzyme IC50 5.47 CHEMBL
UDP-glucose 4-epimerase Enzyme IC50 4.85 CHEMBL
Glutathione S-transferase A1 Enzyme IC50 5.30 CHEMBL
Aldose reductase Enzyme IC50 5.94 DRUG MATRIX

External reference:

IDSource
4017934 VUID
N0000178920 NUI
D00313 KEGG_DRUG
6500-81-8 SECONDARY_CAS_RN
4017933 VANDF
4017934 VANDF
C0014963 UMLSCUI
CHEBI:4876 CHEBI
EAA PDB_CHEM_ID
CHEMBL456 ChEMBL_ID
CHEMBL1200487 ChEMBL_ID
DB00903 DRUGBANK_ID
D004976 MESH_DESCRIPTOR_UI
3278 PUBCHEM_CID
7179 IUPHAR_LIGAND_ID
1651 INN_ID
K41MYV7MPM UNII
4108 RXNORM
235337 MMSL
242311 MMSL
4690 MMSL
4691 MMSL
d00649 MMSL
002305 NDDF
002306 NDDF
373536004 SNOMEDCT_US
75341007 SNOMEDCT_US
81947000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Ethacrynic Acid HUMAN PRESCRIPTION DRUG LABEL 1 0054-0415 TABLET 25 mg ORAL ANDA 11 sections
Ethacrynic Acid HUMAN PRESCRIPTION DRUG LABEL 1 0832-1690 TABLET 25 mg ORAL ANDA 22 sections
Sodium Edecrin HUMAN PRESCRIPTION DRUG LABEL 1 25010-210 POWDER, FOR SOLUTION 50 mg INTRAVENOUS NDA 23 sections
Sodium Edecrin HUMAN PRESCRIPTION DRUG LABEL 1 25010-210 POWDER, FOR SOLUTION 50 mg INTRAVENOUS NDA 23 sections
EDECRIN HUMAN PRESCRIPTION DRUG LABEL 1 25010-215 TABLET 25 mg ORAL NDA 22 sections
ETHACRYNULLTE SODIUM HUMAN PRESCRIPTION DRUG LABEL 1 42023-157 INJECTION, POWDER, FOR SOLUTION 50 mg INTRAVENOUS ANDA 23 sections
ETHACRYNULLTE SODIUM HUMAN PRESCRIPTION DRUG LABEL 1 42023-157 INJECTION, POWDER, FOR SOLUTION 50 mg INTRAVENOUS ANDA 23 sections
ETHACRYNULLTE SODIUM HUMAN PRESCRIPTION DRUG LABEL 1 42023-157 INJECTION, POWDER, FOR SOLUTION 50 mg INTRAVENOUS ANDA 23 sections
Ethacrynic Acid HUMAN PRESCRIPTION DRUG LABEL 1 42799-405 TABLET 25 mg ORAL ANDA 23 sections
Ethacrynic acid HUMAN PRESCRIPTION DRUG LABEL 1 47781-497 TABLET 25 mg ORAL ANDA 22 sections
Ethacrynic Acid HUMAN PRESCRIPTION DRUG LABEL 1 49884-276 TABLET 25 mg ORAL ANDA 19 sections
Ethacrynic Acid HUMAN PRESCRIPTION DRUG LABEL 1 50228-334 TABLET 25 mg ORAL ANDA 22 sections
Ethacrynic acid Human Prescription Drug Label 1 52817-367 TABLET 25 mg ORAL ANDA 20 sections
Ethacrynic Acid HUMAN PRESCRIPTION DRUG LABEL 1 60429-887 TABLET 25 mg ORAL ANDA 12 sections
ETHACRYNIC ACID HUMAN PRESCRIPTION DRUG LABEL 1 64380-909 TABLET 25 mg ORAL ANDA 18 sections
Ethacrynic Sodium HUMAN PRESCRIPTION DRUG LABEL 1 67457-297 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 21 sections
Ethacrynic Acid HUMAN PRESCRIPTION DRUG LABEL 1 68180-159 TABLET 25 mg ORAL ANDA 12 sections
Ethacrynate Sodium HUMAN PRESCRIPTION DRUG LABEL 1 68382-246 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 18 sections
ethacrynic acid HUMAN PRESCRIPTION DRUG LABEL 1 68682-011 TABLET 25 mg ORAL NDA authorized generic 20 sections
ethacrynic sodium HUMAN PRESCRIPTION DRUG LABEL 1 68682-012 POWDER, FOR SOLUTION 50 mg INTRAVENOUS NDA authorized generic 20 sections
ethacrynic sodium HUMAN PRESCRIPTION DRUG LABEL 1 68682-012 POWDER, FOR SOLUTION 50 mg INTRAVENOUS NDA authorized generic 20 sections
EDECRIN HUMAN PRESCRIPTION DRUG LABEL 1 69189-0371 TABLET 25 mg ORAL NDA 23 sections
Ethacrynic Acid HUMAN PRESCRIPTION DRUG LABEL 1 69238-1126 TABLET 25 mg ORAL ANDA 19 sections
ETHACRYNULLTE SODIUM HUMAN PRESCRIPTION DRUG LABEL 1 69315-701 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 20 sections
Ethacrynate Sodium HUMAN PRESCRIPTION DRUG LABEL 1 70771-1106 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 50 mg INTRAVENOUS ANDA 1 sections
Ethacrynic acid Human Prescription Drug Label 1 72134-003 TABLET 25 mg ORAL ANDA 20 sections