etacrynic acid

Small moleculeapproved

Approved

Jan 10, 1967

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. 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. Ethacrynic acid is indicated for the treatment of high blood pressure and edema caused by diseases like congestive heart failure, liver failure, and kidney failure. — NCATS

Clinical trial activity

3 trials · 3 clinical orgs · 18 marketing orgs

Phase 1
2
Phase 2
2
Phase 3
1
Phase 4
0

Earliest trial started Oct 1, 2012 (NCT01628731)

Timeline

1960s

  1. Jan 10, 1967

    Earliest FDA Approval

  2. Jan 10, 1967

    Bausch Health Companies — NDA Secondary Org

  3. Jan 10, 1967

    Bausch Health Companies — Marketing Organization

2010s

  1. Jan 1, 2012

    Earliest Phase 3 Sponsor(trial)

  2. Jan 1, 2014

    Earliest Phase 1 Sponsor(trial)

  3. Jul 29, 2015

    Bristol-Myers Squibb — Marketing Organization

  4. Jun 30, 2016

    Edenbridge Pharms — Marketing Organization

  5. Aug 23, 2016

    Mylan — Marketing Organization

  6. Feb 23, 2017

    West-Ward Pharmaceutical — Marketing Organization

  7. Feb 23, 2017

    Hikma — Marketing Organization

  8. Jul 21, 2017

    Par Pharmaceuticals — Marketing Organization

  9. Nov 17, 2017

    Zydus Discovery DMCC — Marketing Organization

  10. May 8, 2018

    Amneal Pharmaceuticals — Marketing Organization

  11. Jul 24, 2018

    Alvogen — Marketing Organization

  12. Jul 12, 2019

    Agnitio — Marketing Organization

  13. Aug 27, 2019

    Sciegen Pharmaceticals — Marketing Organization

  14. Sep 6, 2019

    Lupin — Marketing Organization

2020s

  1. Feb 19, 2020

    Upsher-Smith Laboratories — Marketing Organization

  2. Jun 9, 2020

    Vpi Pharms Inc — Marketing Organization

  3. Oct 19, 2020

    Chartwell Pharmaceuticals — Marketing Organization

  4. Oct 30, 2020

    Strides Pharma Science — Marketing Organization

Indications

Mechanism of action

Approval history

  • approvedJan 10, 1967

Chemistry & pharmacology

Loading structure…

SMILES

C=C(CC)C(=O)c1ccc(OCC(=O)O)c(Cl)c1Cl
Mol. weight
303.14 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Oral, Parenteral
Availability
Prescription Only

Oral

Yes

Parenteral

Yes

Topical

No

Sources

Also known as

  • (2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic acid
  • (2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy)acetic acid
  • acide étacrynique
  • acide étacrynique
  • ácido etacrínico
  • ácido etacrínico
  • acidum etacrynicum
  • acidum etacrynicum
  • edecrin
  • edecrin
  • edecrin
  • etacrinic acid
  • etacrinic acid
  • etacrynic acid
  • etacrynic acid
  • etacrynic acid
  • etacrynic acid
  • etacrynic acid
  • etakrinic acid
  • etakrinic acid
  • ethacryinic acid
  • ethacryinic acid
  • ethacrynate
  • ethacrynate
  • ethacrynate
  • ethacrynate
  • ethacrynate sodium
  • ethacrynate sodium
  • ethacrynate sodium
  • ethacrynate sodium
  • ethacrynic acid
  • ethacrynic acid
  • ethacrynic acid
  • ethacrynic acid
  • ethacrynic acid
  • ethacrynic acid
  • ethacrynic acid
  • hydromedin
  • hydromedin
  • methylenebutyrylphenoxyacetic acid
  • methylenebutyrylphenoxyacetic acid
  • mk-595
  • mk-595
  • reomax
  • reomax
  • sodium ethacrynate
  • sodium ethacrynate
  • sodium ethacrynate
  • sodium ethacrynate
  • sodium ethacrynate
  • sodium ethacrynate

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT02852564Phase 1Aug 1, 2016University of Kansas
NCT02051946Phase 1/Phase 2 (Phase 2)May 1, 2014Duke University
NCT01628731Phase 3Oct 1, 2012Bambino Gesù Hospital and Research Institute
Showing 3 of 3 trials
Page 1 / 1

Organizations

Research & Development (3)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Bambino Gesù Hospital and Research InstituteAcademic/Hospital1112012
Duke UniversityAcademic/Hospital1112014
University of KansasAcademic/Hospital1112016
3 organizations
Page 1 / 1

Marketing (21)

OrganizationOrg typeRelationshipDate
AgnitioFor profitMKTGJul 12, 2019
AlvogenFor profitMKTGJul 24, 2018
Amneal PharmaceuticalsFor profitMKTGMay 8, 2018
Bausch Health CompaniesFor profitNDA2Jan 10, 1967
Bausch Health CompaniesFor profitMKTGJan 10, 1967
Bristol-Myers SquibbFor profitMKTGJul 29, 2015
Chartwell PharmaceuticalsFor profitMKTGOct 19, 2020
Edenbridge PharmsFor profitMKTGJun 30, 2016
HikmaFor profitMKTGFeb 23, 2017
HikmaFor profitSYNFeb 23, 2017
LupinFor profitMKTGSep 6, 2019
MerckFor profitNDA
MylanFor profitMKTGAug 23, 2016
Par PharmaceuticalsFor profitMKTGJul 21, 2017
Par PharmaceuticalsFor profitSYNJul 29, 2015
Sciegen PharmaceticalsFor profitMKTGAug 27, 2019
Strides Pharma ScienceFor profitMKTGOct 30, 2020
Upsher-Smith LaboratoriesFor profitMKTGFeb 19, 2020
Vpi Pharms IncFor profitMKTGJun 9, 2020
West-Ward PharmaceuticalFor profitMKTGFeb 23, 2017
Zydus Discovery DMCCFor profitMKTGNov 17, 2017