Ethacrynic Acid
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Also known as Acide etacryniqueAcido etacrinicoEdecrinEtacrynic acidEthacrynateHydromedinMK-595NSC-624008NSC-85791ReomaxEtacrinic acidSID11112144SID17389016SID26746983SID855762SID92763949ethacrynic acid (EA)SID104171276SID124881979
Summary
Ethacrynic Acid (CHEMBL456) is an approved small-molecule ion transport inhibitor (ATC C03CC01); indicated across 8 conditions including cardiovascular disorder and congestive heart failure.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: C03CC01
- Indications: 8 conditions
- Clinical trials: 2
- Chemistry: 303.13 Da · C13H12Cl2O4
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL456 |
| Name | Ethacrynic Acid |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 3278 |
| ChEBI | CHEBI:4876 |
| ATC | C03CC01 |
| Molecular formula | C13H12Cl2O4 |
| Molecular weight | 303.13 |
| InChIKey | AVOLMBLBETYQHX-UHFFFAOYSA-N |
SMILES: CCC(=C)C(=O)C1=C(C(=C(C=C1)OCC(=O)O)Cl)Cl
IUPAC name: 2-[2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
ChEBI definition: An aromatic ether that is phenoxyacetic acid in which the phenyl ring is substituted by chlorines at positions 2 and 3, and by a 2-methylidenebutanoyl group at position 4. It is a loop diuretic used to treat high blood pressure resulting from diseases such as congestive heart failure, liver failure, and kidney failure. It is also a glutathione S-transferase (EC 2.5.1.18) inhibitor.
Pharmacological roles (ChEBI): ion transport inhibitor, EC 2.5.1.18 (glutathione transferase) inhibitor, loop diuretic.
Also known as: Acide etacrynique, Acido etacrinico, Edecrin, Etacrynic acid, Ethacrynate, Ethacrynic acid, Hydromedin, MK-595, NSC-624008, NSC-85791, Reomax, ethacrynic acid
Parent form; salt/anhydrous children: CHEMBL1200487
Patent coverage: 5,137 distinct patent families (20,004 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 19,987 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Broader ChEMBL bioactivity targets: 29 (assay-derived). Sample: Microtubule-associated protein tau, Nuclear receptor ROR-gamma, Fructose-bisphosphate aldolase, Prelamin-A/C, ATP-dependent DNA helicase Q1, 4’-phosphopantetheinyl transferase ffp, Thyrotropin receptor, Menin/Histone-lysine N-methyltransferase MLL, Dual specificity mitogen-activated protein kinase kinase 6, Aldo-keto reductase family 1 member B1.
Bioactivity
ChEMBL activities: 19 potent at pChembl ≥ 5 of 44 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| CYP2C9 | 6.2 | Potency | 631 | nM | CHEMBL_ACT_5061425 |
| CYP2C9 | 6.2 | AC50 | 631 | nM | CHEMBL_ACT_6019499 |
| P0DTD1 | 5.96 | IC50 | 1110 | nM | CHEMBL_ACT_25516576 |
| P07943 | 5.94 | IC50 | 1150 | nM | CHEMBL_ACT_7660864 |
| LMNA | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_3627310 |
| GSTP1 | 5.47 | IC50 | 3400 | nM | CHEMBL_ACT_2932781 |
| ABCC2 | 5.42 | IC50 | 3850 | nM | CHEMBL_ACT_18129891 |
| GSTP1 | 5.4 | IC50 | 4000 | nM | CHEMBL_ACT_1744869 |
| LMNA | 5.4 | Potency | 3981 | nM | CHEMBL_ACT_3653651 |
| PLIN1 | 5.38 | IC50 | 4190 | nM | CHEMBL_ACT_5653670 |
| MAP2K6 | 5.35 | IC50 | 4500 | nM | CHEMBL_ACT_22876492 |
| LMNA | 5.35 | Potency | 4467 | nM | CHEMBL_ACT_3645583 |
| PLIN5 | 5.32 | IC50 | 4832 | nM | CHEMBL_ACT_5564013 |
| GSTA1 | 5.3 | IC50 | 5000 | nM | CHEMBL_ACT_1744870 |
| HTT | 5.25 | Potency | 5623 | nM | CHEMBL_ACT_3762772 |
| P15917 | 5.2 | Potency | 6310 | nM | CHEMBL_ACT_4633270 |
| HSPD1 | 5.07 | IC50 | 8500 | nM | CHEMBL_ACT_19209376 |
| MAPT | 5.05 | Potency | 8912 | nM | CHEMBL_ACT_4033364 |
| MEN1 | 5.05 | Potency | 8912 | nM | CHEMBL_ACT_4562935 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
8 indications (6 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| cardiovascular disorder | 4 | MONDO:0004995 | EFO:0000319 |
| congestive heart failure | 4 | MONDO:0005009 | EFO:0000373 |
| cirrhosis of liver | 4 | MONDO:0005155 | EFO:0001422 |
| nephrotic syndrome | 4 | MONDO:0005377 | EFO:0004255 |
| urinary system disorder | 4 | MONDO:0002118 | EFO:0009690 |
| pulmonary edema | 4 | MONDO:0006932 | EFO:1001134 |
| glaucoma | 1 | MONDO:0005041 | MONDO:0005041 |
1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 2.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE3 | 1 |
| PHASE1 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT01628731 | PHASE3 | COMPLETED | Furosemide Versus Ethacrynic Acid in Children With Congenital Heart Disease |
| NCT02852564 | PHASE1 | COMPLETED | Ethacrynic Acid Elimination in Non-Muscle Invasive Bladder Cancer Patients Undergoing Transurethral Resection |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).