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ethacrynic acid 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| diuretics, etacrynic acid derivatives | 1071 | 58-54-8 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
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.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 50 | mg | O |
| 50 | mg | P |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| MRTD (Maximum Recommended Therapeutic Daily Dose) | 4.71 µM/kg/day | Contrera JF, Matthews EJ, Kruhlak NL, Benz RD |
| BA (Bioavailability) | 100 % | 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 |
| S (Water solubility) | 0.02 mg/mL | Bocci G, Oprea TI, Benet LZ |
| BDDCS (Biopharmaceutical Drug Disposition Classification System) | 4 | Bocci G, Oprea TI, Benet LZ |
Predicted pharmacokinetic/toxicological properties (PK-AZ):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| mdck-mdr1-bcrp-efflux | MDCK-MDR1-BCRP efflux ratio | 1.230 | High | 1 | |
| pfas-class | PFAS structural alert (1 = True, 0 = False) | 0 | |||
| rat-kpuu-brain | Rat brain Kpuu | 0.086 | % | High | 1 |
Approvals:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| Jan. 10, 1967 | FDA | ATON |
FDA Adverse Event Reporting System (Female)
None
FDA Adverse Event Reporting System (Male)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Drug reaction with eosinophilia and systemic symptoms | 190.85 | 53.55 | 51 | 429 | 42024 | 42578831 |
FDA Adverse Event Reporting System (Geriatric)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Drug reaction with eosinophilia and systemic symptoms | 184.50 | 31.48 | 54 | 862 | 82041 | 110506342 |
FDA Adverse Event Reporting System (Pediatric)
None
Pharmacologic Action:
| Source | Code | Description |
|---|---|---|
| ATC | C03CC01 | CARDIOVASCULAR SYSTEM DIURETICS HIGH-CEILING DIURETICS Aryloxyacetic acid derivatives |
| FDA PE | N0000175366 | Increased Diuresis at Loop of Henle |
| MeSH PA | D004232 | Diuretics |
| MeSH PA | D004791 | Enzyme Inhibitors |
| MeSH PA | D045283 | Natriuretic Agents |
| CHEBI has role | CHEBI:35554 | cardiovascular drug |
| CHEBI has role | CHEBI:35610 | antineoplastic agent |
| CHEBI has role | CHEBI:39456 | antiglaucoma drug |
| CHEBI has role | CHEBI:50184 | ion transport inhibitor |
| CHEBI has role | CHEBI:76797 | EC 2.5.1.18 (glutathione transferase) inhibitor |
| CHEBI has role | CHEBI:77608 | loop diuretic |
| CHEBI has role | CHEBI:231911 | renoprotective agent |
| CHEBI has role | CHEBI:233423 | antifibrotic agent |
| FDA EPC | N0000175590 | Loop Diuretic |
Related Drugs by ATC class:
C03CC Aryloxyacetic acid derivatives 1 drug
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| 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 |
🐶 Veterinary Drug Use
None
🐶 Veterinary products
None
Acid dissociation constants calculated using MoKa v3.0.0
| Dissociation level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 3.19 | acidic |
Orange Book patent data (new drug applications)
None
Orange Book exclusivity data (new drug applications)
None
Bioactivity Summary:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA source |
|---|---|---|---|---|---|---|---|---|---|
| Solute carrier family 12 member 1 | Transporter | INHIBITOR | WOMBAT-PK | CHEMBL | |||||
| Glutathione S-transferase P | Enzyme | IC50 | 5.47 | CHEMBL | |||||
| Glutathione S-transferase A1 | Enzyme | IC50 | 5.30 | CHEMBL | |||||
| UDP-glucose 4-epimerase | Enzyme | IC50 | 4.85 | CHEMBL | |||||
| Dual specificity mitogen-activated protein kinase kinase 6 | Kinase | IC50 | 5.35 | CHEMBL | |||||
| Glutathione S-transferase omega-1 | Enzyme | IC50 | 4.60 | CHEMBL | |||||
| 14 kDa phosphohistidine phosphatase | Enzyme | IC50 | 4.74 | CHEMBL | |||||
| Aldose reductase | Enzyme | IC50 | 5.94 | DRUG MATRIX | |||||
| Replicase polyprotein 1ab | Enzyme | IC50 | 5.96 | CHEMBL |
External reference:
| ID | Source |
|---|---|
| 4017934 | VUID |
| N0000178920 | NUI |
| D00313 | KEGG_DRUG |
| 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 |
| 6500-81-8 | SECONDARY_CAS_RN |
| M5DP350VZV | 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 |
| M5DP350VZV | INXIGHT DRUGS |
Pharmaceutical products:
| Product | Category | Ingredients | NDC | Form | Quantity | Route | Marketing | Label |
|---|---|---|---|---|---|---|---|---|
| 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 | 22 sections |
| EDECRIN | HUMAN PRESCRIPTION DRUG LABEL | 1 | 25010-215 | TABLET | 25 mg | ORAL | NDA | 22 sections |
| ETHACRYNATE 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 | 22 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 | 60760-773 | TABLET | 25 mg | ORAL | ANDA | 22 sections |
| Ethacrynic Acid | HUMAN PRESCRIPTION DRUG LABEL | 1 | 68180-159 | TABLET | 25 mg | ORAL | ANDA | 12 sections |
| Ethacrynic Acid | HUMAN PRESCRIPTION DRUG LABEL | 1 | 68180-159 | TABLET | 25 mg | ORAL | ANDA | 12 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 |
| 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 |
| ETHACRYNATE SODIUM | HUMAN PRESCRIPTION DRUG LABEL | 1 | 69315-701 | INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION | 50 mg | INTRAVENOUS | ANDA | 20 sections |
| Ethacrynic acid | Human Prescription Drug Label | 1 | 72134-003 | TABLET | 25 mg | ORAL | ANDA | 20 sections |
| Ethacrynic Acid | HUMAN PRESCRIPTION DRUG LABEL | 1 | 72162-2257 | TABLET | 25 mg | ORAL | ANDA | 21 sections |