Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H20N4O3S |
Molecular Weight | 348.42 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)NC(=O)NS(=O)(=O)C1=CN=CC=C1NC2=CC(C)=CC=C2
InChI
InChIKey=NGBFQHCMQULJNZ-UHFFFAOYSA-N
InChI=1S/C16H20N4O3S/c1-11(2)18-16(21)20-24(22,23)15-10-17-8-7-14(15)19-13-6-4-5-12(3)9-13/h4-11H,1-3H3,(H,17,19)(H2,18,20,21)
DescriptionSources: http://www.drugbank.ca/drugs/DB00214Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020136s023lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00214
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020136s023lbl.pdf
Torasemide is a pyridine-sulfonylurea type loop diuretic mainly used for the treatment of edema associated with congestive heart failure, renal disease, or hepatic disease. Also for the treatment of hypertension alone or in combination with other antihypertensive agents. It is also used at low doses for the management of hypertension. It is marketed under the brand name Demadex. Torasemide inhibits the Na+/K+/2Cl--carrier system (via interference of the chloride binding site) in the lumen of the thick ascending portion of the loop of Henle, resulting in a decrease in reabsorption of sodium and chloride. This results in an increase in the rate of delivery of tubular fluid and electrolytes to the distal sites of hydrogen and potassium ion secretion, while plasma volume contraction increases aldosterone production. The increased delivery and high aldosterone levels promote sodium reabsorption at the distal tubules, and by increasing the delivery of sodium to the distal renal tubule, torasemide indirectly increases potassium excretion via the sodium-potassium exchange mechanism. Torasemide's effects in other segments of the nephron have not been demonstrated. Thus torasemide increases the urinary excretion of sodium, chloride, and water, but it does not significantly alter glomerular filtration rate, renal plasma flow, or acid-base balance. Torasemide's effects as a antihypertensive are due to its diuretic actions. By reducing extracellular and plasma fluid volume, blood pressure is reduced temporarily, and cardiac output also decreases.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095165 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21190426 |
1.0 µM [IC50] | ||
Target ID: CHEMBL2722 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26047574 |
|||
Target ID: GO:0001998 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10406837 |
0.5 µM [IC50] | ||
Target ID: CHEMBL1874 Sources: http://www.drugbank.ca/drugs/DB00214 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Demadex Approved UseDemadex is indicated for the treatment of edema associated with congestive heart failure, renal
disease, or hepatic disease. Use of torsemide has been found to be effective for the treatment of
edema associated with chronic renal failure.
Demadex is indicated for the treatment of hypertension alone or in combination with other
antihypertensive agents. Launch Date7.4597761E11 |
|||
Primary | Demadex Approved UseDemadex is indicated for the treatment of edema associated with congestive heart failure, renal
disease, or hepatic disease. Use of torsemide has been found to be effective for the treatment of
edema associated with chronic renal failure.
Demadex is indicated for the treatment of hypertension alone or in combination with other
antihypertensive agents. Launch Date7.4597761E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
968.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19673928 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TORSEMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1549.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19673928 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
TORSEMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1561 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19673928 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TORSEMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3516 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19673928 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
TORSEMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19673928 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TORSEMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19673928 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
TORSEMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TORSEMIDE unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
400 mg 1 times / day multiple, oral Highest studied dose Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: Page: p.124 |
unhealthy Health Status: unhealthy Condition: Chronic renal failure Sources: Page: p.124 |
|
800 mg single, intravenous Highest studied dose Dose: 800 mg Route: intravenous Route: single Dose: 800 mg Sources: Page: p.124, 133 |
unhealthy Health Status: unhealthy Condition: Acute renal failure Sources: Page: p.124, 133 |
|
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Disc. AE: Dizziness, Headache... AEs leading to discontinuation/dose reduction: Dizziness (0.1 - 0.5) Sources: Page: p.11Headache (0.1 - 0.5) Nausea (0.1 - 0.5) Weakness (0.1 - 0.5) Vomiting (0.1 - 0.5) Hyperglycemia (0.1 - 0.5) Urination abnormal NOS (0.1 - 0.5) Hyperuricemia (0.1 - 0.5) Hypokalemia (0.1 - 0.5) Excessive thirst (0.1 - 0.5) Hypovolemia (0.1 - 0.5) Impotence (0.1 - 0.5) Esophageal hemorrhage (0.1 - 0.5) Dyspepsia (0.1 - 0.5) |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.6 |
Disc. AE: Electrolyte depletion, Electrolyte depletion... Other AEs: Hepatic coma, Tinnitus... AEs leading to discontinuation/dose reduction: Electrolyte depletion Other AEs:Electrolyte depletion Hypokalemia Hepatic coma Sources: Page: p.6Tinnitus Hearing loss |
200 mg 1 times / day multiple, intravenous Studied dose Dose: 200 mg, 1 times / day Route: intravenous Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy n = 44 Health Status: unhealthy Condition: Advanced chronic renal failure Population Size: 44 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dizziness | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Dyspepsia | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Esophageal hemorrhage | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Excessive thirst | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Headache | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Hyperglycemia | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Hyperuricemia | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Hypokalemia | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Hypovolemia | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Impotence | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Nausea | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Urination abnormal NOS | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Vomiting | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Weakness | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.11 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.11 |
Hearing loss | 200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.6 |
|
Hepatic coma | 200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.6 |
|
Tinnitus | 200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.6 |
|
Electrolyte depletion | Disc. AE | 200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.6 |
Electrolyte depletion | Disc. AE | 200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.6 |
Hypokalemia | Disc. AE | 200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: Page: p.6 |
unhealthy Health Status: unhealthy Condition: Edema associated with congestive heart failure, renal disease, or hepatic disease Sources: Page: p.6 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [Inhibition 100 uM] | ||||
yes [Inhibition 100 uM] | ||||
yes [Inhibition 100 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 9.0 |
minor | |||
Page: 9.0 |
minor | |||
Page: 5.0 |
yes | |||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Torasemide. A review of its pharmacological properties and therapeutic potential. | 1991 Jan |
|
Torasemide: a pharmacoeconomic review of its use in chronic heart failure. | 2001 |
|
The loop diuretic torasemide interferes with endothelin-1 actions in the aorta of hypertensive rats. | 2001 |
|
Effects of loop diuretics on angiotensin II-stimulated vascular smooth muscle cell growth. | 2001 |
|
Torasemide--a unique loop diuretic. | 2001 Apr-May |
|
[Torasemide (LUPRAC): a review of its pharmacological and clinical profile]. | 2001 Aug |
|
[Diuretics in heart failure. Can they also prolong life?]. | 2001 Dec 6 |
|
Long-term efficacy of torsemide compared with frusemide in cirrhotic patients with ascites. | 2001 Mar |
|
Optimal diuretic therapy for heart failure. | 2001 Nov |
|
[Treatment of ascites in cirrhotic patients]. | 2001 Sep |
|
Pharmacology of the thromboxane receptor antagonist and thromboxane synthase inhibitor BM-531. | 2001 Summer |
|
Torasemide in chronic heart failure: results of the TORIC study. | 2002 Aug |
|
Separation of the high-ceiling diuretic Torasemide and its metabolites by capillary zone electrophoresis with diode-array detection. | 2002 Jan |
|
Crystal forms of torasemide: new insights. | 2002 Jan |
|
[Which diuretic in heart failure? For the prognosis, they are not all equal]. | 2002 Mar 28 |
|
[Aggression to the immature kidney]. | 2002 Mar-Apr |
|
[Which loop diuretic for heart failure? For prognosis the choices are not all the same]. | 2002 Oct 3 |
|
[Torasemide (Trifas) in clinical practice--own experience]. | 2003 |
|
[Diuretics in heart failure. Fewer electrolyte disorders -- better prognosis]. | 2003 Aug 7 |
|
[Favorable prognostic effect of heart failure therapy. Diuretic makes heart muscle more elastic]. | 2003 Jun 5 |
|
Effects of the rate and composition of fluid replacement on the pharmacokinetics and pharmacodynamics of intravenous torasemide. | 2003 Nov |
|
Role of excess volume in the pathophysiology of hypertension in chronic kidney disease. | 2003 Nov |
|
Pharmacotherapy in congestive heart failure: drug absorption in the management of congestive heart failure: loop diuretics. | 2003 Sep-Oct |
|
Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro. | 2004 Dec |
|
Differential contribution of active site residues in substrate recognition sites 1 and 5 to cytochrome P450 2C8 substrate selectivity and regioselectivity. | 2004 Jun 22 |
|
A woman with infectious endocarditis caused by Abiotrophia defectiva. | 2004 Oct |
|
Pharmacological evaluation of both enantiomers of (R,S)-BM-591 as thromboxane A2 receptor antagonists and thromboxane synthase inhibitors. | 2004 Oct |
|
[Valsartan in patients with arterial hypertension and type 2 diabetes mellitus. The lapaval study]. | 2005 |
|
[The place of diuretics in the treatment of chronic heart failure. Part I]. | 2005 |
|
Functional characterization of human monocarboxylate transporter 6 (SLC16A5). | 2005 Dec |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
[Torasemide--new generation loop diuretic: clinical pharmacology and therapeutic application]. | 2006 |
|
[Diuretic therapy in heart failure]. | 2006 Jan-Feb |
|
Dose-dependent association between use of loop diuretics and mortality in advanced systolic heart failure. | 2006 Nov 15 |
|
Effects of torasemide on cardiac sympathetic nerve activity and left ventricular remodelling in patients with congestive heart failure. | 2006 Oct |
|
Torsemide renal clearance and genetic variation in luminal and basolateral organic anion transporters. | 2006 Sep |
|
Evaluation of original dual thromboxane A2 modulators as antiangiogenic agents. | 2006 Sep |
|
Hospital policies for treatment of acute decompensated heart failure. | 2007 Apr |
|
Gender difference in the pharmacokinetic interaction between oral warfarin and oxolamine in rats: inhibition of CYP2B1 by oxolamine in male rats. | 2007 Apr |
|
Genetic variation in the renal sodium transporters NKCC2, NCC, and ENaC in relation to the effects of loop diuretic drugs. | 2007 Sep |
|
Secondary pulmonary hypertension: haemodynamic effects of torasemide versus furosemide. | 2008 |
|
Comparative effects of torasemide and furosemide in rats with heart failure. | 2008 Feb 1 |
|
Torasemide, a long-acting loop diuretic, reduces the progression of myocarditis to dilated cardiomyopathy. | 2008 Feb 26 |
|
The polymorphisms Asn130Asp and Val174Ala in OATP1B1 and the CYP2C9 allele *3 independently affect torsemide pharmacokinetics and pharmacodynamics. | 2008 Jun |
Patents
Sample Use Guides
Congestive Heart Failure
The usual initial dose is 10 mg or 20 mg of once-daily oral Demadex (Torasemide). If the diuretic response is inadequate, the dose should be titrated upward by approximately doubling until the desired diuretic response is obtained. Single doses higher than 200 mg have not been adequately studied.
Chronic Renal Failure
The usual initial dose of Demadex is 20 mg of once-daily oral Demadex.
Hypertension
The usual initial dose is 5 mg once daily. If the 5 mg dose does not provide adequate reduction in blood pressure within 4 to 6 weeks, the dose may be increased to 10 mg once daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10406837
Isometric contraction induced by a submaximal concentration of Ang II (10(-7) mol/L) was reduced in a dose-dependent way by torasemide (IC(50)=0.5+/-0.04 umol/L) in cultured vascular smooth muscle cells (VSMCs) from spontaneously hypertensive rats..
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QC03CA04
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LIVERTOX |
984
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WHO-ATC |
C03CA04
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NDF-RT |
N0000175366
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NCI_THESAURUS |
C49184
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EMA VETERINARY ASSESSMENT REPORTS |
UPCARD [AUTHORIZED]
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NDF-RT |
N0000175590
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1672304
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TORASEMIDE
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C29506
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DB00214
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W31X2H97FB
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56211-40-6
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2708
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CHEMBL1148
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SUB11195MIG
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C026116
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7312
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9637
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38413
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3938
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DTXSID2023690
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41781
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M10981
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Torsemide
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W31X2H97FB
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)