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=CC(C)=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 Date1993 |
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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 Date1993 |
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 plasma | 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: |
unhealthy |
|
800 mg single, intravenous Highest studied dose Dose: 800 mg Route: intravenous Route: single Dose: 800 mg Sources: |
unhealthy |
|
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
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: Tinnitus Hearing loss |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Dizziness, Headache... AEs leading to discontinuation/dose reduction: Dizziness (0.1 - 0.5) Sources: Headache (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, intravenous Studied dose Dose: 200 mg, 1 times / day Route: intravenous Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hearing loss | 200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Hepatic coma | 200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Tinnitus | 200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Electrolyte depletion | Disc. AE | 200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Electrolyte depletion | Disc. AE | 200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Hypokalemia | Disc. AE | 200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Dizziness | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Dyspepsia | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Esophageal hemorrhage | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Excessive thirst | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Headache | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Hyperglycemia | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Hyperuricemia | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Hypokalemia | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Hypovolemia | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Impotence | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Nausea | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Urination abnormal NOS | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Vomiting | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Weakness | 0.1 - 0.5 Disc. AE |
200 mg 1 times / day multiple, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
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 |
|
Intraplatelet calcium levels in patients with acute renal failure before and after the administration of loop diuretics. | 2001 Mar |
|
Diuretics in the therapy of hypertension. | 2002 Mar |
|
[Which diuretic in heart failure? For the prognosis, they are not all equal]. | 2002 Mar 28 |
|
[Aggression to the immature kidney]. | 2002 Mar-Apr |
|
Torasemide vs. furosemide in primary care patients with chronic heart failure NYHA II to IV--efficacy and quality of life. | 2003 Dec |
|
[The place of diuretics in the treatment of chronic heart failure. Part I]. | 2005 |
|
Torsemide versus furosemide after continuous renal replacement therapy due to acute renal failure in cardiac surgery patients. | 2005 |
|
Screening procedure for detection of diuretics and uricosurics and/or their metabolites in human urine using gas chromatography-mass spectrometry after extractive methylation. | 2005 Aug |
|
Functional characterization of human monocarboxylate transporter 6 (SLC16A5). | 2005 Dec |
|
Dose-independent pharmacokinetics of torasemide after intravenous and oral administration to rats. | 2005 Jul |
|
Effects of enzyme inducers and inhibitors on the pharmacokinetics of intravenous torasemide in rats. | 2005 Jul 14 |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Electrochemical characterisation of the human cytochrome P450 CYP2C9. | 2005 May 15 |
|
Comparison of the urine acidification tests of torsemide vs furosemide in healthy volunteers. | 2005 Nov |
|
Pharmacological profile and therapeutic potential of BM-573, a combined thromboxane receptor antagonist and synthase inhibitor. | 2005 Spring |
|
Cardiomyopathy, familial dilated. | 2006 Jul 13 |
|
Vasodilatory action of loop diuretics: a plethysmography study of endothelial function in forearm arteries and dorsal hand veins in hypertensive patients and controls. | 2007 Feb |
|
Secondary pulmonary hypertension: haemodynamic effects of torasemide versus furosemide. | 2008 |
|
Torasemide, a long-acting loop diuretic, reduces the progression of myocarditis to dilated cardiomyopathy. | 2008 Feb 26 |
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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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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UPCARD [AUTHORIZED]
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NDF-RT |
N0000175590
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TORASEMIDE
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C29506
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DB00214
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2708
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CHEMBL1148
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Torsemide
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)