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Details

Stereochemistry ACHIRAL
Molecular Formula C16H19N4O3S.Na
Molecular Weight 370.4035
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TORASEMIDE SODIUM

SMILES

CC(C)[N-]C(=O)NS(=O)(=O)c1c[nH]ccc1=Nc2cccc(C)c2.[Na+]

InChI

InChIKey=BQHGMQPPSXPREC-UHFFFAOYSA-M
InChI=1S/C16H20N4O3S.Na/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,(H3,17,18,19,20,21);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula C16H20N4O3S
Molecular Weight 348.4217
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Demadex

Approved Use

Demadex 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 Date

7.4597761E11
Primary
Demadex

Approved Use

Demadex 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 Date

7.4597761E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
968.7 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
1561 ng × h/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
4.4 h
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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)
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)
Sources: Page: p.11
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
Electrolyte depletion
Hypokalemia
Other AEs:
Hepatic coma
Tinnitus
Hearing loss
Sources: Page: p.6
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

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Inhibition 100 uM]
yes [Inhibition 100 uM]
yes [Inhibition 100 uM]
Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Torasemide. A review of its pharmacological properties and therapeutic potential.
1991 Jan
Design, synthesis and biological evaluation of a sulfonylcyanoguanidine as thromboxane A2 receptor antagonist and thromboxane synthase inhibitor.
2001 May
Open-label randomized trial of torsemide compared with furosemide therapy for patients with heart failure.
2001 Nov
Torasemide in chronic heart failure: results of the TORIC study.
2002 Aug
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
Effects of acute renal failure induced by uranyl nitrate on the pharmacokinetics of intravenous torasemide in rats.
2003
[Torasemide (Trifas) in clinical practice--own experience].
2003
Ethacrynic acid and the sulfa-sensitive patient.
2003 Jan 13
The effects of the loop diuretics furosemide and torasemide on diuresis in dogs and cats.
2003 Oct
[Heart failure therapy. Cheap can become expensive].
2003 Oct 9
Calciphylaxis in chronic, non-dialysis-dependent renal disease.
2003 Sep 29
CYP2C9 polymorphisms and the interindividual variability in pharmacokinetics and pharmacodynamics of the loop diuretic drug torsemide.
2004 Dec
Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro.
2004 Dec
Pharmacological characterization of N-tert-butyl-N'-[2-(4'-methylphenylamino)-5-nitrobenzenesulfonyl]urea (BM-573), a novel thromboxane A2 receptor antagonist and thromboxane synthase inhibitor in a rat model of arterial thrombosis and its effects on bleeding time.
2004 May
A woman with infectious endocarditis caused by Abiotrophia defectiva.
2004 Oct
High-Dose Torasemide is Equivalent to High-Dose Furosemide with Hypertonic Saline in the Treatment of Refractory Congestive Heart Failure.
2005
[Valsartan in patients with arterial hypertension and type 2 diabetes mellitus. The lapaval study].
2005
Functional characterization of human monocarboxylate transporter 6 (SLC16A5).
2005 Dec
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Pharmacokinetics and pharmacodynamics of intravenous torasemide in diabetic rats induced by alloxan or streptozotocin.
2005 Nov
[Torasemide--new generation loop diuretic: clinical pharmacology and therapeutic application].
2006
[A case of severe hyponatremia in a patient suffering from epilepsy and using oxcarbazepine].
2006
[Clinical efficacy and safety of administration of loop diuretic torasemide].
2006
[Diuretic therapy in heart failure].
2006 Jan-Feb
Classification of torasemide based on the Biopharmaceutics Classification System and evaluation of the FDA biowaiver provision for generic products of CLASS I drugs.
2006 Nov
Dose-dependent association between use of loop diuretics and mortality in advanced systolic heart failure.
2006 Nov 15
[Chronotherapy with torasemide in hypertensive patients: increased efficacy and therapeutic coverage with bedtime administration].
2006 Nov 18
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
Identification of a potential cardiac antifibrotic mechanism of torasemide in patients with chronic heart failure.
2007 Aug 28
Torasemide transport by organic anion transporters contributes to hyperuricemia.
2007 Dec
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
Effect of torsemide on serum and urine electrolyte levels in dogs with congestive heart failure.
2007 Jun 16
Loop diuretics in the management of acute renal failure: a systematic review and meta-analysis.
2007 Mar
Effects of oral administration of furosemide and torsemide in healthy dogs.
2007 Oct
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
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..
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:29:30 UTC 2021
Edited
by admin
on Sat Jun 26 15:29:30 UTC 2021
Record UNII
8CJ9QM2V5Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TORASEMIDE SODIUM
WHO-DD  
Common Name English
SODIUM TORASEMIDE
Common Name English
TOREM
Brand Name English
TORASEMIDE SODIUM [WHO-DD]
Common Name English
3-PYRIDINESULFONAMIDE, N-(((1-METHYLETHYL)AMINO)CARBONYL)-4-((3-METHYLPHENYL)AMINO)-, SODIUM SALT
Systematic Name English
Code System Code Type Description
PUBCHEM
76969345
Created by admin on Sat Jun 26 15:29:30 UTC 2021 , Edited by admin on Sat Jun 26 15:29:30 UTC 2021
PRIMARY
EVMPD
SUB04922MIG
Created by admin on Sat Jun 26 15:29:30 UTC 2021 , Edited by admin on Sat Jun 26 15:29:30 UTC 2021
PRIMARY
FDA UNII
8CJ9QM2V5Q
Created by admin on Sat Jun 26 15:29:30 UTC 2021 , Edited by admin on Sat Jun 26 15:29:30 UTC 2021
PRIMARY
CAS
72810-59-4
Created by admin on Sat Jun 26 15:29:30 UTC 2021 , Edited by admin on Sat Jun 26 15:29:30 UTC 2021
NON-SPECIFIC STOICHIOMETRY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY