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Details

Stereochemistry ACHIRAL
Molecular Formula C16H20N4O3S
Molecular Weight 348.42
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TORSEMIDE

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)

HIDE SMILES / InChI

Description

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

PubMed

PubMed

TitleDatePubMed
[Treatment of ascites in cirrhotic patients].
2001 Sep
Torasemide in chronic heart failure: results of the TORIC study.
2002 Aug
[A better diuretic for patients with heart failure. Better control of potassium loss].
2002 Aug 8
[Which loop diuretic for heart failure? For prognosis the choices are not all the same].
2002 Oct 3
[Long-term diuretic treatment in heart failure: are there differences between furosemide and torasemide?].
2002 Sep 11
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
A double-blind randomized crossover trial of two loop diuretics in chronic kidney disease.
2003 Aug
[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
Multivariate optimisation of a cyclodextrin-assisted-capillary zone electrophoretic method for the separation of torasemide and its metabolites.
2003 Mar 21
Effects of torasemide on left ventricular function and neurohumoral factors in patients with chronic heart failure.
2003 May
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
The effects of the loop diuretics furosemide and torasemide on diuresis in dogs and cats.
2003 Oct
Calciphylaxis in chronic, non-dialysis-dependent renal disease.
2003 Sep 29
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
Regulatory considerations of pharmaceutical solid polymorphism in Abbreviated New Drug Applications (ANDAs).
2004 Feb 23
Optimizing bacterial expression of catalytically active human cytochromes P450: comparison of CYP2C8 and CYP2C9.
2004 Jan
Effects of loop diuretics on myocardial fibrosis and collagen type I turnover in chronic heart failure.
2004 Jun 2
[Idiopathic hypereosinophilia with cardiac involvement].
2004 Mar 12
Food: an unrecognized source of loop diuretic resistance.
2004 May
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
Pharmacological evaluation of both enantiomers of (R,S)-BM-591 as thromboxane A2 receptor antagonists and thromboxane synthase inhibitors.
2004 Oct
High-Dose Torasemide is Equivalent to High-Dose Furosemide with Hypertonic Saline in the Treatment of Refractory Congestive Heart Failure.
2005
[The place of diuretics in the treatment of chronic heart failure. Part I].
2005
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Comparison of the urine acidification tests of torsemide vs furosemide in healthy volunteers.
2005 Nov
Pharmacokinetics and pharmacodynamics of intravenous torasemide in diabetic rats induced by alloxan or streptozotocin.
2005 Nov
[Clinical efficacy and safety of administration of loop diuretic torasemide].
2006
Probable loop diuretic-induced pancreatitis in a sulfonamide-allergic patient.
2006 Jan
[Diuretic therapy in heart failure].
2006 Jan-Feb
Cardiomyopathy, familial dilated.
2006 Jul 13
Gemcitabine in combination with EGF-Receptor antibody (Cetuximab) as a treatment of cholangiocarcinoma: a case report.
2006 Jul 17
Relation of loop diuretic dose to mortality in advanced heart failure.
2006 Jun 15
Dose-dependent association between use of loop diuretics and mortality in advanced systolic heart failure.
2006 Nov 15
Evaluation of original dual thromboxane A2 modulators as antiangiogenic agents.
2006 Sep
Hospital policies for treatment of acute decompensated heart failure.
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
Genetic variation at the CYP2C locus and its association with torsemide biotransformation.
2007 Jun
Effect of torsemide on serum and urine electrolyte levels in dogs with congestive heart failure.
2007 Jun 16
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

In Vivo Use Guide
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
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..
Name Type Language
TORSEMIDE
MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
LUPRAC
Brand Name English
TORSEMIDE [MI]
Common Name English
TORSEMIDE [USAN]
Common Name English
TORSEMIDE [VANDF]
Common Name English
TORASEMIDE [JAN]
Common Name English
1-ISOPROPYL-3-((4-M-TOLUIDINO-3-PYRIDYL)SULPHONYL)UREA
Systematic Name English
TORSEMIDE [ORANGE BOOK]
Common Name English
DEMADEX
Brand Name English
TORASEMIDE [INN]
Common Name English
TORASEMIDE
INN   JAN   MART.   WHO-DD  
INN  
Official Name English
TORSEMIDE [USP-RS]
Common Name English
3-PYRIDINESULFONAMIDE, N-(((1-METHYLETHYL)AMINO)CARBONYL)-4-((3-METHYLPHENYL)AMINO)-
Systematic Name English
AC4464
Code English
AC-4464
Code English
TORASEMIDE [MART.]
Common Name English
BM02.015
Code English
BM-02015
Code English
TORASEMIDE [WHO-DD]
Common Name English
UPCARD
Brand Name English
TORASEMIDE ANHYDROUS [EMA EPAR VETERINARY]
Common Name English
BM-02.015
Code English
TORSEMIDE [USP]
Common Name English
TORASEMIDE ANHYDROUS
Common Name English
Classification Tree Code System Code
WHO-VATC QC03CA04
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
LIVERTOX 984
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
WHO-ATC C03CA04
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
NDF-RT N0000175366
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
NCI_THESAURUS C49184
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
EMA VETERINARY ASSESSMENT REPORTS UPCARD [AUTHORIZED]
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
NDF-RT N0000175590
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
Code System Code Type Description
WIKIPEDIA
TORASEMIDE
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
PRIMARY
LactMed
56211-40-6
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
PRIMARY
NCI_THESAURUS
C29506
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
PRIMARY
DRUG BANK
DB00214
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
PRIMARY
CAS
56211-40-6
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
PRIMARY
ChEMBL
CHEMBL1148
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
PRIMARY
EVMPD
SUB11195MIG
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
PRIMARY
MESH
C026116
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
PRIMARY
IUPHAR
7312
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
PRIMARY
RXCUI
38413
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
PRIMARY RxNorm
INN
3938
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
PRIMARY
EPA CompTox
56211-40-6
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
PRIMARY
PUBCHEM
41781
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
PRIMARY
MERCK INDEX
M10981
Created by admin on Mon Oct 21 19:54:14 UTC 2019 , Edited by admin on Mon Oct 21 19:54:14 UTC 2019
PRIMARY Merck Index