Identification

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Name
Torasemide
Accession Number
DB00214  (APRD00295, APRD00217)
Type
Small Molecule
Groups
Approved
Description

Torasemide is a high-ceiling loop diuretic.1 Structurally, it is a pyridine-sulfnyl urea used as an antihypertensive agent.4 On the FDA records, torasemide was developed and first introduced by the company Teva Pharmaceuticals and FDA approved in 2002.9 However, torasemide was first approved for clinical use by the FDA on 1993.12

Structure
Thumb
Synonyms
  • 1-Isopropyl-3-((4-m-toluidino-3-pyridyl)sulfonyl)urea
  • N-(((1-Methylethyl)amino)carbonyl)-4-((3-methylphenyl)amino)-3-pyridinesulfonamide
  • Torasemida
  • Torasemide
  • Torasémide
  • Torasemidum
  • Torsemide
External IDs
AC-4464 / AC4464 / BM-02.015 / BM-02015 / BM02.015
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DemadexTablet5 mg/1OralMeda Pharmaceuticals Inc.2015-01-012014-12-19Us
DemadexTablet10 mg/1OralRoche Pharmaceuticals2007-02-06Not applicableUs
DemadexTablet20 mg/1OralPhysicians Total Care, Inc.2009-10-21Not applicableUs
DemadexInjection, solution10 mg/1mLIntravenousRoche Pharmaceuticals2007-02-06Not applicableUs
DemadexTablet10 mg/1OralMeda Pharmaceuticals Inc.2009-02-202009-08-04Us
DemadexTablet100 mg/1OralMEDA Pharmaceuticals2015-01-01Not applicableUs
DemadexTablet5 mg/1OralRoche Pharmaceuticals2007-02-06Not applicableUs
DemadexInjection, solution10 mg/1mLIntravenousRoche Pharmaceuticals2007-02-06Not applicableUs
DemadexTablet5 mg/1OralMeda Pharmaceuticals Inc.2009-02-202009-08-04Us
DemadexTablet20 mg/1OralMEDA Pharmaceuticals2015-01-012018-11-30Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
TorsemideTablet100 mg/1OralApotex Corporation2005-06-062018-05-11Us
TorsemideTablet100 mg/1OralCamber Pharmaceuticals, Inc.2011-01-01Not applicableUs
TorsemideTablet20 mg/1OralMed-Health Pharma, LLC.2011-07-072012-08-01Us
TorsemideTablet20 mg/1OralGreenstone, Llc2007-10-172015-06-30Us
TorsemideInjection, solution10 mg/1mLIntravenousGeneral Injectables & Vaccines2010-06-012012-06-01Us
TorsemideTablet20 mg/1OralTeva Pharmaceuticals USA, Inc.2004-06-01Not applicableUs
TorsemideTablet5 mg/1OralSun Pharmaceutical Industries Limited2008-02-262017-02-18Us
TorsemideTablet20 mg/1OralAv Pak2014-10-07Not applicableUs
TorsemideTablet10 mg/1OralTeva2010-04-192010-11-30Us
TorsemideTablet100 mg/1OralPhysicians Total Care, Inc.2012-08-17Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Britomar (Ferrer) / Diuver (Pliva) / Examide (Apex) / Luprac (Tanabe Mitshubishi Pharma) / Torem (Berlin-Chemie) / Trifas (Meranini)
Categories
UNII
W31X2H97FB
CAS number
56211-40-6
Weight
Average: 348.42
Monoisotopic: 348.125611216
Chemical Formula
C16H20N4O3S
InChI Key
NGBFQHCMQULJNZ-UHFFFAOYSA-N
InChI
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)
IUPAC Name
1-({4-[(3-methylphenyl)amino]pyridin-3-yl}sulfonyl)-3-(propan-2-yl)urea
SMILES
CC(C)NC(=O)NS(=O)(=O)C1=C(NC2=CC=CC(C)=C2)C=CN=C1

Pharmacology

Indication

Torasemide is indicated for the treatment of edema associated with congestive heart failure, renal or hepatic diseases. From this condition, it has been observed that torasemide is very effective in cases of kidney failure.Label

Edema is considered when swelling is observed due to the trap of fluid in the body tissue. It is mainly located in feet, ankles and legs but it can also be extended to other parts such as face, hands and abdomen or even the whole body.10

As well, torasemide is approved to be used as an antihypertensive agent either alone or in combination with other antihypertensives.Label

Hypertension is defined by the presence of high blood pressure. This is caused by an increase in the amount of blood pumped which in order produces the narrowing of the arteries.11

Associated Conditions
Pharmacodynamics

It is widely known that administration of torasemide can attenuate renal injury and reduce the severity of acute renal failure. This effect is obtained by increasing urine output and hence, facilitating fluid, acid-base and potassium control.2 This effect is obtained by the increase in the excretion of urinary sodium and chloride.3

Several reports have indicated that torasemide presents a long-lasting diuresis and less potassium excretion which can be explained by the effect that torasemide has on the renin-angiotensin-aldosterone system. This effect is very similar to the effect observed with the administration of combination therapy with furosemide and spironolactone and it is characterized by a decrease in plasma brain natriuretic peptide and improved measurements of left ventricular function.3

Above the aforementioned effect, torasemide presents a dual effect .in which the inhibition of aldosterone which donates torasemide with a potassium-sparing action.2

Torasemide has been shown to reduce extracellular fluid volume and blood pressure in hypertensive patients suffering from chronic kidney disease. As well, some reports have indicated that torasemide can reduce myocardial fibrosis by reducing the collagen accumulation. This effect is suggested to be related to the decrease in aldosterone which in order has been shown to reduce the production of the enzyme procollagen type I carboxy-terminal proteinase which is known to be overexpressed in heart failure patients.1

Mechanism of action

As mentioned above, torasemide is part of the loop diuretics and thus, it acts by reducing the oxygen demand in the medullary thick ascending loop of Henle by inhibiting the Na+/K+/Cl- pump on the luminal cell membrane surface.2 This action is obtained by the binding of torasemide to a chloride ion-binding site of the transport molecule.12

Torasemide is known to have an effect in the renin-angiotensin-aldosterone system by inhibiting the downstream cascade after the activation of angiotensin II. This inhibition will produce a secondary effect marked by the reduction of the expression of aldosterone synthase, TGF-B1 and thromboxane A2 and a reduction on the aldosterone receptor binding.2,3

TargetActionsOrganism
ASolute carrier family 12 member 1
inhibitor
Humans
ASolute carrier family 12 member 2
inhibitor
Humans
Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Torasemide is the diuretic with the highest oral bioavailability even in advanced stages of chronic kidney disease.1 This bioavailability tends to be higher than 80% regardless of the patient condition. The maximal serum concentration is reported to be of 1 hour and the absorption parameters are not affected by its use concomitantly with food.3

Volume of distribution

The volume of distribution of torasemide is 0.2 L/kg.5

Protein binding

Torasemide is found to be highly bound to plasma proteins, representing over 99% of the administered dose.5

Metabolism

Torasemide is extensively metabolized in the liver and only 20% of the dose remains unchanged and it is recovered in the urine.5 Metabolized via the hepatic CYP2C8 and CYP2C9 mainly by reactions of hydroxylation, oxidation and reduction to 5 metabolites.7 The major metabolite, M5, is pharmacologically inactive. There are 2 minor metabolites, M1, possessing one-tenth the activity of torasemide, and M3, equal in activity to torasemide. Overall, torasemide appears to account for 80% of the total diuretic activity, while metabolites M1 and M3 account for 9% and 11%, respectively.6

Route of elimination

Torasemide is mainly hepatically processed and excreted in the feces from which about 70-80% of the administered dose is excreted by this pathway. On the other hand, about 20-30% of the administered dose is found in the urine.12

Half life

The average half-life of torasemide is 3.5 hours.3

Clearance

The clearance rate of torasemide is considerably reduced by the presence of renal disorders.5

Toxicity

The oral LD50 of torasemide in the rat is 5 g/kg. When overdose occurs, there is a marked diuresis with the danger of loss of fluid and electrolytes which has been seen to lead to somnolence, confusion, hypotension, hyponatremia, hypokalemia, hypochloremic alkalosis, hemoconcentration dehydration and circulatory collapse. This effects can include some gastrointestinal disturbances.13

There is no increase in tumor incidence with torasemide and it is proven to not be mutagenic, not fetotoxic or teratogenic.Label

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Torsemide Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Torasemide.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Torasemide.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may decrease the antihypertensive activities of Torasemide.
1-benzylimidazole1-benzylimidazole may decrease the antihypertensive activities of Torasemide.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Torasemide.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the antihypertensive activities of Torasemide.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the antihypertensive activities of Torasemide.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the antihypertensive activities of Torasemide.
4-Methoxyamphetamine4-Methoxyamphetamine may decrease the antihypertensive activities of Torasemide.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may decrease the antihypertensive activities of Torasemide.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
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  • Action
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Food Interactions
Not Available

References

Synthesis Reference

Fritz Topfmeier, Gustav Lettenbauer, "Process for the preparation of a stable modification of torasemide." U.S. Patent USRE0345806, issued June, 1975.

USRE0345806
General References
  1. Lopez B, Gonzalez A, Hermida N, Laviades C, Diez J: Myocardial fibrosis in chronic kidney disease: potential benefits of torasemide. Kidney Int Suppl. 2008 Dec;(111):S19-23. doi: 10.1038/ki.2008.512. [PubMed:19034320]
  2. Li XM, Jin DX, Cong HL: Could torasemide be a prophylactic agent of contrast induced acute kidney injury? A review about this field. Eur Rev Med Pharmacol Sci. 2013 Jul;17(14):1845-9. [PubMed:23877845]
  3. Buggey J, Mentz RJ, Pitt B, Eisenstein EL, Anstrom KJ, Velazquez EJ, O'Connor CM: A reappraisal of loop diuretic choice in heart failure patients. Am Heart J. 2015 Mar;169(3):323-33. doi: 10.1016/j.ahj.2014.12.009. Epub 2015 Jan 6. [PubMed:25728721]
  4. Dunn CJ, Fitton A, Brogden RN: Torasemide. An update of its pharmacological properties and therapeutic efficacy. Drugs. 1995 Jan;49(1):121-42. [PubMed:7705212]
  5. Knauf H, Mutschler E: Clinical pharmacokinetics and pharmacodynamics of torasemide. Clin Pharmacokinet. 1998 Jan;34(1):1-24. doi: 10.2165/00003088-199834010-00001. [PubMed:9474471]
  6. Neugebauer G, Besenfelder E, von Mollendorff E: Pharmacokinetics and metabolism of torasemide in man. Arzneimittelforschung. 1988 Jan;38(1A):164-6. [PubMed:3370063]
  7. Barroso MB, Alonso RM, Jimenez RM: Simultaneous determination of torasemide and its major metabolite M5 in human urine by high-performance liquid chromatography-electrochemical detection. J Chromatogr Sci. 2001 Nov;39(11):491-6. [PubMed:11718311]
  8. Coleman J., Cox A. and Cowley N. (2011). Side Effects of Drugs Annual. Elsevier.
  9. FDA approvals [Link]
  10. Cleveland Clinic [Link]
  11. Hypertension Canada [Link]
  12. Indian Journal of Clinical Practice [Link]
  13. EMC [Link]
External Links
Human Metabolome Database
HMDB0014359
KEGG Drug
D00382
PubChem Compound
41781
PubChem Substance
46504760
ChemSpider
38123
BindingDB
64107
ChEBI
9637
ChEMBL
CHEMBL1148
Therapeutic Targets Database
DAP000745
PharmGKB
PA451733
RxList
RxList Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Torasemide
ATC Codes
C03CA04 — TorasemideG01AE10 — Combinations of sulfonamides
FDA label
Download (92.4 KB)
MSDS
Download (74.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableTo Determine Bioequivalence Under Fasting Conditions1
1CompletedBasic ScienceDrug Biotransformation / Membrane Transport1
1CompletedBasic ScienceGenotype-related Drug Metabolism1
1CompletedTreatmentChronic Kidney Disease (CKD) / Congestive Heart Failure (CHF)1
1CompletedTreatmentFood-Drug Interactions1
1CompletedTreatmentType 2 Diabetes Mellitus1
1Not Yet RecruitingTreatmentBody Weight Changes1
1TerminatedTreatmentHeart Failure / Impaired Renal Function1
2CompletedPreventionPreeclampsia1
2, 3CompletedTreatmentHeart Failure1
2, 3RecruitingHealth Services ResearchAcute Heart Failure (AHF)1
3RecruitingTreatmentHeart Failure1
4CompletedTreatmentCongestive Heart Failure (CHF)1
4CompletedTreatmentHigh Blood Pressure (Hypertension)2
4CompletedTreatmentRight Heart Failure / Tricuspid valve incompetence1
4RecruitingTreatmentCardiovascular Disease (CVD) / High Blood Pressure (Hypertension)1
4RecruitingTreatmentHeart Failure2
4TerminatedTreatmentCompensated Heart Failure1
4Unknown StatusTreatmentArterial Hypertension / Chronic Heart Failure (CHF)1
Not AvailableCompletedTreatmentOedema2
Not AvailableTerminatedDiagnosticAcute Decompensated Heart Failure (ADHF)1

Pharmacoeconomics

Manufacturers
  • Hoffmann la roche inc
  • Bedford laboratories
  • Luitpold pharmaceuticals inc
  • Meda pharmaceuticals inc
  • Apotex inc etobicoke site
  • Aurobindo pharma ltd
  • Hetero drugs ltd
  • Par pharmaceutical inc
  • Pliva pharmaceutical industry inc
  • Roxane laboratories inc
  • Sun pharmaceutical industries ltd
  • Teva pharmaceuticals usa inc
Packagers
  • American Regent
  • Apotex Inc.
  • Aurobindo Pharma Ltd.
  • Camber Pharmaceuticals Inc.
  • Cardinal Health
  • Diversified Healthcare Services Inc.
  • F Hoffmann-La Roche Ltd.
  • General Injectables and Vaccines Inc.
  • Greenstone LLC
  • Heartland Repack Services LLC
  • Hetero Drugs Ltd.
  • Ivax Pharmaceuticals
  • Mckesson Corp.
  • Meda AB
  • Murfreesboro Pharmaceutical Nursing Supply
  • Neuman Distributors Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Resource Optimization and Innovation LLC
  • Roxane Labs
  • Sun Pharmaceutical Industries Ltd.
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Vangard Labs Inc.
Dosage forms
FormRouteStrength
Injection, solutionIntravenous10 mg/1mL
TabletOral10 mg/1
TabletOral100 mg/1
TabletOral20 mg/1
TabletOral5 mg/1
LiquidIntravenous
TabletOral
Prices
Unit descriptionCostUnit
Demadex 100 mg tablet5.69USD tablet
Torsemide 100 mg tablet3.16USD tablet
Demadex 20 mg tablet1.59USD tablet
Demadex 10 mg tablet1.39USD tablet
Demadex 5 mg tablet1.28USD tablet
Torsemide 20 mg tablet0.85USD tablet
Torsemide 10 mg tablet0.73USD tablet
Torsemide 5 mg tablet0.66USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)163-164 °C'MSDS'
water solubilitySoluble'MSDS'
logP3.356'MSDS'
pKa7.1'FDA label'
Predicted Properties
PropertyValueSource
Water Solubility0.0596 mg/mLALOGPS
logP1.76ALOGPS
logP1.86ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)5.92ChemAxon
pKa (Strongest Basic)4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.19 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity91.89 m3·mol-1ChemAxon
Polarizability36.15 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier+0.6871
Caco-2 permeable-0.5374
P-glycoprotein substrateNon-substrate0.799
P-glycoprotein inhibitor INon-inhibitor0.7695
P-glycoprotein inhibitor IINon-inhibitor0.8232
Renal organic cation transporterNon-inhibitor0.9185
CYP450 2C9 substrateSubstrate0.6049
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7558
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.6692
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.5905
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6324
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8366
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.8740 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9854
hERG inhibition (predictor II)Non-inhibitor0.8668
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03di-0090000000-bcaf4981571fb662df86
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03di-0090000000-00cc7369c05298ea1c97
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03di-0490000000-60171fe07a2f255596e3
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-01ot-2950000000-359d6835f9bf703a0701
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000t-3910000000-a5ec65a6dbedfe7a30d3
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0564-6900000000-051171526b146f5d076c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03di-0190000000-1b2efe76058c7bf06b4a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0091000000-548edfa45514c501788d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0090000000-d7326b2b38380cd06e26
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0490000000-b9f43c4768937947d77f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0940000000-7b7084526f7c13bf6443
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00lr-0910000000-81aa8c9ff5d9a3cd3c10
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0159-0900000000-87860a9931a8414432cf
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-1590000000-1b7d966c20cec1451f6c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0490000000-bd8b6af3fe8d0f10e117
MS/MS Spectrum - , positiveLC-MS/MSsplash10-02ai-2940000000-5beb0e7e25d393903803
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0390000000-314819093d7d5a1f48f4

Taxonomy

Description
This compound belongs to the class of organic compounds known as pyridinesulfonamides. These are heterocyclic compounds containing a pyridine ring substituted by one or more sulfonamide groups.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Pyridinesulfonamides
Direct Parent
Pyridinesulfonamides
Alternative Parents
Toluenes / Sulfonylureas / Dihydropyridines / Secondary ketimines / Organosulfonic acids and derivatives / Heteroaromatic compounds / Aminosulfonyl compounds / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids and derivatives / Azacyclic compounds
show 4 more
Substituents
Pyridine-3-sulfonamide / Dihydropyridine / Toluene / Sulfonylurea / Monocyclic benzene moiety / Hydropyridine / Benzenoid / Secondary ketimine / Heteroaromatic compound / Organic sulfonic acid or derivatives
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
secondary amino compound, aminopyridine, N-sulfonylurea (CHEBI:9637)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Sodium:potassium:chloride symporter activity
Specific Function
Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume.
Gene Name
SLC12A1
Uniprot ID
Q13621
Uniprot Name
Solute carrier family 12 member 1
Molecular Weight
121449.13 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Vormfelde SV, Sehrt D, Toliat MR, Schirmer M, Meineke I, Tzvetkov M, Nurnberg P, Brockmoller J: Genetic variation in the renal sodium transporters NKCC2, NCC, and ENaC in relation to the effects of loop diuretic drugs. Clin Pharmacol Ther. 2007 Sep;82(3):300-9. Epub 2007 Apr 25. [PubMed:17460608]
  3. Fortuno A, Muniz P, Ravassa S, Rodriguez JA, Fortuno MA, Zalba G, Diez J: Torasemide inhibits angiotensin II-induced vasoconstriction and intracellular calcium increase in the aorta of spontaneously hypertensive rats. Hypertension. 1999 Jul;34(1):138-43. [PubMed:10406837]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Sodium:potassium:chloride symporter activity
Specific Function
Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume.
Gene Name
SLC12A2
Uniprot ID
P55011
Uniprot Name
Solute carrier family 12 member 2
Molecular Weight
131445.825 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Baumann P: Pharmacology and pharmacokinetics of citalopram and other SSRIs. Int Clin Psychopharmacol. 1996 Mar;11 Suppl 1:5-11. [PubMed:8732438]
  3. Hyttel J, Bogeso KP, Perregaard J, Sanchez C: The pharmacological effect of citalopram residues in the (S)-(+)-enantiomer. J Neural Transm Gen Sect. 1992;88(2):157-60. [PubMed:1632943]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Miners JO, Coulter S, Birkett DJ, Goldstein JA: Torsemide metabolism by CYP2C9 variants and other human CYP2C subfamily enzymes. Pharmacogenetics. 2000 Apr;10(3):267-70. [PubMed:10803683]
  2. Polasek TM, Elliot DJ, Lewis BC, Miners JO: Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro. J Pharmacol Exp Ther. 2004 Dec;311(3):996-1007. doi: 10.1124/jpet.104.071803. Epub 2004 Aug 10. [PubMed:15304522]
  3. Ong CE, Coulter S, Birkett DJ, Bhasker CR, Miners JO: The xenobiotic inhibitor profile of cytochrome P4502C8. Br J Clin Pharmacol. 2000 Dec;50(6):573-80. doi: 10.1046/j.1365-2125.2000.00316.x. [PubMed:11136296]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Miners JO, Coulter S, Birkett DJ, Goldstein JA: Torsemide metabolism by CYP2C9 variants and other human CYP2C subfamily enzymes. Pharmacogenetics. 2000 Apr;10(3):267-70. [PubMed:10803683]
  3. Flockhart Table of Drug Interactions [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Knauf H, Mutschler E: Clinical pharmacokinetics and pharmacodynamics of torasemide. Clin Pharmacokinet. 1998 Jan;34(1):1-24. doi: 10.2165/00003088-199834010-00001. [PubMed:9474471]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Coleman J., Cox A. and Cowley N. (2011). Side Effects of Drugs Annual. Elsevier.

Drug created on June 13, 2005 07:24 / Updated on September 02, 2019 16:38