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Torasemide

HCID 41781
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Basic information

CAS
56211-40-6
Standard SMILES
Cc1cccc(Nc2ccncc2S(=O)(=O)NC(=O)NC(C)C)c1
InChIKey
NGBFQHCMQULJNZ-UHFFFAOYSA-N
Molecular formula
C16H20N4O3S
Average molar mass
348.4 g/mol
Monoisotopic mass
348.12561169

Overview

Torasemide is an N-sulfonylurea obtained by formal condensation of [(3-methylphenyl)amino]pyridine-3-sulfonic acid with the free amino group of N-isopropylurea. It is a potent loop diuretic used for the treatment of hypertension and edema in patients with congestive heart failure. It has a role as an antihypertensive agent and a loop diuretic. It is an aminopyridine, a secondary amino compound and a N-sulfonylurea. It is functionally related to a 4-aminopyridine.

Names & identifiers

Preferred name
Torasemide
IUPAC
1-[[4-(3-methylanilino)-3-pyridinyl]sulfonyl]-3-propan-2-ylurea
English name
Torasemide
Molecular formula
C16H20N4O3S
Molecular weight
348.42

Names & synonyms

TorasemideTORSEMIDE56211-40-6LupracTorasemidaTorasemidumSoaanzUpcardBM-02015JDL 464AC-4464Torasemide anhydrous
Show more names
DEMADEXUnatTOREMLUPLACJDL-464GJ-1090
AC 44641-Isopropyl-3-((4-m-toluidino-3-pyridyl)sulfonyl)ureaAC4464DTXSID2023690BM 02015BM02.015N-(((1-Methylethyl)amino)carbonyl)-4-((3-methylphenyl)amino)-3-pyridinesulfonamideW31X2H97FB

Database identifiers

CAS
56211-40-6
PubChem CID
41781
DTXSID
DTXSID2023690
ChEMBL
CHEMBL1148
ChEBI
CHEBI:9637
UNII
W31X2H97FB
EC Number
637-197-3
Nikkaji
J11.135J

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
109 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
5
Heavy atoms
24
Formal charge
0
Complexity
518

Experimental & physicochemical properties

Drugs · 3 items

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

LogP · 2 items

2.3

1.21

Solubility · 3 items

Soluble

5.96e-02 g/L

>52.3 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 5 items

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Loop Diuretics

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Diuretics

Animal Drugs · 4 items

EMA approved medicines: Veterinary medicine

EMA approved medicines: Veterinary medicine

FDA approved animal drugs -> Active ingredient

Pharmaceuticals -> UK Veterinary Medicines Directorate List

Melting Point · 2 items

163-164 °C

164 - 164 °C

Physical DescriptionSolid

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 2.8% (3 of 109) of reports.

Warning

H319 (86.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P203, P264+P265, P280, P305+P351+P338, P318, P337+P317, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 109 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesEye Irrit. 2 (86.2%)

Toxicology

Adverse Effects · 1 item

* Electrolyte disturbances: As a result of diuresis, torsemide can cause electrolyte abnormalities, including hypokalemia, hypocalcemia, acid-base imbalance, etc., causing fatal cardiac arrhythmias. It is more common with IV administration and with higher doses.

Toxicity Summary · 1 item

Toxicity usually occurs with medications that can increase serum concentrations of torsemide like methotrexate, etc. No antidote is available for the treatment of toxicity. In instances of toxicity, close monitoring of kidney function and electrolytes is essential to promptly identify and treat acute kidney injury and severe electrolyte abnormalities.

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Torsemide

Ambiguous-DILI-concern

2

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Chemistry & industry

Pharmacology

ATC Code · 3 items

C03CA04

C - Cardiovascular system

QC - Cardiovascular system

Protein BindingTorasemide is found to be highly bound to plasma proteins, representing over 99% of the administered dose.
Pharmacodynamics · 1 item

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. This effect is obtained by the increase in the excretion of urinary sodium and chloride. 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. Above the aforementioned effect, torasemide presents a dual effect .in which the inhibition of aldosterone which donates torasemide with a potassium-sparing action. 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.

Mechanism of Action · 1 item

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. This action is obtained by the binding of torasemide to a chloride ion-binding site of the transport molecule. 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.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Dissociation Constants7.1

Physicochemical properties

Melting point
163 · 163-164°C
Density
1.283 · 1.283±0.06 g/cm3(Predicted)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
18 mg/mL · DMSO: soluble18mg/mL
pka
6.44 · 6.44(at 25℃)
form
solid
color
White
Water Solubility
Soluble
Merck
14 · 14,9552
BCS Class
1 · 1
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)
InChIKey
NGBFQHCMQULJNZ-UHFFFAOYSA-N
SMILES
C1=NC=CC(NC2=CC=CC(C)=C2)=C1S(NC(NC(C)C)=O)(=O)=O
CAS DataBase Reference
56211 · 56211-40-6(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
31 X2H97FB · W31X2H97FB
ATC code
3 CA04 · C03CA04
EPA Substance Registry System
3 · 3-Pyridinesulfonamide, N-[[(1-methylethyl)amino]carbonyl]-4-[(3-methylphenyl)amino]- (56211-40-6)
UNSPSC Code
41116107 · 41116107
NACRES
77 · NA.77
Protein binding
99 % · >99%
Excreted unchanged in urine
25 % · 25%
Volume of distribution
0.09 · 0.09-0.33(L/kg)
Biological half-life
3 · 3-4 / Unchanged
Symbol(GHS)
7 · GHS07,GHS08
Signal word
Warning
Hazard statements
319 · H319-H361fd
Precautionary statements
201 · P201-P202-P264-P280-P305+P351+P338-P308+P313
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi
Risk Statements
36 · 36-36/37/38
Safety Statements
26 · 26-37/39
WGK Germany
2 · 2
RTECS
7938000 · UT7938000
HS Code
2935904000 · 2935904000
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Repr · Eye Irrit. 2Repr. 2
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
rtecs
UT7938000
hs_code
2935904000
risk_code
36-36/37/38
Signal word
Warning
Symbol(GHS)
GHS07,GHS08
hazard_code
Xi
safety_code
26-37/39
Storage Class
11 - Combustible Solids
Hazard statements
H319-H361fd
Hazard Classifications
Eye Irrit. 2Repr. 2
Precautionary statements
P201-P202-P264-P280-P305+P351+P338-P308+P313
Biological Half-LifeThe average half-life of torasemide is 3.5 hours.
Metabolism/Metabolites · 2 items

Torasemide is extensively metabolized in the liver and only 20% of the dose remains unchanged and it is recovered in the urine. Metabolized via the hepatic CYP2C8 and CYP2C9 mainly by reactions of hydroxylation, oxidation and reduction to 5 metabolites. 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.

Torasemide has known human metabolites that include N-[(4-{[3-(hydroxymethyl)phenyl]imino}-1,4-dihydropyridin-3-yl)sulfonyl]propane-2-carbamimidic acid.

FDA Pharmacological Classification · 6 items

W31X2H97FB

TORSEMIDE

Physiologic Effects [PE] - Increased Diuresis at Loop of Henle

Established Pharmacologic Class [EPC] - Loop Diuretic

Torsemide is a Loop Diuretic. The physiologic effect of torsemide is by means of Increased Diuresis at Loop of Henle.

TORSEMIDE

MeSH Pharmacological Classification · 3 items

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.

Agents that promote the excretion of urine through their effects on kidney function.

Agents that inhibit SODIUM-POTASSIUM-CHLORIDE SYMPORTERS which are concentrated in the thick ascending limb at the junction of the LOOP OF HENLE and KIDNEY TUBULES, DISTAL. They act as DIURETICS. Excess use is associated with HYPOKALEMIA and HYPERGLYCEMIA.

Absorption, Distribution and Excretion · 4 items

Torasemide is the diuretic with the highest oral bioavailability even in advanced stages of chronic kidney disease. 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.

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.

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

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

Cellular LocationsCytoplasm
Metabolite PathwaysTorsemide Action Pathway

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >10000
Use ClassificationPharmaceuticals
Applications · 2 items

DescriptionTorasemide is a novel loop diuretic launched in 1993 after a 12-year gap from the last diuretic introduction. It is indicated for the treatment of hypertension and edema associated with chronic congestive heart failure, renal disease and hepatic cirrhosis. Torasemide exerts its major diuretic activity on the thick ascending limb of the Henle's loop to promote rapid and marked excretion of water, Na+, Cl-, and to a lesser extent,K+ and Ca2+. Compared with other loop diuretics such as furosemide, torasemide has a stronger antihypertensive action, a higher bioavailability, a longer duration of action that is independent of the renal function, and has no side effects such as paradoxical antidiuresis. The mechanism of its vasodilating effect has been suggested to result from, at least in part, the competitive antagonism of the thromboxane A2 receptor.

UsesTorasemide is a loop diuretic. Diuretics have been abused as performance-enhancing drugs and masking agents in doping in sports. Use of torsemide is effective for the treatment of edema associated with chronic renal failure. The pharmacology of torasemide is similar to that of frusemide,though torasemide has a longer duration of action with a plasma half-life of approximately 3.5 hours. It also causes a less marked loss of potassiumand calcium.

Upstream & downstream products

Upstream raw materials

Sodium hydroxideTriethylamine3-MethylbenzylamineAmmonium hydroxideIsopropyl isocyanate
Additional notes · 1 item

DefinitionChEBI: Torasemide is an N-sulfonylurea obtained by formal condensation of [(3-methylphenyl)amino]pyridine-3-sulfonic acid with the free amino group of N-isopropylurea. It is a potent loop diuretic used for the treatment of hypertension and edema in patients with congestive heart failure. It has a role as a loop diuretic and an antihypertensive agent. It is a N-sulfonylurea, an aminopyridine and a secondary amino compound. It is functionally related to a 4-aminopyridine.