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Home> Encyclopedia >Cardiovascular Agents>Pharmaceutical Intermediates>Pharmaceutical
Torasemide structure
Torasemide structure


Iupac Name:1-[4-(3-methylanilino)pyridin-3-yl]sulfonyl-3-propan-2-ylurea
CAS No.: 56211-40-6
Molecular Weight:348.421
Modify Date.: 2022-11-25 02:19
Introduction: Torasemide is a novel loop diuretic launched in 1993 after a 12-year gap from the lastdiuretic introduction. It is indicated for the treatment of hypertension and edema associatedwith chronic congestive heart failure, renal disease and hepatic cirrhosis. Torasemide exertsits major diuretic activity on the thick ascending limb of the Henle's loop to promote rapid andmarked excretion of water, Na+, Cl-, and to a lesser extent,K+ and Ca2+. Compared with otherloop diuretics such as furosemide, torasemide has a stronger antihypertensive action, ahigher bioavailability, a longer duration of action that is independent of the renal function, andhas no side effects such as paradoxical antidiuresis. The mechanism of its vasodilating effecthas been suggested to result from, at least in part, the competitive antagonism of thethromboxane A2 receptor. View more+
1. Names and Identifiers
1.1 Name
1.2 Synonyms

1-([4-[(3-Methylphenyl)amino]pyridin-3-yl]sulfonyl)-3-(propan-2-yl)urea 1-[4-(3-Methylanilino)pyridin-3-yl]sulfonyl-3-propan-2-ylurea 3-Pyridinesulfonamide, N-[[(1-methylethyl)amino]carbonyl]-4-[(3-methylphenyl)amino]- AC 4464 BM 02.015 BM 02015 DEMADEX Dilutol Examide Isemid JDL 464 JDL-464 Luprac N-(Isopropylcarbamoyl)-4-(m-tolylamino)pyridine-3-sulfonamide N-(Isopropylcarbamoyl)-4-(m-tolylamino)pyridine-3-sulfonamideTorasemide N-[(isopropylamino)carbonyl]-4-[(3-methylphenyl)amino]pyridine-3-sulfonamide N-[[(1-Methylethyl)amino]carbonyl]-4-[(3-methylphenyl)amino]-3-pyridinesulfonamide Tide 10 Toradiur Torasemide Torasemide Tables Torem Torsemide TorseMide API TorseMide(DeMadex) TroseMide Unat UpCard

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1.3 CAS No.
1.4 CID
1.5 Molecular Formula
C16H20N4O3S (isomer)
1.6 Inchi
1.7 InChIkey
1.8 Canonical Smiles
1.9 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
2.1 Refractive index
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 Solubility
DMSO: soluble18mg/mL
2.2 Appearance
2.3 Storage
-20°C Freezer
2.4 Chemical Properties
Crystalline Solid
2.5 Physical
2.6 pKa
6.44(at 25℃)
2.7 Water Solubility
Water soluble
2.8 StorageTemp
Store in original container in a cool dark place.
3. Use and Manufacturing
3.1 Definition
ChEBI: An N-sulfonylurea obtained by formal condensation of [(3-methylphenyl)amino]pyridine-3-sulfonic acid with the free amino group of N-isopropylurea.
3.2 GHS Classification
Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 71 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 2 of 71 companies. For more detailed information, please visit ECHA C&L website

Of the 7 notification(s) provided by 69 of 71 companies with hazard statement code(s):

H319 (88.41%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H361 (14.49%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P264, P280, P281, P305+P351+P338, P308+P313, P337+P313, P405, and P501
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3.3 Usage
It is used as a diuretic.
4. Safety and Handling
4.1 Hazard Codes
4.1 Risk Statements
4.1 Safety Statements
4.1 Hazard Declaration
NONH for all modes of transport
4.1 Caution Statement
P305 + P351 + P338
4.1 WGK Germany
4.1 Safety

Hazard Codes:?IrritantXi
Risk Statements: 36-36/37/38?
R36:Irritating to eyes.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S37/39:Wear suitable gloves and eye/face protection.
RTECS: UT7938000

4.2 Specification

?Torsemide (CAS NO.56211-40-6) is also named as 1-Isopropyl-3-((4-m-toluidino-3-pyridyl)sulfonyl)urea ; 3-Pyridinesulfonamide, N-(((1-methylethyl)amino)carbonyl)-4-((3-methylphenyl)amino)- ; AC 4464 ; BM 02015 ; BRN 0498515 ; CCRIS 6736 ; Demadex ; JDL 464 ; N-(((1-Methylethyl)amino)carbonyl)-4-((3-methylphenyl)amino)-3-pyridinesulfonamide ; Torasemida ; Torasemida [INN-Spanish] ; Torasemidum ; Torasemidum [INN-Latin] ; UNII-W31X2H97FB?.?Torsemide (CAS NO.56211-40-6) is crystalline solid.

4.3 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD oral > 2gm/kg (2000mg/kg) ? Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 22(Suppl,
mouse LD50 unreported > 3gm/kg (3000mg/kg) ? Annales Pharmaceutiques Francaises. Vol. 36, Pg. 369, 1978.
rat LD50 intravenous > 500mg/kg (500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)


Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 22(Suppl,
rat LD50 oral > 5gm/kg (5000mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 22(Suppl,
rat LD50 unreported > 5gm/kg (5000mg/kg) ? Annales Pharmaceutiques Francaises. Vol. 36, Pg. 369, 1978.

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2.Hazard identification

2.1 Classification of the substance or mixture

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Signal word


Hazard statement(s)

H319 Causes serious eye irritation

Precautionary statement(s)

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.


P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.





2.3 Other hazards which do not result in classification


9. Other Information
9.0 Dissociation Constants
9.1 Mesh
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. (See all compounds classified as Antihypertensive Agents.)|Agents that promote the excretion of urine through their effects on kidney function. (See all compounds classified as Diuretics.)|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. (See all compounds classified as Sodium Potassium Chloride Symporter Inhibitors.)
9.2 Absorption
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.
9.3 Metabolism
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.
9.4 Biological Half Life
The average half-life of torasemide is 3.5 hours.
9.5 Mesh Entry Terms
9.6 Use Classification
Veterinary drugs -> Isemid -> EMA Drug Category|High-ceiling diuretics, Sulfonamides, plain -> Veterinary pharmacotherapeutic group|Veterinary drugs -> UpCard -> EMA Drug Category|Sulfonamides, plain, High-ceiling diuretics -> Veterinary pharmacotherapeutic group|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals
10. Computational chemical data
  • Molecular Weight: 348.421g/mol
  • Molecular Formula: C16H20N4O3S
  • Compound Is Canonicalized: True
  • XLogP3-AA: 2.7
  • Exact Mass: 348.12561169
  • Monoisotopic Mass: 348.12561169
  • Complexity: 518
  • Rotatable Bond Count: 5
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 5
  • Topological Polar Surface Area: 109
  • Heavy Atom Count: 24
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
11. Question & Answer
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