Torsemide

Base Information

• Chemical Name: Torsemide
• CAS No.: 56211-40-6
• Molecular Formula: C16H20N4O3S
• Molecular Weight: 348.426
• Hs Code.: 2935904000
• European Community (EC) Number: 637-197-3
• UNII: W31X2H97FB
• DSSTox Substance ID: DTXSID2023690
• Nikkaji Number: J11.135J
• Wikipedia: Torasemide
• Wikidata: Q419948
• NCI Thesaurus Code: C29506
• RXCUI: 38413
• Pharos Ligand ID: DHYNXD1Z3P8J
• Metabolomics Workbench ID: 42617
• ChEMBL ID: CHEMBL1148
• Mol file: 56211-40-6.mol

Synonyms:1-isopropyl-3-((4-(3-methylphenylamino)pyridine)-3-sulfonyl)urea;1-isopropyl-3-((4-m-toluidino-3-pyridyl)sulfonyl)urea;Demadex;torasemide;torsemide

Chemical Property of Torsemide

Chemical Property:

• Appearance/Colour: crystalline solid
• Melting Point: 163-164 °C
• Refractive Index: 1.594
• PKA: 6.44(at 25℃)
• PSA: 108.57000
• Density: 1.283 g/cm³
• LogP: 4.46550
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: soluble18mg/mL
• Water Solubility.: Soluble
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 348.12561169
• Heavy Atom Count: 24
• Complexity: 518

Purity/Quality:

99.0%, ^*data from raw suppliers

Torsemide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36-36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC=C1)NC2=C(C=NC=C2)S(=O)(=O)NC(=O)NC(C)C
• Recent ClinicalTrials: Torsemide Comparison With Furosemide for Management of Patients With Stable Heart Failure
• Recent EU Clinical Trials: Pharmacogenetics of hypertension: randomized monocentric study in patients with essential hypertension and treated with Spironolactone or Torasemide
• Recent NIPH Clinical Trials: Effect of Long-Acting vs. Short-Acting Loop Diuretics and Neurohormonal Agents on Patients' Quality-of-Life Among Patients with Heart Failure
• Uses: It is used as a diuretic. Used as a diuretic. Used as a diuretic
• Description: Torasemide (Item No. 21312) is an analytical reference standard categorized as a diuretic. Diuretics, including torasemide, have been abused as performance-enhancing drugs and masking agents in doping in sports. This product is intended for research and forensic applications. Torasemide 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.
• Therapeutic Function: Diuretic
• Clinical Use: Loop diuretic: Hypertension Oedema
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: increased risk of nephrotoxicity with NSAIDs; antagonism of diuretic effect with NSAIDs. Anti-arrhythmics: risk of cardiac toxicity with anti-arrhythmics if hypokalaemia occurs; effects of lidocaine and mexiletine antagonised. Antibacterials: increased risk of ototoxicity with aminoglycosides, polymyxins and vancomycin; avoid concomitant use with lymecycline. Antidepressants: increased risk of hypokalaemia with reboxetine; enhanced hypotensive effect with MAOIs; increased risk of postural hypotension with tricyclics. Antiepileptics: increased risk of hyponatraemia with carbamazepine. Antifungals: increased risk of hypokalaemia with amphotericin. Antihypertensives: enhanced hypotensive effect; increased risk of first dose hypotensive effect with alpha-blockers; increased risk of ventricular arrhythmias with sotalol if hypokalaemia occurs. Antipsychotics: increased risk of ventricular arrhythmias with amisulpride or pimozide (avoid with pimozide) if hypokalaemia occurs; enhanced hypotensive effect with phenothiazines. Atomoxetine: hypokalaemia increases risk of ventricular arrhythmias. Cardiac glycosides: increased toxicity if hypokalaemia occurs. Cytotoxics: increased risk of ventricular arrhythmias due to hypokalaemia with arsenic trioxide; increased risk of nephrotoxicity and ototoxicity with platinum compounds. Lithium: risk of toxicity.

Technology Process of Torsemide

There total 8 articles about Torsemide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

torasemide crude → torasemide (56211-40-6)

Guidance literature:

In methanol; water; at 75 - 80 ℃; for 72h; Purification / work up;

Reference yield: 96.5%

3-sulfonamido-4-(3'-methylphenyl) aminopyridine (72811-73-5) + Isopropyl isocyanate (1795-48-8) → torasemide (56211-40-6)

Guidance literature:

3-sulfonamido-4-(3'-methylphenyl) aminopyridine; Isopropyl isocyanate; With potassium carbonate; In diethylene glycol dimethyl ether; water; at 65 - 70 ℃; for 0.583333h;

With acetic acid; In diethylene glycol dimethyl ether; water; at 20 - 25 ℃; for 3h; pH=5.3 - 5.7;

Reference yield: 89.0%

4-[(3-methylphenyl)amino]-3-pyridinesulfonamide hydrochloride (160822-47-9) + Isopropyl isocyanate (1795-48-8) → torasemide (56211-40-6)

Guidance literature:

With sodium carbonate; In acetone; for 8 - 20h; Product distribution / selectivity; Heating / reflux;

upstream raw materials:

4-chloropyridine-3-sulphonamide

1-amino-3-methylbenzene

Isopropyl isocyanate

3-sulfonamido-4-(3'-methylphenyl) aminopyridine

Downstream raw materials:

4-Hydroxytorsemide

3-Hydroxymethyltorsemide

C₁₇H₂₂N₄O₃S

Refernces

• 1、 -. "METHOD FOR THE PREPARATION OF CRYSTAL FORMS OF TORSEMIDE IN A PURE STATE". Page/Page column 7. . Retrieved 2008/06/13.
• 2、 -. "Process for the synthesis of torsemide, in particular of pure and stable form II". Page 4. . Retrieved 2008/06/13.