3D Mol Similar

Torasemide

: 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+

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1. Names and Identifiers

: 1.1 Name; Torasemide; 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; View all

1.3 CAS No.: 56211-40-6

1.4 CID: 41781

1.5 Molecular Formula: C16H20N4O3S (isomer)

1.6 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)

1.7 InChIkey: NGBFQHCMQULJNZ-UHFFFAOYSA-N

1.8 Canonical Smiles: CC1=CC(=CC=C1)NC2=C(C=NC=C2)S(=O)(=O)NC(=O)NC(C)C

1.9 Isomers Smiles: CC1=CC(=CC=C1)NC2=C(C=NC=C2)S(=O)(=O)NC(=O)NC(C)C

2. Properties

2.1 Density: 1.283

2.1 Melting point: 163-164℃

2.1 Refractive index: 1.594

2.1 Precise Quality: 348.12600

2.1 PSA: 108.57000

2.1 logP: 4.46550

2.1 Solubility: DMSO: soluble18mg/mL

2.2 Appearance: Solid

2.3 Storage: -20°C Freezer

2.4 Chemical Properties: Crystalline Solid

2.5 Physical: Solid

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; View all

3.3 Usage: It is used as a diuretic.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36

4.1 Safety Statements: 26-37/39

4.1 Hazard Declaration: H319

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P305 + P351 + P338

4.1 WGK Germany: 2

4.1 RTECS: UT7938000

4.1 Safety: Hazard Codes:?Xi
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) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED	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. ?

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H319 Causes serious eye irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	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.
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

56211-40-6Total: 5 Synthesis Route

51498-37-4 92 Suppliers

56211-40-6 275 Suppliers

Literatures:
WO2004/9554 A1, ; Page 5-6 ;
Yield: null

72811-73-5 156 Suppliers

1795-48-8 83 Suppliers

56211-40-6 275 Suppliers

Literatures:
COSMA S.P.A. Patent: US2004/138469 A1, 2004 ; Location in patent: Page 4 ;
Yield: ~99%

17614-10-7

72811-73-5 156 Suppliers

56211-40-6 275 Suppliers

Literatures:
FINETECH LABORATORIES LTD. Patent: WO2003/97603 A1, 2003 ; Location in patent: Page/Page column 46-47 ;
Yield: ~90%

View all

8. Precursor and Product

precursor:

17614-10-7

160822-47-9

1795-48-8

33263-43-3

72811-73-5

51498-37-4

108-44-1

9. Other Information

9.0 Dissociation Constants: 7.1

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: 1-isopropyl-3-((4-(3-methylphenylamino)pyridine)-3-sulfonyl)urea

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
CACTVS Substructure Key Fingerprint: AAADceB7sABAAAAAAAAAAAAAAAAAAAAAAAA8QAAAAAAAAAABwAAAHgQQQAAADCjBWgQ/wZLIEAKoAjRnVHDCgDAxAiAI2Lw4ZJiIIGLA0dGEJAhglgLIyAcQgAAOAAAAQAAAAAAAAACAAAAAAAAAAAAAAA==

11. Question & Answer

Does Torasemide have better efficacy than furosemide in the treatment of heart failure? Feb 15 2023
AHA 2022 Annual Meeting was held in Chicago, and the TRANSFORM-HF study results were announced during the LBS.01 session. Furosemide is the most commonly used diuretic in clinical practice. However, e..
Why is Torasemide the Most Effective Diuretic for Various Conditions? Aug 08 2022
Torasemide for Injection The main site of action of loop diuretics is the thick ascending limb of the loop of Henle, where they interfere with the Na+-K+-2Cl- co-transport system, producing a powerful..
Why is Torasemide a Popular Diuretic in Clinical Practice? Mar 30 2022
In clinical practice, Torasemide is widely used due to its rapid, potent, and long-lasting diuretic effect with a low incidence of adverse reactions. It inhibits the reabsorption of sodium and chlorid..
What are the Mechanisms and Clinical Applications of Torasemide? Aug 11 2021
Torasemide is a highly efficient loop diuretic belonging to the pyridine sulfonylurea class. It is widely used in the treatment of congestive heart failure and hypertension in the field of cardiovascu..

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