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Torasemide
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Name

Torasemide

 EINECS 637-197-3
CAS No. 56211-40-6 Density 1.283 g/cm3
PSA 108.57000 LogP 4.46550
Solubility soluble in water Melting Point 163-164 °C
Formula C16H20N4O3S Boiling Point N/A
Molecular Weight 348.426 Flash Point N/A
Transport Information N/A Appearance crystalline solid
Safety 26-37/39 Risk Codes 36-36/37/38
Molecular Structure Molecular Structure of 56211-40-6 (Torasemide) Hazard Symbols IrritantXi
Synonyms

1-[4-[(3-methylphenyl)amino]pyridin-3-yl]sulfonyl-3-propan-2-yl-urea;AC 4464;3-Pyridinesulfonamide,N-[[(1-methylethyl)- amino]carbonyl]-4-[(3-methylphenyl)amino]-;Luprac;Demadex (TN);Luprac (TN);Torasemida [INN-Spanish];Demadex;Torsemide (USP);N-(((1-Methylethyl)amino)carbonyl)-4-((3-methylphenyl)amino)-3-pyridinesulfonamide;Torsemide [USAN];JDL 464;Torasemide(3-pyridinesulfonamide,n-[[1-methylethyl)amino]carbonyl]-4-[3-methylphenyl)amino];3-Pyridinesulfonamide, N-(((1-methylethyl)amino)carbonyl)-4-((3-methylphenyl)amino)-;BM 02015;

Article Data 13

Torasemide Synthetic route

torasemide crude

torasemide crude

56211-40-6

torasemide

Conditions
ConditionsYield
In methanol; water at 75 - 80℃; for 72h; Purification / work up;100%
Stage #1: torasemide crude In methanol at 20℃; for 4h;
Stage #2: In methanol; water at 20℃; for 96h; Purification / work up;		62%
Stage #1: torasemide crude With sodium hydroxide; darco G-60 In water for 1h; Heating / reflux;
Stage #2: With acetic acid In water at 20℃; pH=7.5 - 8; Purification / work up;		61%
72811-73-5

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

1795-48-8

Isopropyl isocyanate

56211-40-6

torasemide

Conditions
ConditionsYield
Stage #1: 3-sulfonamido-4-(3'-methylphenyl) aminopyridine; Isopropyl isocyanate With potassium carbonate In diethylene glycol dimethyl ether; water at 65 - 70℃; for 0.583333h;
Stage #2: With acetic acid In diethylene glycol dimethyl ether; water at 20 - 25℃; for 3h; pH=5.3 - 5.7;		96.5%
Stage #1: 3-sulfonamido-4-(3'-methylphenyl) aminopyridine; Isopropyl isocyanate With sodium hydroxide In acetone at 20 - 30℃;
Stage #2: With acetic acid In water; acetone at 20 - 25℃; for 0.25h; pH=5.3 - 5.7;		96%
Stage #1: 3-sulfonamido-4-(3'-methylphenyl) aminopyridine; Isopropyl isocyanate With sodium hydroxide In acetone at 20 - 30℃;
Stage #2: With acetic acid In water; acetone at 20 - 25℃; for 0.25h; pH=5.5;		96%
160822-47-9

4-[(3-methylphenyl)amino]-3-pyridinesulfonamide hydrochloride

1795-48-8

Isopropyl isocyanate

56211-40-6

torasemide

Conditions
ConditionsYield
With sodium carbonate In acetone for 8 - 20h; Product distribution / selectivity; Heating / reflux;89%
With potassium carbonate In acetone for 8 - 20h; Product distribution / selectivity; Heating / reflux;88%
17614-10-7

phenyl N-isopropylcarbamate

72811-73-5

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

56211-40-6

torasemide

Conditions
ConditionsYield
Stage #1: phenyl N-isopropylcarbamate; 3-sulfonamido-4-(3'-methylphenyl) aminopyridine With triethylamine In water; acetone for 3h; Heating / reflux;
Stage #2: With sodium hydroxide In water at 20 - 25℃;
Stage #3: With sulfuric acid In water; acetone at 50 - 55℃; for 1h; Product distribution / selectivity;		87.8%
Stage #1: phenyl N-isopropylcarbamate; 3-sulfonamido-4-(3'-methylphenyl) aminopyridine With sodium hydroxide In water at 90 - 100℃; for 5h;
Stage #2: With sulfuric acid In water at 20 - 70℃; for 1h; Product distribution / selectivity;		85%
Stage #1: 3-sulfonamido-4-(3'-methylphenyl) aminopyridine With sodium hydroxide In water at 20 - 35℃;
Stage #2: phenyl N-isopropylcarbamate In water; acetone at 50 - 60℃; for 20h;
Stage #3: With sulfuric acid In water at 15 - 50℃; for 3h; pH=7.0; Product distribution / selectivity;
33263-43-3

4-chloropyridine-3-sulphonamide

108-44-1

1-amino-3-methylbenzene

1795-48-8

Isopropyl isocyanate

56211-40-6

torasemide

Conditions
ConditionsYield
copper 2.) 95 deg C, (C2H5)3N; Multistep reaction;
51498-37-4

4-hydroxypyridine-3-sulfonic acid

56211-40-6

torasemide

torsemide lithium

56211-40-6

torasemide

Conditions
ConditionsYield
With acetic acid In dimethyl sulfoxide at 20 - 30℃; for 1h;
50-00-0

formaldehyd

56211-40-6

torasemide

N-hydroxymethyltorsemide

Conditions
ConditionsYield
With sodium carbonate In ethanol at 80 - 85℃; for 2h;86%
887144-94-7

Togni's reagent II

56211-40-6

torasemide

C17H19F3N4O3S

Conditions
ConditionsYield
With sodium decatungstate; sulfuric acid; copper dichloride In water; acetonitrile at 20 - 30℃; for 12h; Irradiation; regioselective reaction;45%
67-56-1

methanol

56211-40-6

torasemide

6-(hydroxymethyl)-N-(isopropylcarbamoyl)-4-(m-tolylamino)pyridine-3-sulfonamide

Conditions
ConditionsYield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; trifluoroacetic acid; dibenzoyl peroxide for 8h; Inert atmosphere; Autoclave; Glovebox; UV-irradiation;20%

Torasemide Chemical Properties

Molecule structure of Torsemide (CAS NO.56211-40-6):

IUPAC Name: 1-[4-(3-Methylanilino)pyridin-3-yl]sulfonyl-3-propan-2-ylurea 
Molecular Weight: 348.42 g/mol
Molecular Formula: C16H20N4O3S 
Density: 1.283 g/cm3
Melting Point: 163-164 °C
Index of Refraction: 1.595
Molar Refractivity: 92.26 cm3
Molar Volume: 271.3 cm3
Surface Tension: 54.4 dyne/cm
Water Solubility: soluble
XLogP3-AA: 2.7
H-Bond Donor: 3
H-Bond Acceptor: 5
Rotatable Bond Count: 5
Tautomer Count: 6
Exact Mass: 348.125611
MonoIsotopic Mass: 348.125611
Topological Polar Surface Area: 100
Heavy Atom Count: 24
Canonical SMILES: CC1=CC(=CC=C1)NC2=C(C=NC=C2)S(=O)(=O)NC(=O)NC(C)C
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
Product Categories: Active Pharmaceutical Ingredients;Diuretic;APIs;Torasemide;All Inhibitors;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Ion transporter and other ion channel

Torasemide Uses

 Torsemide (CAS NO.56211-40-6) is used as a diuretic. It is mainly used in the management of edema associated with congestive heart failure. It is also used at low doses for the management of hypertension.

Torasemide Toxicity Data With Reference

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.
 

Torasemide Safety Profile

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

Torasemide 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.

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