Product Name

  • Name

    Torasemide

  • EINECS 637-197-3
  • CAS No. 56211-40-6
  • Article Data13
  • CAS DataBase
  • Density 1.283 g/cm3
  • Solubility soluble in water
  • Melting Point 163-164 °C
  • Formula C16H20N4O3S
  • Boiling Point
  • Molecular Weight 348.426
  • Flash Point
  • Transport Information
  • 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;
  • PSA 108.57000
  • LogP 4.46550

Synthetic route

torasemide crude

torasemide crude

torasemide
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%
3-sulfonamido-4-(3'-methylphenyl) aminopyridine
72811-73-5

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

Isopropyl isocyanate
1795-48-8

Isopropyl isocyanate

torasemide
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%
4-[(3-methylphenyl)amino]-3-pyridinesulfonamide hydrochloride
160822-47-9

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

Isopropyl isocyanate
1795-48-8

Isopropyl isocyanate

torasemide
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%
phenyl N-isopropylcarbamate
17614-10-7

phenyl N-isopropylcarbamate

3-sulfonamido-4-(3'-methylphenyl) aminopyridine
72811-73-5

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

torasemide
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;
4-chloropyridine-3-sulphonamide
33263-43-3

4-chloropyridine-3-sulphonamide

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

Isopropyl isocyanate
1795-48-8

Isopropyl isocyanate

torasemide
56211-40-6

torasemide

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

4-hydroxypyridine-3-sulfonic acid

torasemide
56211-40-6

torasemide

torsemide lithium

torsemide lithium

torasemide
56211-40-6

torasemide

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

formaldehyd

torasemide
56211-40-6

torasemide

N-hydroxymethyltorsemide

N-hydroxymethyltorsemide

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

Togni's reagent II

torasemide
56211-40-6

torasemide

C17H19F3N4O3S

C17H19F3N4O3S

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

methanol

torasemide
56211-40-6

torasemide

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

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%
diazomethane
186581-53-3, 908094-01-9

diazomethane

torasemide
56211-40-6

torasemide

C17H22N4O3S
77281-96-0

C17H22N4O3S

Conditions
ConditionsYield
In diethyl ether; water; acetone
torasemide
56211-40-6

torasemide

A

4-Hydroxytorsemide

4-Hydroxytorsemide

B

3-Hydroxymethyltorsemide

3-Hydroxymethyltorsemide

C

3-Carboxy-Torasemide

3-Carboxy-Torasemide

Conditions
ConditionsYield
Rate constant; Product distribution; metabolism;
Product distribution; metabolism; pharmacokinetics and metabolism of torasemide in patients with ascites due to cirrhosis of the liver;
...Expand
torasemide
56211-40-6

torasemide

3-Carboxy-Torasemide

3-Carboxy-Torasemide

Conditions
ConditionsYield
metabolite;
torasemide
56211-40-6

torasemide

A

4-Hydroxytorsemide

4-Hydroxytorsemide

B

3-Hydroxymethyltorsemide

3-Hydroxymethyltorsemide

Conditions
ConditionsYield
With air; human liver microsomes; NADPH-generating system In phosphate buffer at 37℃; for 0.333333h; pH=7.4; Enzyme kinetics; Further Variations:; Reagents; hydroxylation;
torasemide
56211-40-6

torasemide

torsemide hydrochloride

torsemide hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water; dimethyl sulfoxide at 20℃; Product distribution / selectivity;
With hydrogenchloride In water; acetone at 20℃;
With hydrogenchloride In water; isopropyl alcohol at 20℃; Product distribution / selectivity;
torasemide
56211-40-6

torasemide

torsemide lithium

torsemide lithium

Conditions
ConditionsYield
Stage #1: torasemide With sodium hydroxide In water at 25 - 35℃;
Stage #2: With lithium hydroxide In water at 25 - 35℃; for 2h; Product distribution / selectivity;
torasemide
56211-40-6

torasemide

N-methyltorsemide phosphate

N-methyltorsemide phosphate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium carbonate / ethanol / 2 h / 80 - 85 °C
2: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 60 - 65 °C
3: sodium carbonate / acetonitrile / 8 h / 80 - 85 °C
4: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 20 °C / 15001.5 Torr / Autoclave
View Scheme
torasemide
56211-40-6

torasemide

C31H35N4O7PS

C31H35N4O7PS

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium carbonate / ethanol / 2 h / 80 - 85 °C
2: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 60 - 65 °C
3: sodium carbonate / acetonitrile / 8 h / 80 - 85 °C
View Scheme
torasemide
56211-40-6

torasemide

2Na(1+)*C17H21N4O7PS(2-)

2Na(1+)*C17H21N4O7PS(2-)

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium carbonate / ethanol / 2 h / 80 - 85 °C
2: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 60 - 65 °C
3: sodium carbonate / acetonitrile / 8 h / 80 - 85 °C
4: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 20 °C / 15001.5 Torr / Autoclave
5: sodium hydroxide / ethanol / 1 h
View Scheme
torasemide
56211-40-6

torasemide

2K(1+)*C17H21N4O7PS(2-)

2K(1+)*C17H21N4O7PS(2-)

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium carbonate / ethanol / 2 h / 80 - 85 °C
2: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 60 - 65 °C
3: sodium carbonate / acetonitrile / 8 h / 80 - 85 °C
4: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 20 °C / 15001.5 Torr / Autoclave
5: potassium hydroxide / ethanol / 1 h
View Scheme
torasemide
56211-40-6

torasemide

C17H23N4O7PS*C6H15N

C17H23N4O7PS*C6H15N

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium carbonate / ethanol / 2 h / 80 - 85 °C
2: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 60 - 65 °C
3: sodium carbonate / acetonitrile / 8 h / 80 - 85 °C
4: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 20 °C / 15001.5 Torr / Autoclave
5: ethanol / 1 h
View Scheme
torasemide
56211-40-6

torasemide

C17H23N4O7PS*C12H27N

C17H23N4O7PS*C12H27N

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium carbonate / ethanol / 2 h / 80 - 85 °C
2: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 60 - 65 °C
3: sodium carbonate / acetonitrile / 8 h / 80 - 85 °C
4: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 20 °C / 15001.5 Torr / Autoclave
5: ethanol / 1 h
View Scheme
torasemide
56211-40-6

torasemide

N-chloromethyltorsemide

N-chloromethyltorsemide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium carbonate / ethanol / 2 h / 80 - 85 °C
2: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 60 - 65 °C
View Scheme
torasemide
56211-40-6

torasemide

torsemide calcium

torsemide calcium

Conditions
ConditionsYield
With calcium hydroxide In water; isopropyl alcohol for 0.0833333h;8.3 g
torasemide
56211-40-6

torasemide

A

7-methyl-5H-pyrido[4,3-b]indole
1028067-97-1

7-methyl-5H-pyrido[4,3-b]indole

B

SK9M
1028067-98-2

SK9M

Conditions
ConditionsYield
With methanesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone at -40℃; for 24h; Scholl Reaction;

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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