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| CAS No.: | 56211-40-6 |
|---|---|
| Name: | Torasemide |
| Molecular Structure: | |
|
|
|
| Formula: | C16H20N4O3S |
| Molecular Weight: | 348.426 |
| 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; |
| EINECS: | 637-197-3 |
| Density: | 1.283 g/cm3 |
| Melting Point: | 163-164 °C |
| Solubility: | soluble in water |
| Appearance: | crystalline solid |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36-36/37/38 |
| Safety: | 26-37/39 |
| PSA: | 108.57000 |
| LogP: | 4.46550 |
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- 894852-01-87-BROMO-2,2-DIMETHYL-2H-PYRIDO[3,2-B][1,4]OXAZIN-3(4H)-ONE
- 56211-40-6
torasemide
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| copper 2.) 95 deg C, (C2H5)3N; Multistep reaction; |
- 51498-37-4
4-hydroxypyridine-3-sulfonic acid
- 56211-40-6
torasemide
- 56211-40-6
torasemide
| Conditions | Yield |
|---|---|
| With acetic acid In dimethyl sulfoxide at 20 - 30℃; for 1h; |
| Conditions | Yield |
|---|---|
| With sodium carbonate In ethanol at 80 - 85℃; for 2h; | 86% |
| Conditions | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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% |
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Chemistry
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
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.
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. |
Safety Profile
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
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.