Home > Compound List > Compound details
56211-40-6 molecular structure
click picture or here to close

1-({4-[(3-methylphenyl)amino]pyridin-3-yl}sulfonyl)-3-(propan-2-yl)urea

ChemBase ID: 99
Molecular Formular: C16H20N4O3S
Molecular Mass: 348.42
Monoisotopic Mass: 348.12561152
SMILES and InChIs

SMILES:
S(=O)(=O)(NC(=O)NC(C)C)c1c(Nc2cc(ccc2)C)ccnc1
Canonical SMILES:
CC(NC(=O)NS(=O)(=O)c1cnccc1Nc1cccc(c1)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

Cite this record

CBID:99 http://www.chembase.cn/molecule-99.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-({4-[(3-methylphenyl)amino]pyridin-3-yl}sulfonyl)-3-(propan-2-yl)urea
IUPAC Traditional name
torasemide
torsemide
Brand Name
Demadex
Luprac
Synonyms
Torasemida [INN-Spanish]
Torasemidum [INN-Latin]
Torsemide
Torasemide
Demadex
Torsemide
N-[[(1-Methylethyl)amino]carbonyl]-4-[(3-methylphenyl)amino]-3-pyridinesulfonamide
Torsemide
AC-4464
BM-02015
JDL-464
Luplac
Toradiur
Torem
Torasemide
Unat
CAS Number
56211-40-6
MDL Number
MFCD00866166
PubChem SID
46504760
160963562
PubChem CID
41781

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 5.9225373  H Acceptors
H Donor LogD (pH = 5.5) 1.8233185 
LogD (pH = 7.4) 1.118939  Log P 1.8639036 
Molar Refractivity 91.8931 cm3 Polarizability 35.803543 Å3
Polar Surface Area 100.19 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.76  LOG S -3.77 
Solubility (Water) 5.96e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
DMSO: soluble18 mg/mL expand Show data source
H2O: insoluble expand Show data source
Methanol expand Show data source
Water soluble expand Show data source
Apperance
solid expand Show data source
White Solid expand Show data source
Melting Point
163-164°C expand Show data source
Hydrophobicity(logP)
2.3 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
RTECS
UT7938000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
36 expand Show data source
Safety Statements
26 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H319 expand Show data source
GHS Precautionary statements
P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Purity
≥98% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C16H20N4O3S expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich DrugBank DrugBank TRC TRC Selleck Chemicals Selleck Chemicals
Sigma Aldrich - T3202 external link
Biochem/physiol Actions
Torsemide is a loop diuretic of the pyridine-sulfonylurea class with antialdosteronergic properties and inhibitor of the Na+/K+/2Cl- carrier system.
DrugBank - DB00214 external link
Item Information
Drug Groups approved
Description Torasemide (rINN) or torsemide (USAN) is a pyridine-sulfonylurea type loop diuretic mainly used in the management of edema associated with congestive heart failure. It is also used at low doses for the management of hypertension. It is marketed under the brand name Demadex. [Wikipedia]
Indication For the treatment of edema associated with congestive heart failure, renal disease, or hepatic disease. Also for the treatment of hypertension alone or in combination with other antihypertensive agents.
Pharmacology Torasemide (INN) or torsemide (USAN) is a novel loop diuretic belonging to pridine sulphonyl urea. It differs form other thiazide diuretics in that a double ring system is incorporated into its structure. Like thiazides, loop diuretics must be secreted into the tubular fluid by proximal tubule cells. In the thick ascending loop Na+ and Cl- reabsorption is accomplished by a Na+/K+/2Cl- symporter. The thick ascending limb has a high reabsorptive capacity and is responsible for reabsorbing 25% of the filtered load of Na+. The loop diuretics act by blocking this symporter. Because of the large absorptive capacity and the amount of Na+ delivered to the ascending limb, loop diuretics have a profound diuretic action. In addition, more distal nephron segments do not have the reabsorptive capacity to compensate for this increased load. The osmotic gradient for water reabsorption is also reduced resulting in an increase in the amount of water excreted.
Toxicity Symptoms of overdose include dehydration, hypovolemia, hypotension, hyponatremia, hypokalemia, hypochloremic alkalosis, and hemoconcentration. Oral LD50 in rat is 5 g/kg, and intravenous LD50 in rat is 500 mg/kg.
Affected Organisms
Humans and other mammals
Biotransformation Metabolized via the hepatic CYP2C8 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.
Absorption Rapidly absorbed following oral administration. Absolute bioavailability is 80%. Food has no effect on absorption.
Half Life 3.5 hours
Protein Binding > 99%
Elimination Torsemide is cleared from the circulation by both hepatic metabolism (approximately 80% of total clearance) and excretion into the urine (approximately 20% of total clearance in patients with normal renal function).
Distribution * 12 to 15 L [normal adults or in patients with mild to moderate renal failure or congestive heart failure]
References
Dunn CJ, Fitton A, Brogden RN: Torasemide. An update of its pharmacological properties and therapeutic efficacy. Drugs. 1995 Jan;49(1):121-42. [Pubmed]
FDA approved new drug bulletin: torsemide (Demadex), trimetrexate glucuronate (neuTrexin). RN. 1994 May;57(5):53-6. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Selleck Chemicals - S1698 external link
Research Area: Cardiovascular Disease
Biological Activity:
Torsemide(Demadex) is a pyridine-sulfonyl urea type loop diuretic with an IC50 of 2.7 ± 0.17 µM.  [1] It was mainly used in the management of edema associated with congestive heart failure. It is also used at low doses for the management of hypertension. [2]

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://en.wikipedia.org/wiki/Torasemide
  • • Dunn CJ, Fitton A, Brogden RN: Torasemide. An update of its pharmacological properties and therapeutic efficacy. Drugs. 1995 Jan;49(1):121-42. Pubmed
  • • FDA approved new drug bulletin: torsemide (Demadex), trimetrexate glucuronate (neuTrexin). RN. 1994 May;57(5):53-6. Pubmed
  • • Lesne, M., et al.: In. J. Clin. Pharmacol. Ther. Toxicol., 20, 382 (1982)
  • • Brater, D.C., et al.: Clin. Pharmacol. Ther., 42, 187 (1982)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle