TOLAZAMIDE

Base Information

• Chemical Name: TOLAZAMIDE
• CAS No.: 1156-19-0
• Molecular Formula: C14H21 N3 O3 S
• Molecular Weight: 311.405
• Hs Code.: 2935904000
• European Community (EC) Number: 214-588-3
• NSC Number: 758149,70762
• UNII: 9LT1BRO48Q
• DSSTox Substance ID: DTXSID3021358
• Nikkaji Number: J3.663C
• Wikipedia: Tolazamide
• Wikidata: Q7814101
• NCI Thesaurus Code: C29502
• Pharos Ligand ID: GCMLDQBHFX91
• Metabolomics Workbench ID: 43125
• ChEMBL ID: CHEMBL817
• Mol file: 1156-19-0.mol

Synonyms:Urea,1-(hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)- (6CI,7CI,8CI); 1-(4-Methylphenylsulfonyl)-3-(hexahydro-1H-azepin-1-yl)urea;1-(Hexahydro-1-azepinyl)-3-p-tolylsulfonylurea;1-(Hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)urea; Diabewas;N-(p-Toluenesulfonyl)-N'-hexamethyleniminourea; NSC 70762; Norglycin; Tolanase;Tolazamide; Tolinase; U 17835

Chemical Property of TOLAZAMIDE

Chemical Property:

• Melting Point: 162-164°C
• Refractive Index: 1.6740 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: 3.6(at 25℃)
• Flash Point: °C
• PSA: 86.89000
• Density: 1.29g/cm³
• LogP: 3.57440
• Storage Temp.: Refrigerator
• Solubility.: Very slightly soluble in water; freely soluble in chloroform; soluble in acetone; slightly soluble in ethanol (96%).
• Water Solubility.: 65.4mg/L(30 oC)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 311.13036271
• Heavy Atom Count: 21
• Complexity: 431

Purity/Quality:

99% ^*data from raw suppliers

Tolazamide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN2CCCCCC2
• Description: Tolazamide is a first generation sulfonylurea that inhibits sulfonylurea receptor 1 (SUR1) linked to the inwardly rectifying potassium channel (KIR6.2; IC50 = 4.2 μM in HEK293 cells transfected with the human receptor). It has no effect on glucose uptake in L6 rat skeletal muscle cells when used at a concentration of 0.6 mg/mL but enhances glucose uptake two-fold when used in combination with insulin. In vivo, tolazamide (128 mg/kg) reduces glomerulosclerosis and albumin excretion in a rat model of insulin-dependent diabetes induced by streptozotocin . Formulations containing tolazamide have been used in the treatment of type 2 diabetes.
• Uses: This drug is also a derivative of first generation of sulfonylurea, and it possesses stimulatory action on β-cells in pancreas, as well as the same range of action as all other drugs of the group of examined compounds. Tolazamide is used for non-insulin-dependent diabetes mellitus without expressed microvascular complications. Labelled Tolazamide, an antidiabetic. Tolazamide
• Therapeutic Function: Oral hypoglycemic

Technology Process of TOLAZAMIDE

There total 2 articles about TOLAZAMIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

Tosyl isocyanate (4083-64-1) + 1-azepanylamine (5906-35-4) → tolazamide (1156-19-0)

Guidance literature:

In dichloromethane; at 20 ℃; Inert atmosphere;

Reference yield:

→ tolazamide (1156-19-0)

Guidance literature:

Reference yield: 11.0%

tolazamide (1156-19-0) → 3,3-Hexamethylen-1-(4-tolylsulfonyl)-triazen

Guidance literature:

With potassium dihydrogenphosphate; acetic acid; sodium nitrite; In water; at 20 ℃; for 14h; Product distribution; nearly physiological in vivo conditions; other antidiabetics of the sulfonylsemicarbazide type;

DOI:10.1002/ardp.19933261203

upstream raw materials:

Tosyl isocyanate

1-azepanylamine

Refernces

• 1、 -. "Combinations comprising dipeptidylpeptidase-iv inhibitor". . . Retrieved 2008/06/13.