1-(azepan-1-yl)-3-(4-methylbenzenesulfonyl)urea

• ChemBase ID: 718
• Molecular Formular: C14H21N3O3S
• Molecular Mass: 311.39984
• Monoisotopic Mass: 311.13036255
• SMILES: S(=O)(=O)(NC(=O)NN1CCCCCC1)c1ccc(cc1)C
• Canonical SMILES: O=C(NS(=O)(=O)c1ccc(cc1)C)NN1CCCCCC1
• InChI: InChI=1S/C14H21N3O3S/c1-12-6-8-13(9-7-12)21(19,20)16-14(18)15-17-10-4-2-3-5-11-17/h6-9H,2-5,10-11H2,1H3,(H2,15,16,18)
• InChIKey: OUDSBRTVNLOZBN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(azepan-1-yl)-3-(4-methylbenzenesulfonyl)urea
• IUPAC Traditional name: tolazamide; 1-(azepan-1-yl)-3-(4-methylbenzenesulfonyl)urea
• Brand Name: Norglycin; Tolanase; Tolinase
• Synonyms: 1-(Hexahydro-1H-azepin-1-yl)-3-(p-toluenesulfonyl)urea; Tolazamide; N-[[(Hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methylbenzenesulfonamide; 1-(4-Methylphenylsulfonyl)-3-(hexahydro-1H-azepin-1-yl)urea; 1-(Hexahydro-1-azepinyl)-3-p-tolylsulfonylurea; Diabewas; N-(p-Toluenesulfonyl)-N'-hexa-methyleniminourea; NSC 70762; Norglycin; Tolanase; Tolinase; U 17835; Tolazamide

Database IDs

• CAS Number: 1156-19-0
• EC Number: 214-588-3
• MDL Number: MFCD00083504
• PubChem SID: 24277741; 46505642; 160964181
• PubChem CID: 5503

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.0720177
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.0754167
• LogD (pH = 7.4): 0.9706159
• Log P: 1.91199
• Molar Refractivity: 81.3361 cm^3
• Polarizability: 32.191742 Å^3
• Polar Surface Area: 78.51 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.4
• LOG S: -3.01
• Solubility (Water): 3.08e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Solubility at pH 6.0 (mean urinary pH) is 27.8 mg/100 mL
• Apperance: White Solid
• Melting Point: 162-164°C
• Hydrophobicity(logP): 2.5

Safety Information

• Storage Condition: Refrigerator
• RTECS: YT4400000
• German water hazard class: 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: Others
• Gene Information: human ... ALB(213), KCNJ1(3758)

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB00839

• Drug Groups: approved
• Description: A sulphonylurea hypoglycemic agent with actions and uses similar to those of chlorpropamide. [PubChem]
• Indication: For use as an adjunct to diet to lower the blood glucose in patients with non-insulin dependent diabetes mellitus (Type II) whose hyperglycemia cannot be satisfactorily controlled by diet alone.
• Pharmacology: Tolazamide is an oral blood glucose lowering drug of the sulfonylurea class. Tolazamide appears to lower the blood glucose acutely by stimulating the release of insulin from the pancreas, an effect dependent upon functioning beta cells in the pancreatic islets. The mechanism by which tolazamide lowers blood glucose during long-term administration has not been clearly established. With chronic administration in Type II diabetic patients, the blood glucose lowering effect persists despite a gradual decline in the insulin secretory response to the drug. Extrapancreatic effects may be involved in the mechanism of action of oral sulfonylurea hypoglycemic drugs. Some patients who are initially responsive to oral hypoglycemic drugs, including tolazamide, may become unresponsive or poorly responsive over time. Alternatively, tolazamide may be effective in some patients who have become unresponsive to one or more other sulfonylurea drugs. In addition to its blood glucose lowering actions, tolazamide produces a mild diuresis by enhancement of renal free water clearance.
• Toxicity: Overdosage of sulfonylureas can produce hypoglycemia. Severe hypoglycemic reactions with coma, seizure, or other neurological impairment occur infrequently, but constitute medical emergencies requiring immediate hospitalization.
• Affected Organisms: Humans and other mammals
• Biotransformation: Tolazamide is metabolized to five major metabolites ranging in hypoglycemic activity from 0 to 70%.
• Absorption: Rapidly and well absorbed from the gastrointestinal tract.
• Half Life: The average biological half-life of the drug is 7 hours.
• Elimination: Tolazamide is metabolized to five major metabolites ranging in hypoglycemic activity from 0% to 70%. They are excreted principally in the urine.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - T2408

Biochem/physiol Actions
Stimulates pancreatic islet cells to secrete insulin; blocks ATP-sensitive K+ channels.

Toronto Research Chemicals - T534500

Tolazamide is an antidiabetic.

REFERENCES

• Welling, et al.: J. Pharma. Sci., 71, 1259 (1982)