3-butyl-1-(4-methylbenzenesulfonyl)urea

• ChemBase ID: 995
• Molecular Formular: C12H18N2O3S
• Molecular Mass: 270.34792
• Monoisotopic Mass: 270.10381345
• SMILES: S(=O)(=O)(NC(=O)NCCCC)c1ccc(cc1)C
• Canonical SMILES: CCCCNC(=O)NS(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15)
• InChIKey: JLRGJRBPOGGCBT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-butyl-1-(4-methylbenzenesulfonyl)urea
• IUPAC Traditional name: 3-butyl-1-(4-methylbenzenesulfonyl)urea; tolbutamide
• Brand Name: Aglicid; Apo-Tolbutamide; Arkozal; Artosin; Artozin; Butamid; Butamide; Diaben; Diabetamid; Diabetol; Diabuton; Diasulfon; Dirastan; Dolipol; Drabet; Glyconon; Ipoglicone; Mobenol; Novo-Butamide; Orabet; Oralin; Orezan; Orinase; Orinase Diagnostic; Orinaz; Oterben; Pramidex; Rastinon; Restinon; Sk-tolbutamide; Tol-Tab; Tolbusal; Tolbutamid; Toluina; Tolumid; Toluvan; Tolylsulfonylbutylurea; Willbutamide
• Synonyms: Tolbutamide; 1-Butyl-3-(4-methylphenylsulfonyl)urea; N-[(Butylamino)carbonyl]-4-methyl-benzenesulfonamide; 1-Butyl-3-(p-tolylsulfonyl)urea; Tolylsulfonylbutylurea; 3-(p-Tolyl-4-sulfonyl)-1-butylurea; N-Butyl-N'-(4-methyl-phenylsulfonyl)urea; Artosin; Artozin; Mobenol; Diabetol; Orabet; Oralin; Orezan; Orinase; Orinaz; Oterben; Pramidex; Rastinon; NSC 23813; NSC 87833; 3-[p-Tolyl-4-sulfonyl]-1-butylurea; Tolbutamide; 1-n-Butyl-3-(p-tolylsulfonyl)urea; N-(Butylcarbamoyl)-4-methylbenzenesulfonamide; 1-丁基-3-(4-甲苯磺酰基)脲; 甲苯磺丁脲

Database IDs

• CAS Number: 64-77-7
• EC Number: 200-594-3
• MDL Number: MFCD00027169
• Beilstein Number: 1984428
• Merck Index: 149507
• PubChem SID: 160964458; 24870476; 46508421; 24277742
• PubChem CID: 5505

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.3339453
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.5273758
• LogD (pH = 7.4): 1.3552772
• Log P: 2.2953358
• Molar Refractivity: 70.27 cm^3
• Polarizability: 27.809378 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.04
• LOG S: -3.13
• Solubility (Water): 2.02e-01 g/l

PROPERTIES

Physical Property

• Solubility: 109 mg/L; Chloroform
• Apperance: White Solid
• Melting Point: 125-127°C; 128-130°C
• Hydrophobicity(logP): 2.2

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: YS4550000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 43
• Safety Statements: 24-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H302-H317
• GHS Precautionary statements: P261-P280-P302+P352-P321-P301+P312-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Potassium Channel
• Gene Information: human ... ALB(213), CYP1A2(1544), CYP2C9(1559), EPHX2(2053), KCNJ1(3758)mouse ... Ephx2(13850)

Product Information

• Purity: 95+%; 98%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C12H18N2O3S

DETAILS

MP Biomedicals - 02190274

Crystalline

DrugBank - DB01124

• Drug Groups: approved
• Description: Tolbutamide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It is structurally similar to acetohexamide, chlorpropamide and tolazamide and belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating β cells of the pancreas to release insulin. Sulfonylureas increase both basal insulin secretion and meal-stimulated insulin release. Medications in this class differ in their dose, rate of absorption, duration of action, route of elimination and binding site on their target pancreatic β cell receptor. Sulfonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insulin receptors. Sulfonylureas are associated with weight gain, though less so than insulin. Due to their mechanism of action, sulfonylureas may cause hypoglycemia and require consistent food intake to decrease this risk. The risk of hypoglycemia is increased in elderly, debilitated and malnourished individuals. Tolbutamide appears to be metabolized in the liver. Tolbutamide and its metabolites are excreted in urine (75-85%) and feces.
• Indication: For treatment of NIDDM (non-insulin-dependent diabetes mellitus) in conjunction with diet and exercise.
• Pharmacology: Tolbutamide, a first-generation sulfonylurea antidiabetic agent, is used with diet to lower blood glucose levels in patients with diabetes mellitus type II. Tolbutamide is twice as potent as the related second-generation agent glipizide. Tolbutamide lowers blood sugar by stimulating the pancreas to secrete insulin and helping the body use insulin efficiently. The pancreas must be able to produce insulin for this drug to work.
• Toxicity: Oral, mouse: LD₅₀ = 2600 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized in the liver principally via oxidation of the p-methyl group producing the carboxyl metabolite, 1-butyl-3-p-carboxyphenylsulfonylurea. May also be metabolized to hydroxytolbutamide. Tolbutamide does not undergo acetylation like antibacterial sulfonamides as it does not have a p-amino group.
• Absorption: Readily absorbed following oral administration. Tolbutamide is detectable in plasma 30-60 minutes following oral administration of a single dose with peak plasma concentrations occurring within 3-5 hours. ; ; Absorption is unaltered if taken with food but is increased with high pH.
• Half Life: Approximately 7 hours with interindividual variations ranging from 4-25 hours. Tolbutamide has the shortest duration of action, 6-12 hours, of the antidiabetic sulfonylureas.
• Protein Binding: Approximately 95% bound to plasma proteins.
• Elimination: Unchanged drug and metabolites are eliminated in the urine and feces. Approximately 75-85% of a single orally administered dose is excreted in the urine principally as the 1-butyl-3-p-carboxyphenylsulfonylurea within 24 hours.
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - T0891

Biochem/physiol Actions
Anti-diabetic agent. Metabolized by CYP2C9 (tolbutamide hydroxylase).

Sigma Aldrich - 46968

Biochem/physiol Actions
Anti-diabetic agent. Metabolized by CYP2C9 (tolbutamide hydroxylase).
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - T535150

An antidiabetic, used as a hypoglycemic agent in veterinary medicine.

REFERENCES

• Mourad, N., et al.: Am. J. Physiol., 299, C389 (2010)
• Van Eerdenbrugh, B., et al.: J. Pharm. Sci., 99, 3826 (2010)
• Testai, L., et al.: J. Pharm. Pharmacol., 62, 924 (2010)