TOLBUTAMIDE

Base Information

• Chemical Name: TOLBUTAMIDE
• CAS No.: 64-77-7
• Deprecated CAS: 100735-34-0
• Molecular Formula: C12H18N2O3S
• Molecular Weight: 270.353
• Hs Code.: 29350090
• European Community (EC) Number: 200-594-3
• NSC Number: 757354,23813
• UNII: 982XCM1FOI
• DSSTox Substance ID: DTXSID8021359
• Nikkaji Number: J1.406K
• Wikipedia: Tolbutamide
• Wikidata: Q414275
• NCI Thesaurus Code: C66610
• Pharos Ligand ID: TKVYUHLRN63T
• Metabolomics Workbench ID: 43349
• ChEMBL ID: CHEMBL782
• Mol file: 64-77-7.mol

Synonyms:Urea,1-butyl-3-(p-tolylsulfonyl)- (8CI);1-Butyl-3-(p-methylphenylsulfonyl)urea;1-Butyl-3-(p-tolylsulfonyl)urea;3-(p-Tolyl-4-sulfonyl)-1-butylurea;Aglicid;Arkozal;Artosin;Artozin;Butamid;Butamide;D 860;Diaben;Diabetamid;Diabetol;Diabuton;Diasulfon;Dolipol;Glyconon;HLS 831;Ipoglicone;Mobenol;N-(4-Methylbenzenesulfonyl)-N'-butylurea;N-(4-Methylphenylsulfonyl)-N'-butylurea;N-(Sulfonyl-p-methylbenzene)-N'-n-butylurea;N-(p-Methylbenzenesulfonyl)-N'-butylurea;N-(p-Tolylsulfonyl)-N'-butylcarbamide;N-Butyl-N'-(4-methylphenylsulfonyl)urea;N-Butyl-N'-(p-tolylsulfonyl)urea;N-Butyl-N'-p-toluenesulfonylurea;N-n-Butyl-N'-tosylurea;NSC 23813;NSC 87833;Orabet;Oralin;Orezan;Orinase;Orinaz;Oterben;Pramidex;Rastinon;Tolbusal;Tolbutamid;Tolbutamide;Toluina;Tolumid;Tolumide;Toluvan;U 2043;Willbutamide;

Chemical Property of TOLBUTAMIDE

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 128-130°C
• Refractive Index: 1.6360 (estimate)
• Boiling Point: white crystalline powder
• PKA: pKa 5.32(H2O t = 37) (Uncertain)
• PSA: 83.65000
• Density: 1.184 g/cm³
• LogP: 3.64560
• Storage Temp.: Refrigerator
• Solubility.: Soluble in chloroform.
• Water Solubility.: 0.14g/L(25 oC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 270.10381361
• Heavy Atom Count: 18
• Complexity: 354

Purity/Quality:

99% ^*data from raw suppliers

Tolbutamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 20/21/22-40-43-36-11
• Safety Statements: 26-36/37/39-36/37-16-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)C
• Recent ClinicalTrials: Licorice Botanical Dietary Supplements - Metabolism and Safety in Women
• Recent EU Clinical Trials: A Phase 3, 24-Week, Multi-Center, Open-Label, Randomized, Controlled Trial Comparing the Efficacy and Safety of Prandial Inhalation of Technosphere?/Insulin in Combination with Metformin or Technosphere?/Insulin Alone Versus 2 Oral Anti-Diabetic Agents (Metformin and a Secretagogue) in Subjects With Type 2 Diabetes Mellitus Sub-Optimally Controlled on Combination Metformin and a Secretagogue
• Uses: It is used for type II diabetes mellitus of medium severity with no expressed microvascular complications. Tolbutamide, have been used in a cDNA microarray assay to probe changes in gene expression in HepG2 cells upon their administration. It has been utilized to counteract insulin activity in a patch-clamp investigation of ATP sensitive K+ channels in mouse pancreatic β-cells. The activity of various biotransformation enzymes in cultured primary rat proximal tubular cells in the presence of tolbutamide and other compounds has been studied. An antidiabetic, used as a hypoglycemic agent in veterinary medicine.
• Therapeutic Function: Oral hypoglycemic
• Clinical Use: Tolbutamide should be used only when the diabetic patientis an adult or shows adult-onset diabetes, and the patientshould adhere to dietary restrictions.
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: effects enhanced by NSAIDs - avoid with azapropazone. Antibacterials: effects enhanced by chloramphenicol, sulphonamides, tetracyclines and trimethoprim; effect reduced by rifamycins. Anticoagulants: effect possibly enhanced by coumarins; also possibly changes to INR. Antifungals: concentration increased by fluconazole and miconazole, and possibly voriconazole. Lipid-regulating drugs: possibly additive hypoglycaemic effect with fibrates. Sulfinpyrazone: enhanced effect of sulphonylureas.

Technology Process of TOLBUTAMIDE

There total 17 articles about TOLBUTAMIDE 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: 97.0%

phenyl-N-butylcarbamate (3898-47-3) + toluene-4-sulfonamide (70-55-3) → N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide (64-77-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In chloroform; acetonitrile; at 80 ℃; for 8h; Flow reactor; Large scale;

DOI:10.1055/a-1664-2282

Reference yield: 95.0%

toluene-4-sulfonamide (70-55-3) + n-butyl isocyanide (111-36-4) → N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide (64-77-7)

Guidance literature:

With copper(l) chloride; In nitromethane; at 20 ℃; for 2h; Reagent/catalyst; Solvent; Catalytic behavior; Milling;

DOI:10.1039/c3cc47905f

Reference yield: 94.5%

N,N'-di-n-butylurea (1792-17-2) + sodium p-toluenesulfonamide (18522-92-4) → N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide (64-77-7) + N-butylamine (109-73-9,85404-21-3)

Guidance literature:

at 150 ℃; for 8h; Product distribution; other time;;

upstream raw materials:

N-butylcarbamoyl chloride

sodium p-toluenesulfonamide

N-(4-methylphenylsulfonyl)-N'-butylthiourea

N-butyl-O-methyl-isourea

Downstream raw materials:

N-(trifluoroacetyl)-p-toluenesulfonamide

4-hydroxytolbutamide

1-butyl-3-(p-formylphenyl)sulphonylurea

N-(tosylcarbamoyl)butyramide

Refernces

• 1、 Tanwar, Dinesh Kumar,Ratan, Anjali,Gill, Manjinder Singh. "A facile synthesis of sulfonylureas: Via water assisted preparation of carbamates". . p. 4992 - 4999. Retrieved 2017/07/11.
• 2、 Tan, Davin,?trukil, Vjekoslav,Mottillo, Cristina,Fri??i?, Tomislav. "Mechanosynthesis of pharmaceutically relevant sulfonyl-(thio)ureas". supporting information. p. 5248 - 5250. Retrieved 2014/05/06.