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64-77-7 molecular structure
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3-butyl-1-(4-methylbenzenesulfonyl)urea

ChemBase ID: 995
Molecular Formular: C12H18N2O3S
Molecular Mass: 270.34792
Monoisotopic Mass: 270.10381345
SMILES and InChIs

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

Cite this record

CBID:995 http://www.chembase.cn/molecule-995.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.3339453  H Acceptors
H Donor LogD (pH = 5.5) 1.5273758 
LogD (pH = 7.4) 1.3552772  Log P 2.2953358 
Molar Refractivity 70.27 cm3 Polarizability 27.809378 Å3
Polar Surface Area 75.27 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.04  LOG S -3.13 
Solubility (Water) 2.02e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
109 mg/L expand Show data source
Chloroform expand Show data source
Apperance
White Solid expand Show data source
Melting Point
125-127°C expand Show data source
128-130°C expand Show data source
Hydrophobicity(logP)
2.2 expand Show data source
Storage Condition
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
YS4550000 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
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
43 expand Show data source
Safety Statements
24-37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Hazard statements
H302-H317 expand Show data source
GHS Precautionary statements
P261-P280-P302+P352-P321-P301+P312-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Target
Potassium Channel expand Show data source
Gene Information
human ... ALB(213), CYP1A2(1544), CYP2C9(1559), EPHX2(2053), KCNJ1(3758)mouse ... Ephx2(13850) expand Show data source
Purity
95+% expand Show data source
98% expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Empirical Formula (Hill Notation)
C12H18N2O3S expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB01124 external link
Item Information
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 external link
Biochem/physiol Actions
Anti-diabetic agent. Metabolized by CYP2C9 (tolbutamide hydroxylase).
Sigma Aldrich - 46968 external link
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 external link
An antidiabetic, used as a hypoglycemic agent in veterinary medicine.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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