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TOLAZAMIDE

CAS No.
1156-19-0
Chemical Name:
TOLAZAMIDE
Synonyms
U-17835;diabewas;tolanase;tolinase;Tolonase;norglycin;nsc-70762;olazamide;nci-c03327;TOLAZAMIDE
CBNumber:
CB9355686
Molecular Formula:
C14H21N3O3S
Molecular Weight:
311.4
MDL Number:
MFCD00083504
MOL File:
1156-19-0.mol
Last updated:2023-06-08 09:02:53

TOLAZAMIDE Properties

Melting point 162-164°C
Boiling point 300°C (rough estimate)
Density 1.2228 (rough estimate)
refractive index 1.6740 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Very slightly soluble in water; freely soluble in chloroform; soluble in acetone; slightly soluble in ethanol (96%).
form Solid
pka 3.6(at 25℃)
color White to Off-White
Water Solubility 65.4mg/L(30 ºC)
CAS DataBase Reference 1156-19-0(CAS DataBase Reference)
FDA UNII 9LT1BRO48Q
NCI Drug Dictionary Norglycin
ATC code A10BB05
EPA Substance Registry System Tolazamide (1156-19-0)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS08
Signal word  Danger
Hazard statements  H370
Precautionary statements  P260-P264-P270-P307+P311-P321-P405-P501
Hazard Codes  Xn
Risk Statements  22
Safety Statements  36
WGK Germany  3
RTECS  YT4400000
HS Code  2935904000
Toxicity LD50 in rats, mice (mg/kg): >5000 orally, 2239 i.p. (Dulin)
NFPA 704
0
1 0

TOLAZAMIDE price More Price(29)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1668001 Tolazamide United States Pharmacopeia (USP) Reference Standard 1156-19-0 200mg $436 2024-03-01 Buy
Cayman Chemical 23545 Tolazamide ≥98% 1156-19-0 5mg $68 2024-03-01 Buy
Cayman Chemical 23545 Tolazamide ≥98% 1156-19-0 10mg $121 2024-03-01 Buy
Cayman Chemical 23545 Tolazamide ≥98% 1156-19-0 25mg $268 2024-03-01 Buy
Cayman Chemical 23545 Tolazamide ≥98% 1156-19-0 50mg $469 2024-03-01 Buy
Product number Packaging Price Buy
1668001 200mg $436 Buy
23545 5mg $68 Buy
23545 10mg $121 Buy
23545 25mg $268 Buy
23545 50mg $469 Buy

TOLAZAMIDE Chemical Properties,Uses,Production

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.

Chemical Properties

White Solid

Originator

Tolinase,Upjohn,Italy,1964

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.

Uses

Labelled Tolazamide, an antidiabetic.

Definition

ChEBI: An N-sulfonylurea that is 1-tosylurea in which a hydrogen attached to the nitrogen at position 3 is replaced by an azepan-1-yl group. A hypoglycemic agent, it is used for the treatment of type 2 diabetes mellitus.

Manufacturing Process

1-Nitrosohexamethyleneimine: A solution of 89.5 grams of hexamethyleneimine, 75 ml of concentrated hydrochloric acid and 36 ml of water was heated to 70°C on a steam bath. The solution was made acidic by adding 5 ml of 2 N hydrochloric acid. While maintaining the reaction mixture at 70° to 75°C, a solution of 67 grams of sodium nitrite in 95 ml of water was added with stirring over a period of 1 hour. The mixture was then stirred at 70°C for 2 hours, and then cooled. The upper oily layer was separated and the aqueous layer was then extracted with ether. The combined ether extract and oil was dried over anhydrous magnesium sulfate and concentrated to dryness. Upon distillation of the residue there was obtained 1- nitrosohexamethyleneimine as a yellow oil, boiling at 136° to 138°C/34 mm. 1-Aminohexamethyleneimine: To a mixture of 15.18 grams of lithium aluminum hydride and 400 ml of anhydrous ether was added about 10% of a solution of 51.27 grams of 1-nitrosohexamethyleneimine in 100 ml of anhydrous ether. The mixture was refluxed until the reaction started. The remainder of the solution was added at such a rate as to maintain gentle reflux. Refluxing was continued for 2 hours more, followed by the successive addition of 16 ml of water, 12 ml of 20% aqueous sodium hydroxide solution and 56 ml of water. The inorganic precipitate was removed by filtration and washed with ether. The filtrate and ether washes were dried and the ether was removed by evaporation. Upon distillation of the residue there was obtained 25.46 grams (56%) of 1-aminohexamethyleneimine as a colorless liquid boiling at 94° to 96°C/55 mm.
N-(4-Methylbenzenesulfonyl)-N'-Hexamethyleneiminourea Free Base: A mixture of 11.42 grams of 1-aminohexamethyleneimine and 24.33 grams of 4-methylbenzenesulfonylurethane was heated at 130°C (oil-bath temperature) for 2 hours. The resulting ethanol and unreacted amine were removed at 15 mm pressure for 2 hours while keeping the oil bath at 130°C. The residue was cooled and recrystallized from methanol, giving 16.73 grams (54%) of N-(4- methylbenzenesulfonyl)-N'-hexamethyleneiminourea free base melting at 163° to 166°C. After a second recrystallization from methanol, the melting point was 163.5° to 166.5°C.

Therapeutic Function

Oral hypoglycemic

General Description

Tolazamide is N-[[(hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methylbenzenesulfonamide; or 1-(hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)urea; or 1-(4-methylphenylsulfonyl)-3-(hexahydro-1H-azepin-1-yl)urea (generic).Tolazamide incorporates a fully saturated azepine moietythat is but weakly basic, with a pKa of~3.32 The pKa of thesulfonylurea group lies within the typical range; thus, inareas of the duodenum wherein the pH falls within the rangeof 4 to 5, the uncharged form of the drug is the predominantspecies, and its lipophilicity lends to rapid absorption bypassive diffusion.

General Description

Tolazamide, 1-(hexahydro-1Hazepin-1-yl)-3-(p-tolylsulfonyl)urea (Tolinase), is an analogof tolbutamide and is reported to be effective, in general,under the same circumstances in which tolbutamide is useful.Tolazamide, however, appears to be more potent than tolbutamideand is nearly equal in potency to chlorpropamide. Instudies with radioactive tolazamide, investigators found that85% of an oral dose appeared in the urine as metabolites thatwere more soluble than tolazamide itself.

General Description

White to off-white crystalline powder. Odorless or with a slight odor.

Air & Water Reactions

TOLAZAMIDE may be sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

TOLAZAMIDE is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). TOLAZAMIDE is incompatible with acids. .

Fire Hazard

Flash point data for TOLAZAMIDE are not available; however, TOLAZAMIDE is probably combustible.

Synthesis

Tolazamide is 1-hexahydro-1H-azepin-1-yl)-3-(p-toluenesulfonyl)urea (26.2.8). By maintaining structural similarities with first-generation drugs, this drug differs from the other drugs examined in that it has a semicarbazide group instead of a urea residue, and an azepine group instead of a cyclohexyl group. It is synthesized by reacting with ethyl-(p-toluenesulfonyl)carbamate (26.2.7), which is made from p-toluenesulfonamide and ethylchloroformate, with 1-aminoazepine.

Synthesis_1156-19-0

TOLAZAMIDE Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 141)Suppliers
Supplier Tel Email Country ProdList Advantage
ATK CHEMICAL COMPANY LIMITED
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Hubei Jusheng Technology Co.,Ltd.
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Hubei xin bonus chemical co. LTD
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career henan chemical co
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TargetMol Chemicals Inc.
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Hefei TNJ Chemical Industry Co.,Ltd.
0551-65418671 sales@tnjchem.com China 34572 58
HANGZHOU CLAP TECHNOLOGY CO.,LTD
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Shaanxi Dideu Medichem Co. Ltd
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Dideu Industries Group Limited
+86-29-89586680 +86-15129568250 1026@dideu.com China 29831 58
Finetech Industry Limited
+86-27-87465837 +8618971612321 info@finetechnology-ind.com China 9589 58

View Lastest Price from TOLAZAMIDE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
TOLAZAMIDE USP/EP/BP pictures 2021-06-08 TOLAZAMIDE USP/EP/BP
1156-19-0
US $1.10 / g 1g 99.9% 100 Tons Min Dideu Industries Group Limited
TOLAZAMIDE pictures 2019-12-26 TOLAZAMIDE
1156-19-0
US $1.00 / g 1g 99% 200kg Career Henan Chemical Co
  • TOLAZAMIDE pictures
  • TOLAZAMIDE
    1156-19-0
  • US $1.00 / g
  • 99%
  • Career Henan Chemical Co
1-(hexahydro-1-azepinyl)-3-p-tolylsulfonylurea 1-(hexahydro-1h-azepin-1-yl)-3-(p-tolylsulfonyl)-ure 1-(hexahydro-1h-azepin-1-yl)-3-(p-tolylsulfonyl)urea 4-(p-tolylsulfonyl)-1,1-hexamethylenesemicarbazide Tolazamide Solution, 100ppm diabewas n-(((hexahydro-1h-azepin-1-yl)-amino)carbonyl)-4-methyl-benzenesulfonamid n-(p-toluenesulfonyl)-n’-hexamethyleniminourea n,((hexahydro-1h-azepin-1-yl)amino)carbonyl)-4-methyl-benzenesulfonamid n-[[(hexahydro-1h-azepin-1-yl)-amino]carbonyl]-4-methylbenzenesulfonamide nci-c03327 norglycin nsc-70762 tolanase tolazolamide tolinase SALOR-INT L254916-1EA N-[[(HEXAHYDRO-1H-AZEPINYL)AMINO]CARBONYL]-4-METHYLBENZENESULFONAMIDE U-17835 TOLAZAMIDE LABOTEST-BB LT00772329 1-[HEXAHYDRO-1H-AZEPIN-1-YL]-3-[P-TOLUENESULFONYL]UREA Tolonase Tolazamide (200 mg) TOLAZAMIDE;NSC 70762 1-(4-Methylphenylsulfonyl)-3-(hexahydro-1H-azepin-1-yl)urea Benzenesulfonamide, N-[[(hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methyl- Tolbutamide EP Impurity C Tolbutamide Impurity 3 (Tolbutamide EP Impurity C) TOLAZAMIDE USP/EP/BP 1-(azepan-1-yl)-3-(4-methylbenzenesulfonyl)urea 1-(azepan-1-yl)-3-(4-methylphenyl)sulfonylurea Tolazamide (1668001) BRN 2938799 BRN-2938799 4-chloro-3-[5-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-7-yl]phenol N-(Azepan-1-ylcarbamoyl)-4-methylbenzenesulfonamide 1-azepan-1-yl-3-[(4-methylphenyl)sulfonyl]urea (tolazamide) olazamide Tolbutamide Impurity C 1156-19-0 C14H21N3O3S Stimulates pancreatic islet cells to secrete insulin; blocks ATP-sensitive K+ channels. Cell Signaling and Neuroscience Cell Biology BioChemical Voltage-gated Ion Channels Potassium Channel Modulators Ion Channels Monovalent Ion Channels Amines Aromatics Intermediates & Fine Chemicals Pharmaceuticals Sulfur & Selenium Compounds TOLINASE