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TOLBUTAMIDE

CAS No.
64-77-7
Chemical Name:
TOLBUTAMIDE
Synonyms
Diaben;ORINASE;IRKG;d860;u2043;IRK16;GIRK4;BZ 55;D 860;tolbet
CBNumber:
CB4709039
Molecular Formula:
C12H18N2O3S
Molecular Weight:
270.35
MDL Number:
MFCD00027169
MOL File:
64-77-7.mol
MSDS File:
SDS
Last updated:2023-05-18 11:31:14

TOLBUTAMIDE Properties

Melting point 128-130°C
Density 1.2450
refractive index 1.6360 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Soluble in chloroform.
pka pKa 5.32(H2O t = 37) (Uncertain)
color White to Off-White
Water Solubility 0.14g/L(25 ºC)
Merck 14,9507
BRN 1984428
Specific Activity 50-60 mCi/mmol
Concentration 0.1 mCi/ml
Solvent Ethanol
Stability Stable. Combustible.
CAS DataBase Reference 64-77-7(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 982XCM1FOI
ATC code A10BB03,V04CA01
NCI Drug Dictionary tolbutamide
EPA Substance Registry System Tolbutamide (64-77-7)

Pharmacokinetic data

Protein binding 95-97%
Volume of distribution 0.1-0.15(L/kg)
Biological half-life 4-7 / Unchanged

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H317
Precautionary statements  P261-P280g-P301+P312a-P321-P333+P313-P501a
Hazard Codes  F,Xn
Risk Statements  20/21/22-40-43-36-11
Safety Statements  26-36/37/39-36/37-16-24/25
WGK Germany  2
RTECS  YS4550000
TSCA  Yes
HS Code  29350090
Toxicity LD50 oral in rat: 2490mg/kg
NFPA 704
1
2 0

TOLBUTAMIDE price More Price(28)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR3251 Tolbutamide pharmaceutical secondary standard, certified reference material 64-77-7 500MG $173 2024-03-01 Buy
Sigma-Aldrich 1670003 Tolbutamide United States Pharmacopeia (USP) Reference Standard 64-77-7 200mg $412 2024-03-01 Buy
Sigma-Aldrich 46968 Tolbutamide VETRANAL?, analytical standard 64-77-7 250mg $53.6 2022-05-15 Buy
TCI Chemical T3690 Tolbutamide >98.0%(HPLC)(T) 64-77-7 1g $26 2024-03-01 Buy
Alfa Aesar B21698 Tolbutamide, 98% 64-77-7 10g $48.65 2024-03-01 Buy
Product number Packaging Price Buy
PHR3251 500MG $173 Buy
1670003 200mg $412 Buy
46968 250mg $53.6 Buy
T3690 1g $26 Buy
B21698 10g $48.65 Buy

TOLBUTAMIDE Chemical Properties,Uses,Production

Chemical Properties

White or almost white, crystalline powder.

Originator

Dolipol,Hoechst,France,1956

Uses

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

Uses

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.

Uses

It is used for type II diabetes mellitus of medium severity with no expressed microvascular complications.

Definition

ChEBI: An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.

Manufacturing Process

50 grams of n-butyl isocyanate are stirred at room temperature into a suspension of 96 grams of sodium 4-methyl-benzenesulfonamide in 120 cc of dry nitrobenzene and the whole is then heated for 7 hours at 100°C. After being cooled, the reaction mixture, which is a thick magma, is diluted with methylene chloride or ethyl acetate and the sodium salt of the sulfonylurea formed is separated by centrifuging. The centrifuged crystalline residue freed from organic solvents is dissolved in 500 to 600 cc of water heated at 50°C and decolorized with animal charcoal.
The precipitate obtained by acidification with dilute hydrochloric acid is dissolved in an equivalent quantity of dilute ammonia solution (about 1:20), again treated with animal charcoal and reprecipitated with dilute hydrochloric acid. In this manner N-4-methylbenzenesulfonyl-N'-n-butyl-urea is obtained in analytically pure form in a yield of 70 to 80% of theory. It melts at 125° to 127°C (with decomposition).

Therapeutic Function

Oral hypoglycemic

General Description

White crystals.

General Description

Tolbutamide, 1-butyl-3-(p-tolylsulfonyl)urea (Orinase), occurs as a white, crystalline powderthat is insoluble in water and soluble in alcohol or aqueousalkali. It is stable in air.
Tolbutamide is absorbed rapidly in responsive diabetic patients.The blood sugar level reaches a minimum after 5 to8 hours. It is oxidized rapidly in vivo to 1-butyl-3-(p-carboxyphenyl)sulfonylurea, which is inactive. The metabolite isfreely soluble at urinary pH; if the urine is strongly acidified,however, as in the use of sulfosalicylic acid as a protein precipitant,a white precipitate of the free acid may be formed.

General Description

Tolbutamide is N-[(butylamino)carbonyl]-4-methylbenzenesulfonamide;or 1-butyl-3-(p-tolylsulfonyl)urea (Orinase,generic). Orinase Diagnostic was the sodium salt, which isfreely soluble in water for injection, but this product was discontinuedc. 2000.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

TOLBUTAMIDE 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). TOLBUTAMIDE is incompatible with acids. .

Fire Hazard

Flash point data for TOLBUTAMIDE are not available. TOLBUTAMIDE is probably combustible.

Biological Activity

tolbutamide is a potent inhibitor of camp with an ic50 value of 4mm [1].tolbutamide has been reported to inhibit both the basal and the cyclic amp-stimulated protein kinase activites with an ic50 value of 4mm for cyclic amp-dependent kinase activity. in addition, tolbutamide has been revealed to inhibit both soluble and membrane-bound protein kinase from canine heart. moreover, the tolbutamide inhibition of adipose tissue cyclic amp- dependent protein kinase is explanation for antilipolytic effects [1]. besides, tolbutamide and dbcamp has been exhibited to increase about four-fold levels of cx43 mrna and decrease about 80% the expression of ki-67 [2].

Mechanism of action

Tolbutamide is one of the most widely used antidiabetic agents. Its action is preferably connected with stimulatory action of β-cells in the pancreas, which results in intensive insulin secretion.

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.

Safety Profile

Moderately toxic by ingestion and several other routes. A human teratogen. Human reproductive effects by ingestion and possibly other routes: stillbirth, developmental abnormalities of the cardlovascular (circulatory) system and urogenital system, and unspecified neonatal effects. Human systemic effects by ingestion: nausea or vomiting, hypoglycemia. Other experimental teratogenic and reproductive effects. Mutation data reported. Implicated in aplastic anemia. When heated to decomposition it emits very toxic fumes of NO, and SOx.

Synthesis

Tolbutamide, 1-butyl-3-p-toluenesulfonylurea (26.2.2), is made in a single step reaction by interaction of p-toluenesulfonylamide (in the form of sodium salt) with butylisocyanate.

Synthesis_64-77-7

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.

Metabolism

Tolbutamide is metabolised in the liver by hydroxylation mediated by the cytochrome P450 isoenzyme CYP2C9. It is excreted in the urine chiefly as inactive metabolites.

References

[1] wray hl, harris aw. adenosine 3', 5'-monophosphate-dependent protein kinase in adipose tissue: inhibition by tolbutamide. biochem biophys res commun. 1973 jul 2;53(1):291-4.
[2] sánchez-alvarez r1, paíno t, herrero-gonzález s, medina jm, tabernero a. tolbutamide reduces glioma cell proliferation by increasing connexin43, which promotes the up-regulation of p21 and p27 and subsequent changes in retinoblastoma phosphorylation. glia. 2006 aug 1;54(2):125-34.

98-59-9
64-77-7
Synthesis of TOLBUTAMIDE from Tosyl chloride

TOLBUTAMIDE Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 271)Suppliers
Supplier Tel Email Country ProdList Advantage
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21700 55
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29914 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293 sales@sdzschem.com China 2931 58
Hubei Jusheng Technology Co.,Ltd.
18871490254 linda@hubeijusheng.com CHINA 28180 58
Hubei xin bonus chemical co. LTD
86-13657291602 linda@hubeijusheng.com CHINA 22968 58
Chongqing Chemdad Co., Ltd
+86-023-61398051 +8613650506873 sales@chemdad.com China 39916 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427 sales@conier.com China 47465 58
Shaanxi Dideu Medichem Co. Ltd
+86-029-81148696 +8615536356810 1047@dideu.com China 3984 58
Antai Fine Chemical Technology Co.,Limited
18503026267 info@antaichem.com CHINA 9641 58
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 19892 58

View Lastest Price from TOLBUTAMIDE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
tolbutamide pictures 2021-10-20 tolbutamide
64-77-7
US $20.00 / KG 1KG 99% 9000kg/per week Hebei Lingding Biotechnology Co., Ltd.
Tolbutamide pictures 2021-07-13 Tolbutamide
64-77-7
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
Tolbutamide pictures 2021-07-10 Tolbutamide
64-77-7
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
  • tolbutamide pictures
  • tolbutamide
    64-77-7
  • US $20.00 / KG
  • 99%
  • Hebei Lingding Biotechnology Co., Ltd.
  • Tolbutamide pictures
  • Tolbutamide
    64-77-7
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd
  • Tolbutamide pictures
  • Tolbutamide
    64-77-7
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd
Pramidex Rastinon Restinon Sk-tolbutamide tarasina tolbet Tolbusal Tolbutamid tolbutamidum Tolbutol tolbutone Tolumid Toluvan Tolylsulfonylbutylurea u2043 U-2043 Urea, 1-butyl-3-(p-tolylsulfonyl)- Willbutamide LABOTEST-BB LT00772316 3-[P-TOLYL-4-SULFONYL]-1-BUTYLUREA 1-BUTYL-3-(P-TOLYLSULFONYL)UREA 1-BUTYL-3-(4-METHYLBENZENESULFONYL)UREA 1-BUTYL-3-(4-METHYLPHENYLSULFONYL)UREA 1-N-BUTYL-3-(P-TOLYLSULFONYL)UREA TOLUINA TOLBUTAMIDE TOLBUTAMIDE, [CARBONYL-14C] N-4-METHYLBENZENESULFONYL-N'-BUTYL UREA N-[(BUTYLAMINO)CARBONYL]-4-METHYLBENZENE-SULFONAMIDE 1-(([(Butylamino)carbonyl]amino)sulfonyl)-4-methylbenzene 1-Butyl-3-(para-tolylsulfonyl)-urea 1-Butyl-3-(para-tolysulfonyl)urea 1-Butyl-3-(p-methylphenylsulfonyl)urea 1-butyl-3-(p-tolylsulfonyl)-ure 1-Butyl-3-tosylurea 1-p-Toluenesulfonyl-3-butylurea Aglicid arcosal Arkozal Artosin Artozin n-((butylamino)carbonyl)-4-methyl-benzenesulfonamid n-(4-methylphenylsulfonyl)-n’-butylurea N-(4-Methylphenylsulfonyl)-N'-butylurea N-(n-Butyl)-N'-p-toluene-sulfonylurea N-(p-Methylbenzenesulfonyl)-N'-butylurea n-(p-tolylsulfonyl)-n’-butylcarbamide n-(p-tolylsulfonyl)n’-butylcarbamide N-(p-Tolylsulfonyl)-N'-butylcarbamide n-(sulfonyl-p-methylbenzene)-n’-butylurea n-(sulfonyl-p-methylbenzene)-n’-n-butylurea N-(Sulfonyl-p-methylbenzene)-N'-N-butylurea n-[(butylamino)carbonyl]-4-methyl-benzenesulfonamid diabesan Diabetamid Diabetol Diabuton Diasulfon