Tolbutamid

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H302：Gesundheitsschädlich bei Verschlucken.

  H317：Kann allergische Hautreaktionen verursachen.

• Sicherheit

  P261：Einatmen von Staub vermeiden.

  P321：Besondere Behandlung

  P333+P313：Bei Hautreizung oder -ausschlag: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

TOLBUTAMIDE Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
  R40:Verdacht auf krebserzeugende Wirkung.
  R43:Sensibilisierung durch Hautkontakt möglich.

• S-Sätze Betriebsanweisung:

  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.

• Chemische Eigenschaften

  White or almost white, crystalline powder.

• Originator

  Dolipol,Hoechst,France,1956

• Verwenden

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

• Verwenden

  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.

• Verwenden

  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

• Allgemeine Beschreibung

  White crystals.

• Allgemeine Beschreibung

  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.

• Allgemeine Beschreibung

  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.

• Air & Water Reaktionen

  Insoluble in water.

• Reaktivität anzeigen

  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. .

• Brandgefahr

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

• Biologische Aktivität

  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.

• Sicherheitsprofil

  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.

• Synthese

  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.

  

• Arzneimittelwechselwirkung

  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.

• Stoffwechsel

  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.

• Einzelnachweise

  [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.

TOLBUTAMIDE Upstream-Materialien And Downstream Produkte

Tolbutamid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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