5-Aminosalicylsure

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H315：Verursacht Hautreizungen.

  H319：Verursacht schwere Augenreizung.

  H335：Kann die Atemwege reizen.

• Sicherheit

  P261：Einatmen von Staub vermeiden.

  P264：Nach Gebrauch gründlich waschen.

  P264：Nach Gebrauch gründlich waschen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P304+P340：BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.

  P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

  P405：Unter Verschluss aufbewahren.

5-Aminosalicylic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

• S-Sätze Betriebsanweisung:

  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
  S24/25:Berührung mit den Augen und der Haut vermeiden.

• Beschreibung

  5-Aminosalicylic acid (5-ASA), also known as mesalazine or mesalamine, is a metabolite and potential pharmacologically active component of sulphasalazine, a drug used in the treatment of Crohn’s disease and ulcerative colitis. However, the mechanism by which this drug works has not been established. In whole blood assays, 5-ASA proves to be a weak, non-selective inhibitor of both COX-1 and COX-2 with IC50 values of 410 and 61 μM, respectively. In ionophore-stimulated colonic mucosal cells, 1 mM 5-ASA does not inhibit prostaglandin E2 (PGE2) production, but does reduce leukotriene B4 (LTB4) synthesis approx. 50%. In ionophore-stimulated human leukocytes, 400 μM 5-ASA reduces LTB4 production approximately 20%. 5-ASA does not inhibit 15-hydroxy PGDH at concentrations up to 50 μM.

• Chemische Eigenschaften

  Off-White to pink crystals, melting point about 280 ℃ (decomposition). Soluble in hydrochloric acid, slightly soluble in hot water, and slightly bath in cold water or ethanol. In the manufacture of light-sensitive paper, azo and sulfur dyes.

• Originator

  Radcliffe Infirmary (United Kingdom)

• Verwenden

  5-Aminosalicylic acid is used in the preparation of gastrointestinal anti-inflammatory agents. It is a metabolite of sulfasalazine. It acts as a drug involved in the treatment of Crohn's disease and ulcerative colitis. Further, it is used to make dyes and light-sensitive papers.

• synthetische

  Preparation by reduction of m-nitrobenzoic acid with Zn dust and HCl.

• Application

  5-Aminosalicylic acid (5-ASA) has been used to synthesize 5-formyl-aminosalicylate-inulin to quantify its release during in vitro digestion and fermentation and compare the in vitro fermentation properties of the conjugated inulin to native inulin. It is also used in cell adhesion assay to study its effects on E-cadherin glycosylation and membranous turnover. This compound is used to evaluate its effects on the neutrophilic inflammation index (NII) phenotype to study the effectiveness of the high cholesterol diet-gut inflammation (HCD-GI) platform. 5-Aminosalicylic acid is a peroxidase substrate suitable for use in ELISA procedures. This substrate produces a soluble end product that is brown in color and can be read spectrophotometrically at 450 nm. The reaction may be stopped with 3 N NaOH and read at 550 nm.

• Definition

  ChEBI: Mesalamine is a monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position. It has a role as a non-steroidal anti-inflammatory drug. It is an aromatic amine, an amino acid, a member of phenols, a monocarboxylic acid and a monohydroxybenzoic acid. It is functionally related to a salicylic acid. It is a conjugate acid of a mesalaminate(1-).

• Manufacturing Process

  Procedure A: To 5-nitrosalicylic acid potassium salt (55 g, 246 mmol) dissolved in water (200 mL) was added potassium hydroxide pellets to reach pH 11.5. To this solution 2 g of Raney nickel were added. The mixture was heated-up to reflux and hydrazine hydrate (40 mL, 80% in water, 64 mmol) was added dropwise during 3-4 hrs. The reflux was maintened until HPLC showed the disappearance of the starting material and the complete reduction of 5-nitrosalicylic acid (3-4 hrs). The hot mixture was filtered under nitrogen and the solution was collected. The solution was cooled to 40°C and the pH was adjusted to 2.3 by addition of 35% HCl aqueous solution. The precipitation of 5-aminosalicylic acid occurred. The solution was cooled at 0°C, and after standing at this temperature for 2 hr, the precipitate was filtered, washed with water, and dried at 60-70°C. 5-Aminosalicylic acid was obtained in 89% yield.
  Procedure B: To 5-nitrosalicylic acid potassium salt (55 g, 246 mmol) dissolved in water (200 mL) was added potassium hydroxide pellets to reach pH 11.5. The solution was charged in a stainless steel autoclave and 2 g of Raney nickel are added. Hydrogen was introduced into the autoclave reaching a pressure of 8 atm. The mixture was heated-up to 100°C. The temperature was maintained until HPLC-test 5-aminosalicylic acid showed the disappearance of the starting material and the complete reduction of 5- aminosalicylic acid (6-8 hrs). Hydrogen was purged and replaced by nitrogen. The hot mixture was filtered under nitrogen, the filtrate was cooled to 40°C, and the pH was adjusted to 2.3 by addition of 35% HCl aqueous solution. The precipitation of the 5-aminosalicylic acid occurred. The solution was cooled at 0°C, and after standing at this temperature for 2 hr, the precipitate was filtered, washed with ion depleted water, and dried at 60-70°C.

• Trademarks

  SALOFALK

• Therapeutic Function

  Antibacterial

• Allgemeine Beschreibung

  Odorless white to pinkish crystals or purplish-tan powder. Aqueous solutions acidic (pH approximately 4.1 at 0.8 mg/L water) .

• Air & Water Reaktionen

  Sensitive to moisture. Water insoluble.

• Reaktivität anzeigen

  5-Aminosalicylic acid is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizers.

• Brandgefahr

  Flash point data for 5-Aminosalicylic acid are not available; however, 5-Aminosalicylic acid is probably combustible.

• Flammability and Explosibility

  Non flammable

• Biochem/physiol Actions

  5-Aminosalicylic acid (5-ASA) is a first-line medicine, used to treat inflammatory bowel diseases like ulcerative colitis (UC). It has a high-efficiency rate in maintenance and induction of remission. 5-ASA is an active component of sulfasalazine and also consists of the carbohydrate polymer, inulin. It might exhibit anti-oxidant activity to lessen tissue injury. 5-ASA is vital for the prevention of T cell activation and proliferation. It negatively regulates cyclooxygenase and lipoxygenase pathways and lowers the formation of prostaglandins and leukotrienes. 5-ASA stimulates the membranous expression of E-cadherin and boosts intercellular adhesion.

• Clinical Use

  Induction and maintenance of remission in ulcerative colitis

• Sicherheitsprofil

  Poison by intraperitoneal route.Moderately toxic by ingestion. Human systemic effects byingestion: hypermotility, diarrhea, dermatitis, increasedbody temperature. When heated to decomposition it emitstoxic fumes of NOx.

• Stoffwechsel

  The absorbed part of mesalazine is almost completely acetylated in the gut wall and in the liver to acetyl-5- aminosalicylic acid. The acetylated metabolite is excreted mainly in urine by tubular secretion, with traces of the parent compound.

• läuterung methode

  It crystallises as needles from H2O containing a little NaHSO3 to avoid aerial oxidation to the quinone-imine. The Me ester gives needles from *C6H6, m 96o, and the hydrazide has m 180-182o (from H2O). [Fallab et al. Helv Chim Acta 34 26 1951, Shavel J Amer Pharm Assoc 42 402 1953, Beilstein 14 IV 2058.]

5-Aminosalicylic acid Upstream-Materialien And Downstream Produkte

5-Aminosalicylsure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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