6054-98-4
disodium 5,5'-azodisalicylate
CAS: 6054-98-4
Molecular Formula: C14H8N2O6.2Na
6054-98-4 - Names and Identifiers
| Name | disodium 5,5'-azodisalicylate |
| Synonyms | Olsalazine disodium disodium 5,5'-azodisalicylate 5,5'-Azobissalicylic acid disodium salt 5,5′-Azobis(salicylic acid, sodium salt) 3,3'-azobis[6-hydroxy-benzoicacidisodiumsalt 5,5'-Azobis(2-hydroxybenzoic acid sodium) salt Benzoicacid,3,3'-azobis[6-hydroxy-,disodiumsalt disodium 3,3'-(E)-diazene-1,2-diylbis(6-hydroxybenzoate) 4,4′-Dihydroxyazobenzene-3,3′-dicarboxylic acid disodium salt disodium 5-[(2Z)-2-(3-carboxylato-4-oxocyclohexa-2,5-dien-1-ylidene)hydrazino]-2-hydroxybenzoate |
| CAS | 6054-98-4 |
| EINECS | 227-975-7 |
| InChI | InChI=1/C14H10N2O6.2Na/c17-11-3-1-7(5-9(11)13(19)20)15-16-8-2-4-12(18)10(6-8)14(21)22;;/h1-6,17-18H,(H,19,20)(H,21,22);;/q;2*+1/p-2/b16-15+; |
6054-98-4 - Physico-chemical Properties
| Molecular Formula | C14H8N2O6.2Na |
| Molar Mass | 346.2 |
| Melting Point | 240 °C |
| Solubility | Soluble in water, and DMSO. |
| Appearance | neat |
| Color | Light Yellow to Yellow |
| Storage Condition | Inert atmosphere,Store in freezer, under -20°C |
| In vitro study | Olsalazine showed pleiotropic effects on intestinal electrolytes. In vitro application of Olsalazine (< 2.89 mM) simultaneously increased the secretion of sodium and chloride ions and increased the absorption of chloride ions in the ileum mucosa of rats and rabbits. Concentrations of Olsalazine <11.5 mM also dose-dependently reduced net sodium and, to a greater extent, chloride absorption in the isolated rat colon. The secretion of potassium increased only at high Olsalazine concentrations (11.5 mM). Olsalazine also inhibited glucose and lactose absorption in the isolated rat jejunum. Olsalazine is a potent inhibitor of LTB4 chemotaxis in human intestinal macrophages with an IC50 of 0.39 mM. Olsalazine (0.4 mM) inhibited phorbol ester (PMA)-activated neutrophils, or the superoxide radical product produced by the xanthine-xanthine oxidase reaction, reducing it by 31% and 73%, respectively. Other possible mechanisms by which mesalazine derived from Olsalazine may improve colonic mucosa/inflammation are inhibition of platelet activating factor, inhibition of cytokine production in human monocytes, inhibition of colonic fatty acid oxidation, inhibition of endothelial cell proliferation by folic acid antagonism, inhibition of arachidonic acid synthesis of leukotrienes by inhibition of lipoxygenase, regulation of prostaglandin properties by action on prostaglandin 15-hydroxy dehydrogenase and interference with leukocyte function. |
| In vivo study | After oral administration, Olsalazine becomes a means of delivering mesalazine to the colon as few of the parent molecules are absorbed from the gastrointestinal tract. In the colon, azoreductase bacteria cleave the azo bond, releasing 2 molecules of mesalazine, demonstrating a therapeutic effect on inflammatory bowel disease. In nu/nu CD-1 mice with dextran sulfate sodium-induced experimental colitis, Olsalazine (50 mg/kg/day) significantly prolonged survival. In rodent models with colon cancer, Olsalazine inhibits tumor growth. In 1,2-dimethylhydrazine-treated rats, Olsalazine (25 mg/kg/day) reduced the number of tumors by 58.17 and the volume of tumors by 62.67, respectively. Administration of Olsalazine induced a 1.7-fold increase in the number of apoptotic cells, accompanied by a decrease in the rate of cell proliferation by 42.4. |
6054-98-4 - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| drugs for acute and chronic colitis | olsalazine sodium it is a drug for the treatment of acute and chronic colitis developed by PharmaciaA B Co., Switzerland. It was first marketed in Denmark in 1989. European Pharmacopoeia 7. 0 edition and national drug standard WS1-( X-349) -2004Z have been collected. A prodrug of olsalazine sodium consisting of an azo bond linking two 5-aminosalicylic acids. Bacteria in the colon split the diazonium bond, releasing 5-aminosalicylic acid; 5-aminosalicylic acid acts on the colitis mucosa, inhibiting the formation of prostaglandins, Leukotrienes and other inflammatory factors, and weakening cell membrane permeability, and play a role in the treatment of ulcerative colitis. This product weakens the absorption of nitrogen, sodium and water in the ileum and colon mucosa. In the human body, this absorption is converted into secretion. Ulcerative colitis patients taking this product 1g per day, the entire intestinal transmission time is about 40% shorter. One oral administration of 2g of this product to healthy subjects had no effect on the frequency of intestinal migration complex, but it could cause Diarrhea in 30% of the patients and aggravate Diarrhea of the patients with intestinal inflammation. Systemic bioavailability is very low, the absorption rate of oral dose is less than 5%. After absorption, about 10% of the dose was conjugated to olsalazide O-sulfate, t1/2 was about 1H, and the Half-Life of the conjugate was about 7 days. Figure 1 structural formula of olsalazine sodium |
| adverse reaction | The most common side effect was Diarrhea, the incidence was 17%. The usual Diarrhea difference between transient and intestinal inflammation is that the excretion is high in water, not bloody, and is related to the size of the dose, usually occurring at the beginning of treatment or at an increased dose. Reduce the amount of this product or combined with Loperamide, Diarrhea will be controlled. Other side effects are Head Pain, Nausea, Abdominal Pain, rash, dizziness and Arthralgia, the sulfasalazine allergy or intolerance of patients, the majority of this product can tolerate, taking sulfasalazine infertility men, the symptom was improved after using this product. |
| Use | for ulcerative colitis. |
| dosage | for active severe intestinal inflammation, usually 1-3g per day (starting with low dose), divided into 3 to 4 times, while eating; For chronic ulcerative colitis, the maintenance dose of 1g per day. (2016-03-11) |
| biological activity | Olsalazine Sodium is an anti-inflammatory prodrug comprising two 5-ASA moieties linked by azo bonds. |
Last Update：2024-04-09 15:16:51
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View History
6054-98-4
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