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Tranilast

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Tranilast Basic information
Tranilast Chemical Properties
  • Melting point:166.2-168.2 °C(lit.)
  • Boiling point:465.23°C (rough estimate)
  • Density 1.3185 (rough estimate)
  • refractive index 1.5100 (estimate)
  • storage temp. 2-8°C
  • solubility DMSO: 18 mg/mL
  • form powder
  • pka3.47±0.36(Predicted)
  • color white to beige
  • Merck 14,9570
  • InChIKeyNZHGWWWHIYHZNX-CSKARUKUSA-N
  • CAS DataBase Reference53902-12-8(CAS DataBase Reference)
Safety Information
  • Hazard Codes Xn
  • Risk Statements 22
  • Safety Statements 26-36
  • WGK Germany 3
  • RTECS DG8731000
  • ToxicityLD50 in male, female mice, male, female rats (mg/kg): 780, 680, 1600, 1100 orally; 410, 385, 405, 395 i.p.; 2630, 2820, 3630, 3060 s.c. (Nakazawa, p 385)
MSDS
Tranilast Usage And Synthesis
  • Chemical PropertiesPale Green Solid
  • OriginatorRizaben,Kissei Pharmaceutical Co., Ltd.,Japan,1982
  • UsesAntiallergic drug, used to treat bronchial asthma, allergic rhinitis and atopic dermatitis.
  • Usescoronary vasodilator
  • UsesTranilast is a compound that exhibits anti-inflammatory and immunomodulatory effects by inhibiting lipid mediator and cytokine release from inflammatory cells and interfering with PDGF- and TGF-β1-induced proliferation and migration of vascular medial smooth muscle cells. Tranilast suppresses production of prostaglandin D2 (IC50 = 0.1 mM), prostaglandin E2 (IC50 = ~1-20 μM), thromboxane B2 (IC50 = ~10-50 μM), TGF-β1 (IC50 = ~100-200 μM), and interleukin-8 (IC50 = ~100 μM) in in vitro models as well as attenuates of the proinflammatory activity of human monocytes. While originally marketed as an antiallergenic drug, the efficacy of tranilast in preventing restenosis after percutaneous coronary intervention has been tested in a large-scale clinical trial. Additionally, tranilast inhibits VEGF-induced angiogenetic activities (i.e., proliferation, migration and tube formation of vascular endothelial cells) with IC50 values of 22, 18 and 193 μM, which may prove therapeutic for various retinal diseases.[Cayman Chemical]
  • DefinitionChEBI: An amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 3,4-dimethoxycinnamoyl group.
  • Manufacturing Process4 g of 3,4-dimethoxycinnamic acid was dissolved in 20 ml of dry pyridine. To this solution were added under cooling with ice and agitation 2 g of benzenesulfonyl chloride whereby a red orange precipitate was formed. The reaction mixture was stirred for about one hour and then 2 g of methyl anthranilate were added to the mixture under cooling with ice. The mixture was stirred for 2 hours at room temperature to complete the reaction. After completion of the reaction, the reaction mixture was concentrated and the residue was taken up in about 10 ml of chloroform. The solution was washed first with a 10% aqueous solution of caustic soda, then with a 10% aqueous solution of hydrochloric acid and finally with water and then distilled to remove chloroform whereby crystals of N-(3',4'-dimethoxycinnamoyl)- anthranilic acid methyl ester were obtained.
    This product was dissolved in 10 ml of chloroform. To this solution were added 10 ml of a 10% aqueous solution of caustic soda and the mixture was warmed at 50°C to effect hydrolysis of the ester group. After completion of the reaction, the organic phase was separated, washed with water and distilled to remove the solvent whereby 2.1 g (yield: 48%) of the end product, i.e., N- (3',4'-dimethoxycinnamoyl)-anthranilic acid, were obtained. This product had a melting point of 211°C to 213°C
  • Therapeutic FunctionAntiallergic
  • Biological ActivityAntiallergic via inhibition of chemical mediator release from mast cells. Most recently shown to be an effective inhibitor of angiogenesis. Demonstrated to antagonize the effects of angiotensin II on human arteries, possibly by an interaction at the level of the AT 1 receptor.
Tranilast Preparation Products And Raw materials
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