Tranilast

Trade Name Manufacturer Country Year Introduced 

Aoyagi, T., Miki, T., Kadoya, S., Inaoka, M. and Shindo, M. U.S. Patent 3,499,925 March 10,1970 assigned to Daiichi Seiyaku Company Limited, Japan and Mitsubishi Chemical Industries Limited, Japan 

Chemical Name 2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl] amino] -benzoic acid Common Name — 

4 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 tor 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, he 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. 

---

Phentermine HCI Vinblastine sulfate Vincristine sulfate Benzene sulfonyl chloride Glybuzole Glymidine Tranilast... 

One of the early steps in an allergic reaction consists in the release of a series of endogenous compounds referred to as mediators from sensitized cells. The finding in the early 1960s that cromolyn sodium, still the only approved drug of this class, blunts this reaction has led to an intense search for additional examples. It is of interest that a relatively simple anthranilic acid derivative has shown mediator-release inhibiting activity. Reaction of 3,4-dimethoxybenzalde-hyde (167) with isatoic anhydride 168 gives the condensation product 169, which, upon hydrolysis, affords tranilast (170) (43]. 

Tieabesone propionate, 75 TUomisole, 217 Timefurone, 208 Timobesone acetate, 75 Tinabinol, 210 Tipentosin, 129 Tipredane, 74 Tiprinast, 173 Tixocortol pivalate, 73 Tolgabide, 47 Tolrestat, 56 Tomoxetine, 30 Tranexamie acid, 6 Tranilast, 44 Transcainide, 112 Trepipam, 146,147 Trifenagrel, 89 Trimetrexate, 149 Tripamide, 51 Triprolidine, 105 Tropanserin, 39 Tubulozole, 91... 

Kawashima, Y., et al. 1991. Preparation of multiple unit hollow microspheres (microballons) with acrylic resin containing tranilast and their drug release characteristics in vitro) and floating behavior in vivo). J Control Release 16 279... 

Shishibori T, Oyama Y, Matsushita O, Yamashita K, Furuichi H, Okabe A, Maeta H, Hata Y, Kobayashi R. 1999. Three distinct anti-allergic drugs, amlexanox, cromolyn and tranilast, bind to S100A12 and S100A13 of the S100 protein family. Biochem J 338 ( Pt 3) 583-589. 

Yamada H, Tajima S, NishikawaT, Murad S, Pinnell SR. Tranilast, a selective inhibitor of collagen synthesis in human skin fibroblasts. Journal of Biochemistry 1994, 116,... 

Omega-3 fatty acids Warfarin Antiallergic drugs Tranilast... 

Oral agents in this category include corticosteroids, nonsteroidal inflammatory drugs, statins, and tranilast. 

Tranilast Inhibits SMC migration and proliferation, decreases collagen synthesis TREAT (25) TREAT-2 (26) PRESTO (27) Lower restenosis Lower restenosis No difference... 

Abbreviations CDK, cyclin-dependent kinase CREST, cilostazol for restenosis trial MACE, major adverse cardiac events ORAR, oral rapamycin to prevent restenosis ORBIT, oral rapamune to inhibit restenosis REAR, peroxisome proliferator-activated receptor PRESTO, prevention of restenosis with tranilast and its outcomes SMC. smooth muscle cell ThR, target lesion revascularization tREAT, Tranilast restenosis following angioplasty trials TVR, target vessel failure. ... 

Tamai H, Katoh O, Suzuki S. Impact of tranilast on restenosis after coronary angioplasty Tranilast Restenosis Following Angioplasty Trial (TREAT) Am Heart J 1999 138 968- 975,... 

Holmes DR, Savage M, LaBlanche JM, et al. Results of Prevention of REStenosis with Tranilast and its outcomes (PRESTO) Trial. Circulation 2002 106 1243-1250. 

Kao J, Tobis J, McClelland RL, et al. Investigators in the Prevention of Restenosis with Tranilast and its Outcomes Trial. Relation of metformin treatment to clinical events in diabetic patients undergoing percutaneous intervention. Am J Cardiol 2004 93 1347-1350, A5. 

Those that have been identified in recent times include flavonoids,212-214 aurothiomalate,215 hydrangenol,216 occurring in the leaves of Hydrangea, tannins,217 derivatives of tranilast,218 curcumin,219 an extract of the spice turmeric, glycyrrhizin,220 found in the roots and rhizomes of licorice (Glycyrrhiza glabra), used as an effective antiinflamatory agent in Chinese medicine. 

Kakegawa, H. et al., Hyaluronidase-inhibitory and anti-allergic activities of the photo-irradiated products of tranilast, Chem. Pharm. Bull., 33, 3738, 1985. 

---