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T0318 Sigma

Tranilast

≥98% (HPLC), powder

Synonym: 2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino] benzoic acid, 3,4-DAA, N-(3,4-Dimethoxycinnamoyl)anthranilic acid, Rizaben, SB-252218

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Properties

Related Categories Approved Therapeutics/Drug Candidates, Arachidonic Acid Cascade, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology,
assay   ≥98% (HPLC)
form   powder
color   white to beige
mp   166.2-168.2 °C(lit.)
solubility   DMSO: >10 mg/mL
  H2O: insoluble
originator   Kissei
storage temp.   2-8°C
Gene Information   human ... VEGFA(7422), VEGFB(7423), VEGFC(7424)

Description

Application

The effect of Tranilast on mast cell surface receptors was studied in murine bone marrow-derived mast cells.1

Biochem/physiol Actions

Tranilast is an anti-asthma drug, which inhibits LTC4 and PGE2 formation in stimulated monocytes, but does not inhibit cyclooxygenase or lipoxygenase activity; inhibits mast cell degranulation; inhibits VEGF-induced angiogenesis in vivo and also inhibits proliferation and tube formation of human endothelial cells in vitro. Tranilast may represent a new class of drugs for therapy to treat ongoing TH1-mediated autoimmune diseases.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

This compound was developed by Kissei. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
WGK Germany 
3
RTECS 
DG8731000

Protocols & Articles

Peer-Reviewed Papers

References

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1. Pentagalloylglucose down-regulates mast cell surface FcepsilonRI expression in vitro and in vivo. Kageyama-Yahara N, Suehiro Y, Maeda F, et al. FEBS Lett. 584(1), 111-8, (2010)

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Treatment of autoimmune neuroinflammation with a synthetic tryptophan metabolite. Platten, M., et al. Science 310, 850-855, (2005)

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Modulation of human monocyte activities by Tranilast, SB 252218, a compound demonstrating efficacy in restenosis. Capper, E.A. J. Pharmacol. Exp. Ther. 295, 1061, (2000)

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Inhibitory mechanism of tranilast in human coronary artery smooth muscle cells proliferation, due to blockade of PDGF-BB-receptors. Watanabe, S., et al. Br. J. Pharmacol. 130, 307, (2000)

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Breast cancer stem-like cells are inhibited by a non-toxic aryl hydrocarbon receptor agonist. Prud'homme GJ, Glinka Y, Toulina A, et al. PLoS ONE 5(11), e13831, (2010)

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Tranilast treatment decreases cell growth, migration and inhibits colony formation of human breast cancer cells. Subramaniam V, Ace O, Prud'homme GJ, et al. Exp. Mol. Pathol. 90(1), 116-22, (2011)

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Neuropilin-1 is expressed by breast cancer stem-like cells and is linked to NF-κB activation and tumor sphere formation. Glinka Y, Mohammed N, Subramaniam V, et al. Biochem. Biophys. Res. Commun. 425(4), 775-80, (2012)

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Tranilast inhibits the function of cancer-associated fibroblasts responsible for the induction of immune suppressor cell types. Ohshio Y, Hanaoka J, Kontani K, et al. Scand. J. Immunol. 80(6), 408-16, (2014)

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Tranilast ameliorates impaired hepatic functions in Schistosoma mansoni-infected mice. Said E, Said SA, Elkashef WF, et al. Inflammopharmacology 20(2), 77-87, (2012)

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Case in which tranilast ophthalmic solution was thought to be effective for the prevention of symblepharon and recurrence after pterygium surgery. Tsuji A, Kawai K, Fan H, et al. Tokai J. Exp. Clin. Med. 36(4), 120-3, (2011)

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A pilot study of scheduled endoscopic balloon dilation with oral agent tranilast to improve the efficacy of stricture dilation after endoscopic submucosal dissection of the esophagus. Uno K, Iijima K, Koike T, et al. J. Clin. Gastroenterol. 46(9), e76-82, (2012)

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Tranilast prevents atrial remodeling and development of atrial fibrillation in a canine model of atrial tachycardia and left ventricular dysfunction. Nakatani Y, Nishida K, Sakabe M, et al. J. Am. Coll. Cardiol. 61(5), 582-8, (2013)

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Production of tranilast [N-(3',4'-dimethoxycinnamoyl)-anthranilic acid] and its analogs in yeast Saccharomyces cerevisiae. Eudes A, Baidoo EE, Yang F, et al. Appl. Microbiol. Biotechnol. 89(4), 989-1000, (2011)

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Recurrent epithelioid hemangioma: therapeutic potential of tranilast and indomethacin. Ogura K, Shinoda Y, Okuma T, et al. J. Orthop. Sci. 17(2), 194-8, (2012)

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Atypical clinical appearance of eosinophilic pustular folliculitis of seborrheic areas of the face. Matsumura Y and Miyachi Y Eur. J. Dermatol. 22(5), 658-62, (2012)

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Physicochemical and pharmacokinetic characterization of amorphous solid dispersion of tranilast with enhanced solubility in gastric fluid and improved oral bioavailability. Onoue S, Kojo Y, Aoki Y, et al. Drug Metab. Pharmacokinet. 27(4), 379-87, (2012)

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Suppression of human CD4+ T cell activation by 3,4-dimethoxycinnamonyl-anthranilic acid (tranilast) is mediated by CXCL9 and CXCL10. Hertenstein A, Schumacher T, Litzenburger U, et al. Biochem. Pharmacol. 82(6), 632-41, (2011)

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Mechanisms and interventions in peritoneal fibrosis. Tomino Y Clin. Exp. Nephrol. 16(1), 109-14, (2012)

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Stable dry powder inhaler formulation of tranilast attenuated antigen-evoked airway inflammation in rats. Kawabata Y, Aoki Y, Matsui T, et al. Eur. J. Pharm. Biopharm. 77(1), 178-81, (2011)

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Therapeutic potential of tranilast, an anti-allergy drug, in proliferative disorders. Rogosnitzky M, Danks R, and Kardash E Anticancer Res. 32(7), 2471-8, (2012)

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Tranilast: a pharmaceutical candidate for reduction of adhesions using a novel approach. Petrilli J, Wadsworth S, Cooper K, et al. Semin. Reprod. Med. 26(4), 341-8, (2008)

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Tranilast binds to aβ monomers and promotes aβ fibrillation. Connors CR, Rosenman DJ, Lopes DH, et al. Biochemistry 52(23), 3995-4002, (2013)

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Lupus miliaris disseminatus faciei successfully treated with tranilast: report of two cases. Koike Y, Hatamochi A, Koyano S, et al. J. Dermatol. 38(6), 588-92, (2011)

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Long-term follow-up after lamellar keratoplasty in a patient with bilateral idiopathic corneal keloid. Fukuda K, Chikama T, Takahashi M, et al. Cornea 30(12), 1491-4, (2011)

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Suppression of the allogeneic response by the anti-allergy drug N-(3,4-dimethoxycinnamonyl) anthranilic acid results from T-cell cycle arrest. Zaher SS, Coe D, Chai JG, et al. Immunology 138(2), 157-64, (2013)

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Biocompatibility and antifibrotic effect of UV-cross-linked hyaluronate as a release-system for tranilast after trabeculectomy in a rabbit model--a pilot study. Spitzer MS, Sat M, Schramm C, et al. Curr. Eye Res. 37(6), 463-70, (2012)

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Tranilast inhibits the cell growth of normal human keratinocytes in vitro. Kubo M, Zhao Y, and Moriguchi T Arch. Dermatol. Res. 304(9), 745-53, (2012)

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Pharmacological inhibition of coronary restenosis: systemic and local approaches. Guerra E, Byrne RA, and Kastrati A Expert Opin. Pharmacother. 15(15), 2155-71, (2014)

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High-dose tranilast administration to rats creates interstitial cystitis-like symptoms with increased vascular permeability. Nishijima S, Sugaya K, Kadekawa K, et al. Life Sci. 93(23), 897-903, (2013)

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Tranilast prevents the progression of chronic cyclosporine nephrotoxicity through regulation of transforming growth factor β/Smad pathways. Tao Y, Hu L, Li S, et al. Transplant. Proc. 43(5), 1985-8, (2011)

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Novel action of 3,4-DAA ameliorating acute liver allograft injury. Sun QF, Ding JG, Sheng JF, et al. Cell Biochem. Funct. 29(8), 673-8, (2011)

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Effect of TJN-331 on anti-Thy1 nephritis in rats via inhibition of transforming growth factor-β1 production. Saegusa Y, Sadakane C, Koseki J, et al. Biol. Pharm. Bull. 33(10), 1710-5, (2010)

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Tranilast could has potential therapeutic value in the treatment of psoriasis. Mansouri K, Motlagh HR, and Keshavarz M Med. Hypotheses 76(2), 217-9, (2011)

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Tranilast attenuates TGF-β1-induced epithelial-mesenchymal transition in the NRK-52E cells. Li SS, Liu QF, He AL, et al. Pak. J. Pharm. Sci. 27(1), 51-5, (2014)

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Tranilast and hypertensive heart disease: further insights into mechanisms of an anti-inflammatory and anti-fibrotic drug. Pfab T and Hocher B J. Hypertens. 22(5), 883-6, (2004)

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Merck 14,9570

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